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Gapers Block published from April 22, 2003 to Jan. 1, 2016. The site will remain up in archive form. Please visit Third Coast Review, a new site by several GB alumni.
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Friday, September 29

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Andrew / February 15, 2006 11:07 AM

Blind-ish date with a woman who worked at a vendor to my company. We went to see "Something to Talk About," which looked like a romantic comedy but turned out to be about the messy break-up of a marriage (with some funny moments, but still). Not a great date flick.

There was a thunderstorm brewing as we left the theater, and she asked, in total seriousness, what thunder was. "Is it, like, angels stomping around?" She really didn't know.

gretchen / February 15, 2006 11:23 AM

I had a concert date with a guy I been out with a few times, a friend of a friend.

When I showed up at his place, he was completely drunk because apparently it was a bank holiday which he translated as "party your butt off" because he had a free day from work. I was completely sober.

When the music started he proceeded to dance in insane ways and attempted to get me to do the same by holding me and jumping up and down, oblivious to the tears in my eyes. It was so uncomfortable.

Needless to say we didn't go out again after that. I heard through the pipeline he was rather embarrassed.

shechemist / February 15, 2006 11:24 AM

a first breakfast date with a guy that responded to my personal ad. 10 mins into the date he started talking about his daughter. ok cool. I don't have a problem with that. and then he looked at me and said that he was ready to have a son now.

check please.

MikeH / February 15, 2006 11:32 AM

My worste date was my own fault. I took an attractive woman out a couple of years ago, where we ended up sharing a bottle of wine over dinner. Now, usually, I know better and switch to another form of alcohol after eating, because too much vino puts me right to sleep...

So we grabbed some drinks at a bar afterwards, where she proceeded to order me another glass of wine before I could stop her. Next thing I knew, and QUITE a few glasses of wine later, I was vaguely aware of slipping into la-la-land, before my date prodded me awake and suggested that maybe I should catch a taxi home...

The ladies were just lining up after that one, lemme tell ya...

j / February 15, 2006 11:36 AM

The worst one...

I met this lovely girl and we proceeded to go out for some dinner at her favorite restaurant. She was funny, goregous, smart, and really into me. I was charming, hillarious, and totally into her. It was at the risk of sounding silly, kismet. We were totally in sync, nerding out over the same stuff, finishing eachother's scentences. We totally got eachother. We closed out the restaurant and ended up spending the night up till 3am talking and totally enamoured. On the ride home I married her over and over, dreamed up our home, named our kids, planned our anniversaries... It goes without saying that I had totally fallen in love at first sight.

I spoke to her many times and the conversation was indeed amazing; we were totally into eachother and smitten. And despite all attempts, she didn't have time, wouldn't have time, or just couldn't make time for me.

I never saw her again.

And so the best date of my life, the date on which I though I had met my love, my future wife, my other, ended up being the date that broke my heart and as such the worst date I've ever been on.

DCE / February 15, 2006 11:49 AM

The conversation invariably turned to politics.

She: I'm a Republican. Sometimes I volunteer for campaigns and various issues.

Me: Awkward silence . . .

eep / February 15, 2006 11:56 AM

It was our third date. We were walking through a park, at which point he tackled me from behind, pinned me to the ground and tried to make out with me, all the while rubbing his erection against my leg. This was also the same date when the guy pretended to punch me in the face to get me to stop talking, his fist stopping mere inches from my nose.

I couldn't end the date fast enough.

kate / February 15, 2006 12:04 PM

Dinner hit a sour note after he talked about his love of god and how his mom is moving to some Central American country to do mission work... then he asked me about god and I said "I prefer not to talk about politics or religion in polite company" - to which he responded "OooOOOhhh! Touchy subject for ya?" ... so yeah. After an awkward-but-not-horrific dinner, we went to a bar. I figured if he got annoying he'd be easier to ignore or if it came down to it - ditch. It was a Saturday night so the bar was fairly crowded and when he got up to go to the bathroom, someone squeezed into his spot to order a drink. Pretty common behavior. My date came back from the bathroom just as the drink orderer had gotten his drink and was maneuvering out of the spot. Date asked in a nasty accusatory tone "Friend of yours?" Uhh.. whatever. Happened again, date had to pee, somebody else came in to order a drink. This time, date didn't even wait for drink-orderer to leave, he just reached over the guy, slammed the rest of his beer, slammed the glass on the bar, threw down a tip and STORMED outta the bar. ...huh?

supercrazyanonymous / February 15, 2006 12:30 PM

I went out with a guy on a blind date who took me out on the water and proceeded to take a lot of drugs and pass out. I was on the lake for 6 hours before he woke up and drove me back to dock at 3am.

amyc / February 15, 2006 12:38 PM

Nothing too traumatic, but I knew within five minutes when my date said she didn't know "what the big deal was about the Beatles" and "only listens to dance music" that this was not the girl for me. Who only listens to one kind of music? And if you only like one -- really, dance music?

Andy / February 15, 2006 12:39 PM

My worst "date" is not so much a singular event but a string of tepid, not-so-great but not terrible dates that have not led to any significant connection, intimacy or most importantly, SEX.

Leah / February 15, 2006 12:51 PM

Just one worst date?

The guy who didn't mention he was a midget or that he lived out of state.

The guy who looked at a $13 Goden Nugget bill and said, "Ooh, that's expensive. I've got seven dollars."

The guy who told me, "Admit it, if we'd met in person you never would have gone out with me. White women won't go on dates with asian men." Yet, there I was--a white woman on a date with an asian man who I knew was asian when I agreed to the date.

The guy who said, "If the office calls, I might have to go and harvest a brain."

The guy who read my entire blog before our first date. I said, "This one time in Rome..." and he said, "Oh, yeah, that was a funny, I read all about it." Leaving me with no stories to tell.

Bittersweetandsour / February 15, 2006 12:56 PM

My worst date ever never actually happened.

I had been talking to this guy over the internet and suggested we meet. But then I thought twice and decided against it, which I conveyed quite clearly. On my way home, via the "L", I missed five calls from him. Each voicemail he left got increasingly more erratic and the last one he left was "I'm not easily bothered by things, but YOU ARE MAKING ME VERY ANGRY".

I was sort of scared for my life at that point and since we had earlier decided to meet at a coffee shop near my apartment (before I cancelled), I had my best friend pick me up in my alley and I slept at her place.

The next day he wrote me a very psychotic email.

I'm glad we never met and therefore did not have the worst date ever.

boyswillbe / February 15, 2006 1:09 PM

This one was pretty bad. Sadly, it's not the worst date I've ever had.

J / February 15, 2006 1:34 PM

a couple sour dates with ladies who could both go by Miss Represent.

third meeting - halfway into a nice dinner she starts talking about how she's unable to getaway for a great travel opprtunity later in the month because of concrete weekend plans.
me: like what?
her: oh...i'm throwing a 30th birthday party...for my boyfriend.
me: are we not on a date right now?
her: i'm so embarassed.

second meeting - after meeting new year's eve, expressing an unmistakable interest, flattering her repeatedly, expressing excitement at hanging out and showering her with compliments, we meet at a bar, have a great time, flirting, really get into a rhythm, enjoying the moment. we close the bar, i'm walking her home and as we literally get to her door, she says, 'i probably should have told you this earlier, but i'm sort of seeing someone.'

ladies, if you're taken, please let us know right away. not that we're only interested in one thing, but it helps to know the possibilities. it doesn't matter how silly a way you work it in. try this at a bar, 'oh, you're drinking beer. my boyfriend loves beer!' whatever, just let us know the lay of your land. cheers.

snerdb / February 15, 2006 1:52 PM

my first date was my worst.

i was the biggest nerd in school in junior high and a total social pariah. so freshman year of high school i'd never been on a date, never held hands, never had a boyfriend. somehow a friend of mine (who was pretty and popular *and* smart, which was kind of amazing) managed to get her boyfriend to ask his friend to ask me to the homecoming dance. his friend was the boy i'd had a major, enormous crush on for about 4 years.

so a lot of it was totally awkward and cringeworthy, of course, but i got acclimated and we ended up having some good conversation, and a pretty fun time. i couldn't dance, so that part sucked, but all in all i enjoyed myself.

then they dropped me off (we all drove together) and he tried to kiss me goodnight. i'd never kissed anyone before, and i just kind of kept my lips shut and pressed them against his, and it had to have been the single worst kiss ever in the history of the world.

i was still kind of elated and amazed by the whole thing the next day, and i assumed we'd be a couple and go on dates and hold hands and all that, but he wouldn't talk to me in band on monday and avoided me like the plague after that. i heard from some people he made fun of the attempted kiss, as well.

luckily the next year i went to a high school with dorms where people didn't really date, just hooked up whenever possible. a much better system.

Harry Whittington / February 15, 2006 1:56 PM

I went quail hunting with Dick Cheney and he shot me in the face.

Mary Todd / February 15, 2006 2:00 PM

My worst date was on a Friday in April years and years ago.

I went with my husband to Ford's Theatre. There was a gentleman interrupting us and we only saw part of the show.

Worst date I have ever been on.

Emerson Dameron / February 15, 2006 3:05 PM

When we first got to Chicago, I tried to take my then-girlfriend to the movies. I didn't have the busses figured out, and we ended up standing at Clybourn and Damen for an hour. I didn't have the city figured out in general - who'da thunk the movies would be sold out on Valentine's? We split not long afterward.

Leelah / February 15, 2006 3:10 PM

It was an internet date, and I was the first to arrive. The little bar where we were meeting, was pretty crowded, so I took a seat at a cocktail table. My date arrived and he was absolutely adorable, but the first thing he did was complain that we were at a table because he "usually drinks for free at the bar." Bad sign.

After about two minutes of painful conversation... he mostly talked about how he "knows everyone" that went to this bar... it was blatantly obvious that this was going to be a long night. As a teacher, I like to think I'm skilled at getting people to talk, and this guy had nothing to say... hobbies? travel? music? Nothing. Work? I never did find out what he did for a living. When I first asked him, he said, "I'm unemployed". His profile said sales/marketing, so I assumed he had recently lost his job. I was operating under the unemployed assumption until some friends of his "from work" showed up at the bar.

The friends from work were from Russia, and after he greeted them, they asked us to join them... and so we did. I was relieved to be around some people who might actually be able to carry on a conversation.

The Russians, whose names I forgot almost immediately, weren't very interesting either... they'd only known my date for a month, and they'd only been in Chicago for the same amount of time. I tried asking about Moscow, places they'd been in the US... nothing. All three of them then proceeded to joke about work stuff... and I STILL had no idea what any of them did for a living. In the meantime, my date was getting more and more drunk? I quietly sipped my Chianti and kept a giant fake smile plastered on my face as I focused on the Bulls game on the TV, wishing I cared about basketball for once in my life.

As my date got progressively more wasted, he apparently decided that he liked me, and started putting his hands on my legs and back, and giving me weird compliments (if you can call them as such). "You have a great nose, " he slurred and then later, "You're modest." I couldn't figure that one out, and he finally explained that it was because I put "average" down for my body type on my profile.

An hour had passed, and I knew it was time to go, but right before I was able to escape, one of the Russians said they wanted cigarettes, and my inebriated date offered to go get them. In an instant, he put on his coat, and vanished.

There I was in this bar, knowing I couldn't just take off, with a couple of Russians who didn't have much of anything to say to me. It wasn't very comfortable, but we managed to talk weakly about Chicago for the ten minutes that my date was gone.

When he returned, I immediately wrapped myself in my coat and made a move to leave. The check came, and I handed him $20 for my two glasses of wine (more than enough). He took it, then pulled out a credit card, and paid for everyone... EXCEPT ME!!!! Not only did he keep my $20, but he didn't even offer to give me any change!!! At this point, I was almost laughing in his face.

The Russians walked out, and I scrambled after them. The date stopped me, grabbed me and hugged me, saying he wanted to take me out again, and he was going to see some band at the Metro... he was too drunk to remember... and I said, "OK, you can email it to me tomorrow" and got the HELL out of there. When I was a block away, I started to laugh and couldn't stop until I started calling my friends.

hench / February 15, 2006 3:20 PM

not as bad as many of these but still pretty rough...

back in high school, this girl liked me. a lot. she would stare at me during classes & such. she started asking me out on dates for big ticket items (queensryche concerts & such)... i always had legitimate reasons why i couldn't go. one day i didn't, so i ended up going with her to some school dance thing at a holiday inn. we sat in the lobby for three hours looking at the potted plants as both of us were painfully shy & didn't want to dance. her mom showed up to pick her up from the dance about 20 minutes early. so now the three us were sitting and looking at potted plants, not really talking or interacting...

uncomfortable. looking back, she was quite smart & fairly attractive (& willing to buy queensryche tickets!) & i regret being so wallflower-y.

Carrie / February 15, 2006 3:31 PM

My worst was with someone who used to come into my job; it was just an awkward night. He invited me to a concert one week and then invited me on a date the next week to make sure we'd get along well enough for the concert. Fine and dandy, whatever.

In a nutshell: he was 30 minutes late to pick me up and seemed slightly scared or upset that I was towering over him by 4 inches. Guess flats would have been a better shoe choice. He took me to his apartment after dinner so he could go to the bathroom and this is what I saw- he was 30, living in a studio apartment in the Gold Coast and the only furnishings he had were a mattress on the floor, directly in front of the TV and twin size futon that was pretty much in the corner. His video collection included the WWF 1977-1997 box set. He invited me to stay and watch a movie. Yay, oh goody! Do I get to sit on the icky mattress or on the futon that's no where near the tv?? I declined, he offered to go for drinks, I reminded him I was 19, he seemed shocked that I didn't have a fake ID and then he finally took me home. He made sure to mention at least 2 more times how he couldn't believe I didn't have a fake.

The next week I told him I forgot that I had to babysit the night of the concert and couldn't go. That was pretty much the last I saw of him. I should have known better, too- in my head, no normal 30 year-old should date or try to date a 19 year-old.

I also had one date who said "oh yeah I love Thai food. Well, I've never had it but I know it's just like Chinese food." This was the same guy who left his wallet in the car and seemed surprised when I let people go in front of me to get their tickets while he took his sweet time going back to the car to get his wallet. Woops, didn't realize that him leaving his wallet was a hint for me to pay.

anon / February 15, 2006 3:33 PM

I took a girlfriend to Summerdance and I gave up dancing in the middle of it because I was so self-conscious and could not nail the steps down. She took it personally, criticized me, and I felt inadequate and weird. I realized later that I felt this way a lot around her, even when I wasn't being a self-conscious dork.

I've been on dates with people I had little to nothing in common with, but luckily they were nice and normal, so the dates weren't bad experiences.

I have a "first date" with someone tomorrow and she is lovely... hopefully I will not be writing a follow-up.

Ramsin / February 15, 2006 4:02 PM

I have never been on a bad date, because I'm extraordinarily charming and clever, and romantic to boot. In point of fact, I pity anybody who hasn't been on a date with me. Poor you.

johnny-d / February 15, 2006 4:04 PM

Here I was, on what I thought was the best date in my entire life. Dressed in my pinstripe suit and straw hat, off to the Biograph to see a Clark Gable film with not just one, but TWO girlfriends, whoop tee-doo. So we're on the way out of the theater, I'm picturing the fun I'm going to have back at the hideout in three shakes of a lamb's tail with my regular moll and this new Romanian dame in the red dress, and this goddamn FBI man walks up and shoots me dead, just like that. No wonder I had that embarassing lump, making a tent out of the morgue sheet, in THAT location.

hey boys i'm single / February 15, 2006 4:14 PM

Which one do you want?

The one where the dude ran a knife up and down his arm, then later decided to show me all of his piercings and tattoos...which led to him taking out his penis and showing me those ones?

The one where I went to the bathroom to plot my escape from a very bad first date and returned to find him undressed from the waist down only and standing at full attention in my honor?

The one where I got roped into a date I didn't realize was a date and was subjected to a very, very drunk guy and a Shakespeare play...with the former's voice interrupting the latter?

The one where I got flat out stood up, and then the guy called to yell at me for standing him up...although there was NOBODY ELSE in the place we were to meet when we were to meet?

Really, where should I begin?

Loadzone / February 15, 2006 4:17 PM

I suck at dates.

- there was that one homecoming dance during senior year in HS when I showed up with my date and my ex- ran to the bathroom bawling as soon as she saw us...but her date should actually take credit for having the bad date. I just showed up.

- there was that time I offered to walk my broken legged date home from the bar and on the way to her place I could have sworn she was muttering swears under her breath about the way I offered to accompany her home. Luckily we were only a block or two away at this point. I probably shouldn't have grown a moustache between dates.

- then there was the lunch date who told me she had plans to meet somebody after work that day to discuss financial arrangements with a guy she found on Craigslist who offered to pay off her debt No Strings Attached. I thought the chain smoking during the entire lunch was bad enough.

susan / February 15, 2006 4:17 PM

I met this guy through a friend, figured he was a poor hipster/musician/artist like the rest of my friends. He picks me up to go out to dinner. "How about (type of food)? I know a great place!" Sounds good to me. We arrive at a four star restaurant. I am wearing jeans.

He pays for the entire dinner. I am feeling uncomforable about that, and insist on paying half. I pay half. ($70 I can't afford.) We go to a bar. He proceeds to comment on my hair, and asked why I wear it the way I do, and that it needs to be dyed because my roots show. I object and tell him he's an ass, but he says that he "works with models all day and notices these things." Ick.

anon / February 15, 2006 4:26 PM

Third date. I realize pretty quickly the guy is pretty coked up or something. We're at a bar talking, and he starts yelling at me that if I don't go and fufill my unrealized lesbian tendencies ASAP that I'm never going to have a healthy relationship. I was like, "Oookay. I'm going to leave now..." He continued yelling at me as I walked out.

this is fun / February 15, 2006 4:50 PM

I find this funny now, but did not at the time. I was a sophmore in HS and most of my friends were going to the prom with their boyfriends who were juniors or seniors. I wanted to go to the prom too, and my best friend knew of a senior guy who liked me, so she set us up. I was not attracted to this guy in anyway, but stupid me, I wanted to go to prom. We went on a double date with my friend and her boyfriend where we went to Burger King and saw Falling Down. After the movie, we went back to my friend's house to watch TV. Around midnight we all went home. No hooking up occured, but that didn't keep my date from telling all of his friends in the senior class (we lived in a small town so word spread fast) that he had sex with me on my friend's kitchen table - a kitchen table that happened to be located in front of a large bay window that faced a main road in our town. I didn't go to the prom and for the rest of my HS career I was known as the girl who "had sex on a kitchen table on a first date."

More recently, I answered a guy's ad on craigslist. He spent the entire time complaining about how he hated his job, family, friends, coworkers, apartment, neighborhood, etc., all while spitting so excessively while he spoke that he needed four heavy-duty napkins to wipe himself down. This was just one in a string of bad dates I've had at the Belmont Ann Sathers (the guys always suggested that as the place to meet), which is why I won't go there anymore -- I'm afraid it's going to be awful.

Steve / February 15, 2006 5:02 PM

A version of this date o' mine ran on the divine Ms. Zulkey's site a few years back, but it always bears repeating, if only to remind myself why I'm happy to be married now....

A few years back after a bad breakup I was doing some mad furious blind dating via an ad I placed in the Chicago Reader.

Among the responses I received was one from a woman who didnt want to talk on the phone instead, shed send me long emails. (She was also addicted to text-messaging, which I wasn't hep to back in '02.) She told me she was between jobs after the bust but she was working a bit at a clothing boutique in Wicker Park when she wasnt mastering Simpsons trivia. In short, she seemed like my kind of gal.

So we did a meet-up at The Daily early on a Saturday eve, and she showed up dressed for a long, hard night at Neo or something tight sparkly top, skirt and knee-high boots. (Somewhere under all of that makeup, she may have had a face.)

It seemed obvious from the start that we werent clicking in person, especially since she disappeared twice within the span of a half hour with her phone rampant texting to do, I guess. After finishing her screwdriver, she hit me with Well, I have to work tomorrow, so Im gonna hit the road now.

At 8 pm. On a Saturday night. For a job at one of those little stores that opens at noon on Sundays. When shes dressed for a night out doing blow and dancing to Nitzer Ebb.

I told her not to worry about the check, and she asked what I was going to do for the rest of the eve. "Go home and laugh," I told her. And so I did.

ms flips / February 15, 2006 5:09 PM

In h.s. I had a huge crush on a guy friend of mine, so I asked him to the Sadie Hawkins-type dance we had. He didn't talk to me all night. I couldn' figure out why and was too taken aback and clueless so I didn't ask him why. A few days later I got up the guts to call him on it and he told me that he had started dating one of my best friends a day or two before the dance.


Benjy / February 15, 2006 5:24 PM

I went out once with this girl I'd met online and wasn't really planning to see her again, but then she emailed me all excited about how she'd gotten the job she'd interviewed for the day of our first date (doing filing in a dr's office), and wanted to do something fun to celebrate.

We'd discussed during our first date how we both had wanted to see the baseball exhibit they had at the Field Museum at the time, and she wanted to go see that. Well, I did want to see it so I figured one more date couldn't hurt...

She informs me that she doesn't drive, so I have to pick her up in Skokie (where she lives with her parents still, in her late 20's). So I drive from the city to pick her up. She wants to grab lunch, so I buy lunch. We then drive back into the city to the museum. I pay like $15 for parking. Pay almost $40 for tickets to the museum and the baseball exhibit. While in line to enter the exhibit, she says that she just likes to be friends with guys for a year or so before dating them becuase she had a bad experience with a boy once. !?!?! So if she just wanted to be friends for a year or so, why did she never once offer any money for lunch, parking, tickets, etc.? Wouldn't that make it NOT a date?

She also made lots of really dumb comments and just didn't seem to have anything going for her. I just stopped talking because I couldn't stand hearing her stupid comments anymore. We drove in silence from the museum to Skokie. Yet when I dropped her off, she said she had an amazing time and wanted to get together again... That didn't happen!

amy / February 15, 2006 6:19 PM

I dated this guy from the South side a few times and decided to take the red line to meet him where he was to pick me up at Howard. Well, he wasn't there and I was not familiar with the area. He showed up late with buddies who were all wasted. We were supposed to go to a banquet and on the way there he ran out of gas. Instead of walking up the street to get gas and come back he pushed the car while I steered. Then hit me up for gas money! We get to the banquet and he wanders off to talk to people leaving me on my own knowing nobody. I insisted on driving home while he passed out in the front seat. I got as near to downtown as possible, parked and left him there while I took the train home.

paul / February 15, 2006 6:33 PM

On the first date, she upgrades my suggestion of a pricey restaurant to an exhorbanent one. No problem, I like good food, although it was a bit much for the first date. The conversation went like a job interview, except colder and more one sided. I found out nothing about her, except that she knew how to ask questions.

I figured I failed the interview, so I was surprised when she called me (the next day) asking me out to another expensive place. I told her maybe we could go there the next weekend, but she wanted to go that night. She made some hint about it being closer to her place and that maybe I could stay the night if we had too much wine, nudge nudge. This didn't sound at all like the girl I was with the night before, so I was intrigued enough to try it again.

This time the conversation was more like a meeting with a loan officer. She out and out asked me about my credit rating. I made some joke about it not being so good after I'd get the bill with these two meals on it. She didn't find it funny, and pressed me again, expressing how important it was for her plans and goals.

At that point I planned not to be one of her goals and we ate the rest of our meal in silence.

Neta / February 15, 2006 7:37 PM

It's a toss up between the hockey player who took me to see a sweet little movie called "ET" and then tackled me on the front seat of his car while shoving his tongue down my throat and the pothead whose idea of a date was to hang with a bunch of other people in an alley, drinking beer (we were underage) who insisted I stand behind him and wrap my arms around his waist while he peed on a garage. I've not come across such class since...thank you, God!

Lisa / February 15, 2006 9:11 PM

There are a few to choose from . . . all with the same guy. On one, he drove across several states to visit me, then picked a fight at dinner over something stupid that served as his excuse to leave. I think he just wanted me to beg him to stay, which I was stupid enough to do (he didn't, but called me several times to chat during his drive home).

On our final "date," he left me in the morning to hang out with his female roommate, before returning to take me to lunch. He then picked a fight over something stupid (see the pattern), but this time screamed at me repeatedly instead of just leaving. When I told him I wasn't going to stand for being screamed at that way, he dumped me out of his truck on the bridge behind the Art Institute. Did I mention that it had just started to rain? And instead of heeding my instruction never to contact me again, he called repeatedly and when I told him to stop, blamed "coffee consumption" on his screaming fit.

Yeah, those were bad dates. I'm glad I made it out with a life lesson: to listen to my gut instinct next time.

Brandy / February 15, 2006 11:46 PM

I had the worst date that wasn't even a date. I was at a conference, and met a colleague of a friend. He asked me to lunch, which seemed innocuous enough. After I agree, he starts reading my chest like a teleprompter.

The next day we get lunch. This lunch contained at least ten references to things that have made him cry. Lest we think this man is sensitive, not more than ten minutes in, he says (referring to an ex) -
"When I met her, she was in a halfway house. She's messed up. She tried to kill me...But you know how men are - once a woman goes down on you, you're stuck."

Riiiiight. That is how I've snagged my men.

He completely paints a picture of how lonely and desperate he is. And anything we do have in common, I can see the calculations in his head thinking, "I could fall in love with her."

Oh and lest we forget the moment he mentions he's on morphine. I say, "Really?" Instaneously he produced a handful of meds from his pocket.


mike / February 16, 2006 1:35 AM

Worst date ever was with a long term girlfiend. It was New Years Eve 1999 and 30 seconds before the countdown, by the lake in Chicago, she says she wants to go home and starts to take off towards the EL. When 2000 exploded, I was in the middle of a fight, one that lasted well into the morning, ending in one of many breakups.

slb / February 16, 2006 8:51 AM

i've been in a relationship for 10 years, and thus not dating, so it surprises me to see that from a lot of these, girls expect guys to pay for dinner and drinks and etc. is that really how it still works? guys get stuck with a huge tab for a dinner they didn't enjoy because the date sucked? that really seems quite unfair. i guess i just figured people split everything these days. color me naive.

anon / February 16, 2006 9:10 AM

I always just assume that if I ask a girl out I am on the hook for the check. It's not a big deal. I would never ask a girl to an expensive restaurant for the first few dates because, not only is it weird, but it adds pressure that shouldn't be there. I appreciate it if the girl tries to split it, but I'll usually say something like, "oh, I've got it ... I asked you out." If she still prefers to split it, I'm more than happy too. To me it's like opening the door for her - - it's old-fashioned and gentlemanly, etc., and every girl I've dated has always paid for other meals or shows or drinks later, so all the money nonsense balances out in the end.

This has never happened, but if I dated a girl who expected me to buy everything, it wouldn't last very long.

anon / February 16, 2006 9:30 AM

he showed up in a t-shirt that said "slut." he suggested we go to the lincoln park zoo--it's free, you know. then he announced he was having a "party" at his apartment that night, and asked if i wanted to come. i said ok--stupid, but i was a teenager. so his party consists of him talking on the phone to his friend who is at work at a gas station, and later on, one friend comes over. then he falls asleep for like 2 hours. i don't really know what to do, so i just sit there watching tv. eventually, i wake him up to say i'm going home (thank god i had my own car there). without comment, he starts making out with me. ok...i'm willing to do that as a goodnight sort of thing, but i really had to head was like 3AM. he starts groping me and aggressively asking me to stay the night. what??? i tell him i can't, and he angrily snaps, "well then GET OUT OF HERE." uh...right. to top it all off i got a fucking ticket on the way home. i was so disoriented by what had just happened, that i drove right through a red light.

AMF / February 16, 2006 9:30 AM

I went out with this guy for about a month, and had with him what I thought was my worst date, only to be topped a couple of weeks later by something even worse. In retrospect I wish that I would have just ended it after the first "worst" date.

Worst Date Part 1: We are supposed to be going to dinner when we pass by a car dealership on the way. He spots a car that he likes and asks if we can just stop in to check it out. I figure that I like the guy so why not. Flash forward about 2 hours later and we're still at the dealership and he's buying the car. A car buying experience does not bring out the best in people so I got a glimpse into some of the worst parts of his personality - he was acting like a jerk to the salesman, driving like a maniac during the test drives (equating the streets of Chicago with a NASCAR track) and then telling me when it was over that he was too tired to go to dinner so basically I sat around all night like an idiot eating Cheetos out of the vending machine.

Worst Date Part 2: About two weeks later we're driving to a party in his new car. There is just no parking anywhere and after 20 minutes of driving in circles he is getting seriously pissed. Unfortunately, we started arguing about his temper, he started driving fast and didn't realize we were coming up on a red light until he hit the car stopped at the light in front of us at full speed. Thankfully my injuries were not severe (though I was laid up for a couple of weeks) but I am happy to say he completely totalled the car and that was the end of it.

rob / February 16, 2006 10:45 AM

I'm sure everyone has had this experience at least once, but any date where you go into the date thinking you're going to have a very pleasent, fun, enjoyable time with your significant other, but instead get surprised with a "we need to talk" and then an outright dumping, which of course happens in a public space, even though you've already had several discussions about how being dumped in a public space is mean and cruel and humiliating.

waleeta / February 16, 2006 10:47 AM

No bad dates. But that's likely because I never go out on any. Too nerdly.

But what's all this about "splitting" the check???

anon / February 16, 2006 10:57 AM

It was with the crocodile hunter. It was my birthday actually. I had just moved to Chicago and knew only a handful of people at the time, they all happened to be working and as Im not big on birthdays in general I was planning to spend the evening situating things around my apartment. Then I got a call from a guy Id met at a party the previous week, who insisted I not spend the evening of my birthday puttering around my apartment and offered to show me around the neighborhood (he lived sort-of nearby). He seemed nice enough and if nothing else Id be expanding the universe of people I know in Chicago, so why not.

We arranged to meet at a coffee shop, but when I got there I found him waiting outside; he said it was too hot for coffee right now (it was early August) and also that he was feeling full besides. I casually asked him what he had for dinner and he promptly responded two alligator steaks. Uh huh I sort of blinked and after a beat he added with Heintz 57 sauce presumably to not make it seem so weird. Still I found it sort of interesting and after deciding to take a stroll around the area we discussed the various game animals hed eaten (he also claimed to have eaten sloth and hummingbird meat among others.)

It was starting to get dark and we were walking through a quiet residential area when we heard some shuffling in an alleyway, he immediately went to check it out and out from behind a trash can bounded a big, bushy raccoon RIGHT AT ME. I gave a squeal and tried to dodge out of the way but the next thing I knew my date was running straight at me! I jumped again and he bellowed COME ON!! and motioned me to follow him as he chased after the raccoon, down the alley. I was shaken and didnt know what to do so I followed, we ran all the way down the alley and out into the street where SCREEETCH!! A van stopped and there was shouting. When I caught up I found my date already engaged in an argument with the driver, who had apparently hit the raccoon (it was lying under the van.) I looked on as the guy stood on the runner-board to yell into the drivers window and the van took off down the street! My date hung on and beat on the window (which the driver had rolled up) but jumped off as the van turned at the end of the block.

At this point I was pretty speechless but I was in for a bigger shock as my date limped back (he tumbled after jumping off the van) with TEARS streaming down his face. He gave me a long, sad look and then kneeled down and began gathering up the raccoon which was very dead and bleeding. We have to bury him he said. I just stared at him but he was already walking away, so I followed. Id come this far I figured and besides I was a little foggy on how to get home. So we go a block or two until he finds a grassy side-yard that isnt fenced in, he looked around and set down the raccoon and starts digging with his hands, not really paying attention to me anymore. I let him dig for a while and smoked a cigarette. But then a light came on in front of the house and someone started yelling HEY YOU KIDS GET OUTTA MY YARD BEFORE I CALL THE COPS etc. I swear, before I turned around my date was already halfway down the block, again carrying the raccoon.

So instead we went to this park where I smoke another cigarette while he digs another hole. I didnt time it but I think it was about 45 minutes before he finished. He was crying the whole time also and would periodically look up at me and mumble how it was all his fault. I said a couple things about how I needed to be getting back but he was oblivious, I just decided to wait it out. Finally he finishes, dumps the raccoon in and stands up, hes still crying. I light another cigarette and try not to look at him. Well? he says. I look up. SAY SOMETHING!! hes crying harder now. So I mutter something about God please guide this raccoon to your heavenly bosom etc, he begins to fill in the whole and who should show up then but two police officers.

Having a nice night? Uh We got a call that somebody was digging up my date turns around, at this point covered in dirt and raccoon blood. The cops look at him. Sir were going to have to ask you to come with us. And this is the point where my valiant date took off running across the park. He didnt get that far, he tried to leap over a waterfountain and caught his foot and went down pretty hard with the cop right on top of him. They handcuffed him and shoved him into the back of the car, he was still sniffling. I felt kind of bad for him but it was way too much at this point. The cops were nice enough to give me a ride to my street before hauling the crocodile hunter in. We didnt speak during the ride.

The worst part about this whole story was that nobody believed me until a couple weeks later when my date mentioned something about it to one of my friends.

jen / February 16, 2006 11:53 AM

i *really* really hope some of these awful dates are reading about themselves in these posts... hehe.

Leelah / February 16, 2006 12:01 PM

Anon at 10:57 wins!

lawaiter / February 16, 2006 12:28 PM

Not sure if this is a date or more of an experience. While in law school, I dated a girl from California who was attending Northwestern. I flew out to LA during her spring break, and after a weekend we drove up to Oakland when I met her mom.

The week ended with us driving her new-to-her car back to Evanston, with the trip getting more and more uncomfortable the farther east we got. Finally, in Iowa, she ends the relationship. Of course, we still had to drive across Illinois in near-total silence.

anon / February 16, 2006 1:05 PM

I had met a girl through work right after I had moved to Chicago. It was nice enough knowing someone else in the city, we liked the same music and had similar interests. We went out to a bar and to a show for the first couple dates, even hung out with my brother and his then-gf for a double-date pizza+movie night. She asks me to her friend's wedding the following weekend, so we drove to Ohio where I was consistently ignored around people I don't know at all. Apparently she wasn't even really good friends with the bride, who was a fundamentalist Christian and had a dry reception. Later, she told me that I made good arm-candy. When it was time to leave we discovered that her keys were locked in her car. She made a joke about putting the groom's (apparently renowned) skills to work, but ended up instead waiting 3hrs for the AAA lock-picker to show up. We drove silently back to Chicago -- having run out of things to say shortly before the arm-candy comment -- splitting a quiet dinner at Denny's. When she dropped me off I shook her hand and didn't even look back. The next morning I deleted her phone number from my cell phone, which worked out wonderfully because she never called me back either.

granny / February 16, 2006 2:18 PM

back at my alma mater, good old ISU, there were weekly movies played in one of the lecture halls. The movie Breakfast Club was playing, and I agreed to go out with this guy who was pleasant enough, but a bit of a nerd. So before we went to the movies we had a few beers and during the movie I heard him burp, and then he threw up into his sweater.

Poor Bill. I'm sure he's a wealthy, successful computer dude now, and has lost his nerd status, but I couldn't look at him after that.

granny (go redbirds!)

april / February 16, 2006 2:25 PM

A friend set us up. We had emailed back and forth for about a week prior and he was a *great* writer, which is hot, so I agreed to meet up. We went out for dinner, but the guy was overly hipsterish [living in the suburbs, mind you, WITH HIS PARENTS] and was hell-bent on being rude to people. To the waitstaff, this slightly porky girl on the street, the door dude at a show, EVERYONE.

His idea of 'funny' was to be sarcastic/malicious and pointing out random stranger's faults in a passive-aggressive manner. He'd say shitty things within earshot. I was so embarrassed to be associated with some jackass who obviously has his own esteem issues.

That was 2 1/2 years ago and he STILL emails me [all unanswered].

From what I hear, he still lives with his parents. Who else could live with him?

Here we go again... / February 16, 2006 2:33 PM

My worst date was several years ago. I had just moved to Chicago and didn't know anyone. My older sister came to town with a group of her friends, and I met up with them for a chance to finally check out the nightlife. The concierge at her hotel told her that Rush and Division was "where it's at," and I didn't know any better, so off we went. I ended up meeting a cute, funny guy that my sister and her friends all drooled over. We exchanged numbers. Two weeks later I hadn't heard from him, so I called him and left a message. He called me back at 10 PM the following Friday, asking me to come to his place and watch a movie. I was so thrilled to hear from him that I said yes, but I reconsidered on the way over. As he got in my car I asked "Would you mind if we went out to a movie? Or got a drink somewhere? We don't really know each other, and I guess I'd feel more comfortable going out than hanging out at your place." He was ticked and replied "If I'd known you were gonna pull this, I wouldn't have just thrown on this T-shirt. I'm not exactly dressed to go anywhere. But, FINE." Oooohkay. So we ended up at a bar around the corner. I came back from a trip to the main bar to find a girl sitting on my stool talking to my date, my coat in a puddle of beer on the floor. He claimed she had hurt her foot and just needed to sit down for a second, but she clearly didn't know he was with someone and apologized as she got up and left. Hmmmm. The conversation was awkward, and he managed to bring up his ex-girlfriend repeatedly, but he made a point of taking my hand and saying "I would NOT be here with you if she were at all still in the picture." Shortly thereafter, he said he wanted to call it a night. I drove him home. He asked if I would like to see his apt. I love to see where people live, and I did want to use his restroom, so I said, "Ok, but only for a minute." He gave me the tour of his huge apt, making sure to point out that many of the furnishings belonged to his ex. "That shower curtain with the ducks was hers. I just haven't gotten a new one yet." Then he pointed out that the bathroom was right next to the living room, so "I'll be able to hear everything." When I emerged from the bathroom, he handed me a fresh beer and insisted I sit and listen while he played Dave Matthews Band tunes on his guitar. I kept my coat on and sat patiently through his rendition of "Crash Into Me", then I said I really had to be going. He said he'd walk me to my car, but he had to "take a leak" first. While he was in the bathroom, his phone rang and the machine picked up. A screeching harpy was on the other end, yelling "It's me! I know you're probably f4#%6 some b&@^%# right now, but you could at least pick up the %^$*& phone! Are you there?! PICK UP!" He raced out of the bathroom and grabbed the phone. While he was talking to her, I waved goodbye and started down the steps. He ran after me, still talking on his cordless phone, insisting I let him walk me to my car, parked about two blocks away. The whole way he continued to talk to her, but either lost his connection or hung up with her when we reached my car. I drove him back to his place and said "I hope you can work it out with her." He insisted that the phone call was from his sister, who was just drunk, and that he really wanted to see me again. I said "I don't think so." and drove away, leaving him on the sidewalk with a ringing phone in his hand.

Anonymouse / February 16, 2006 3:37 PM

I was back in Chicago and finally ready to date again. Brian was a drummer for another band that was playing at the same open mic as my band. I should have known when he first asked if I was a Latina and then asked if I had a fiery temper. I should have known when he invited me out to see The Wailers and kept asking, "Are you sure you can handle this?"

We met up at a Lincoln Park bar across the street from the Park West. At first, it was just a boring little date where you realize there is absolutely no spark between you and the guy, but we were then joined by his friend. He invited his friend along on the date - Some 40-something guy who kept referring to his kids and to a vacation he took in the Keys back in the 70's.

We were watching the show, and I decided to just stay put for the rest of the evening and drink my Jack &-Coke's (which I kept covered with my full palm). As I was watching the show, I smelled that someone in the area had broken out the pot (not really surprising) until I turned around, and there was my date, smoking and offering me a hit.
I don't mind a little weed, but not on the first date, man!

He got so high that he spent the night dancing by himself and drinking. His friend, though, stayed at our table, so he could try to play footsie with me.

When Brian tried to compliment me by telling why he talked to me at the open mic, he said, "You had that natural look, you know, like you looked natural, and you had the whole package!" (He said "whole package" as he cupped his hands to outline the shape of my body).

He offered me a ride home, even though he was so wasted, he could barely walk straight. I took the bus.

MikeH / February 16, 2006 4:12 PM


The more of these I read (my own included), I think that we, as a gender, would probably fare much better if we just laid off the booze (and apparently in some cases, weed) altogether on first dates...

baldeesh / February 16, 2006 4:20 PM

I concur with MikeH -

One time I went out, had too much to drink, and brought a guy home.
He wouldn't leave the next morning/afternoon, and after that desperately tried to turn a one-night stand into a relationship.

So, no booze (for me) at all for the first few dates.

Baldeesh / February 16, 2006 4:21 PM

No booze on first few dates or around people I haven't known for very long.

LeahW / February 16, 2006 4:30 PM

It was a spur-of-the-moment, impulse Sunday second date.

We went to a cemetary.

He showed me his future burial site.

To be fair, it was a really nice cemetary.

Nick / February 16, 2006 5:39 PM

I met someone online and we decided to go to a White Sox game for our first date during Labor Day weekend. During the 6th inning she gets up to go to the bathroom and never returns. I get a text message from her about an inning later saying that she had some "female trouble" and had blood all over her white pants and that she took a taxi home because she was embarrassed.

I never heard from her again after that night and to this day I wonder if she ditched me and made up an excuse or if she was telling me the truth. Either way, the date sucked balls after that happened and I didn't even bother staying for the fireworks.

The only thing that made me feel better last year about that date is that she was from NH and was a Red Sox fan and I got to go see the White Sox destroy the Red Sox in the playoffs.

Rebecca / February 16, 2006 6:51 PM

It's a tie between:

A boy who asked me out in high school and picked me up to go to the movies in a monster truck with a big confederate flag on the back...

And a third or fourth date with this hot, smart girl. We went back to my place after a nice dinner were talking on the sofa. Things were looking promising: great chemistry, lots of heavy flirting and then it kind of tapered off. I couldn't figure out why. She left, I was disapointed and sat down on the sofa, where she had sat, to ponder what I might have said/done wrong. And then I saw, in what would have been directly in her line of sight, a condom wrapper on the otherwise immaculate floor. Nothing kills girl-lovin' like evidence a guy was there first. I kicked myself for a week after that.

Carlotta / February 16, 2006 9:16 PM

Whew, I haven't been mentioned in one of these (yet).

Steve / February 17, 2006 9:42 AM

Carlotta -- it's probably the non-disclosure agreements that you require your dates to sign in advance....

Here Comes Handsome Johnny / February 17, 2006 9:57 AM

I've been holding out on this, trying to decide which of three dates was the worst.

About four years ago, I did my first bout of online dating, putting up an ad for about three weeks. On the first day I got flooded with responses from women (I'm male, now mid-30s), but one stood out; flirty, flattering, very attentive to the details of what I'd written. I replied; she turned out to be a UIC prof three years older than me. The exchanges got sexy and tense in a good way, and finally one weekday afternoon she asked me to come straight to her place after work, so I did.

She fixed us drinks and never stopped staring and smiling as we sat and chatted, and before long I leaned in to kiss her. She grabbed me and started growling about how she'd been waiting for me for so long, she wants me so bad, etc. She took my hand and led me to the bedroom. I'm thinking, Online dating is great! I'm set for life, man! So the deed was done extensively, and I was too glazed over with lust to really notice the weird things she started saying and doing (I'll spare you the psycho-Penthouse-Forum details of those).

But when it was over and we were collapsed and afterglowing (me on the bottom), the adoration on her face suddenly changed to a sort of disgruntled fear. I watched the transformation; it was amazing how it came out of nowhere while she stared into space, and then swiftly focused on me.

"Why did this happen, ****?" she demands of me. "I've always been the faithful one." Huh? I reply. Then she informs me of her live-in boyfriend (!!) of five years' standing (!!!) who happens to be away for a week (?!?!) and who has never said he loves her, and why the fuck hasn't he? What the fuck was wrong with men? Huh? Wha? I reply knowingly. Long long pause.

"You don't cross country ski, right?" she suddenly continues, as though this is a natural progression. Um, no, I admit. "WHY NOT?" Because...I don't want to? She doesn't like that answer. Long long pause. Her stare turns really angry. "Are you a LEO?"

Are you kidding? I say. Astrology? "Answer my fucking question, are you a Leo?" I don't answer; I'm trying to remember how I got here. Long long pause. She tosses her hair haughtily and says, "Well, I don't lie around doing nothing in the evenings. You have to go." I go.

She's contacted me a few times since then, first to say that her boyfriend dumped her on September 11th and did I want to meet for dinner? and most recently to propose that I come help her fix up her new house. Each time, she has completely forgotten the details of our one "date," except for the sexual ones.

Chris / February 17, 2006 10:14 AM

This is the best thread ever. I never even imagined dates could be this bad.

I'm glad I've never been on one that was so bad it was worth mentioning here.

spence / February 17, 2006 10:26 AM

This isn't a bad date I've been on, but one I've witnessed:

My girlfriend and I went ice skating at Millenium Park a month ago and there was long line to rent skates. In front of us, there was a couple who were obviously on their first date. The guy literally talked for an hour straight while standing in line. Every once-in-a-while he would ask her something like "What do you do again?" and "What kind of music do you like?" and as soon as she would start to answer he would cut her off and go on about himself. My girlfriend and I could tell that this girl was more than annoyed. After we got on the ice, I saw the girl falling about every 3 seconds with this absolutely miserable look on her face. I learned a valuable lesson after that, even though it seems romantic, never take a girl ice skating on a first date.

Jason / February 17, 2006 10:30 AM

My worst date was a few years ago near the beginning of attending college. I knew this one girl in my dorm and her roommate was into me. So I was going to go out with her. She calls me one Friday night and asks if I'm busy, and so I think, what the hell, and say "Sure, want to go play some pool?" The response was, "Oh, sure...I'm not that good at pool, but I'm up for anything."

Uhhh, okay. So I meet up with her and walk over to the union to get a table. We start playing, and during the game, she starts getting friendly.

"I walked by your room the other day and you didn't have a shirt on." (I used to sit around in my room shirtless.)
"Uh huh..."
"Yeah, I wanted to shout 'Wooo, sexy!', but I didn't."
"Hehehe...yeah, well that's not true though."
"Oh, I beg to differ."

She then proceeded to smack my ass a few times while I was playing pool, and eventually we left and went back to my dorm, at about 10pm. I turned on the TV and we sat down on the futon, purposely at opposite ends since I was already freaked out a bit. In about 10 seconds she had just scooted over and entirely closed the gap between us, and then gave me a huge bear hug (this girl was also taller than me and I'm 6'0", and also a bit bigger). I'm sitting there staring at the screen, and she goes "You want a massage?" Not knowing what to do, I say yes, and she starts rubbing me all over my chest and back and stuff. I was thinking, "Crap...she's going to try and make out with me any second now." We're sitting back on the futon and she's just staring at me, and all of a sudden, my roommate walks in. "HEY, BUDDY!" I yelled, and got up and started screwing around with him. I was never so happy to see my roommate in my entire life, hahaha. Finally a while later she left and said "So, call me this weekend?" "Yeah, sure..." Never again did we speak.

anon / February 17, 2006 10:50 AM

I find this whole thread to be really fascinating. I love how for some people, a really bad date involves a harrowing, terrible experience, while for others, a really bad date is simply because they didn't get laid. It's a rather telling characteristic, frankly.

Spencer / February 17, 2006 11:01 AM

Posting anonymously is also a rather telling characteristic, frankly.

Here we go yet AGAIN / February 17, 2006 11:03 AM

Not sure if this qualifies as a "date", but it was certainly awful, so here it is...One weeknight my friend and I put on our red sweaters and jeans and went to cheer on the Red Wings at the Gin Mill. We each struck up conversations with guys during the game, and afterward my new acquaintance, "Chad", who was in town for a week apt-hunting, bought us all a round of drinks. Then he suggested the four of us go to an Irish pub he liked for more drinks. Chad made quite a show of insisting on paying for everything--cab fare, cover charges, etc. Ah, so generous of him! Nice guy! My friend had driven to the Gin Mill and made a point of telling him that if we were all taking a cab to this pub, she wanted him to pay for our cab fare back to her car, or she wasn't interested in going. "No problem!" he insisted, and off we all went. After our first drink at the pub, Chad began insisting that I leave with him and go across the street to a tequila bar. I said I preferred to stay with my friend, and the guy she'd met, "Steve". He kept whining at me to go somewhere where we could be alone. He said he thought I could really be "my true self" if my friend wasn't around. This from some guy I'd known for 2 hours? I was liking him less as the night wore on, so I was not up for that, and refused from then on to let him buy me another drink. He ordered one for me anyway and it sat untouched, while he chided me that I didn't seem drunk at all. At one point as I sat next to him at a table with my leg crossed in his direction, he reached down and pulled off my shoe, telling me "I'm glad you have your toes painted. That says a lot about you." Eh. I grabbed my shoe back and scanned the room for my friend and Steve, but they were standing at the bar with their backs to me. Then, putting aside any pretense of being a decent, genial fellow, Chad began to bargain with me for sex. He slurred "Come OOOON. How much money is it gonna take to get you back in my hotel room?" and waved a wad of bills drunkenly in my face. I asked "Did you think I was a hooker this whole time? Is THAT what your problem is?" He backtracked, saying he just liked me and wanted to "make the most of our time together." I told him it wasn't happening, and that he was working my very last nerve. He stood up, shouted "If you don't wanna f-- me, then f-- YOU!" and stormed out of the bar.

ben / February 17, 2006 12:01 PM

I was hanging out with a girl whom I knew from a while back. It was nice catching up and I felt comfortable around her.

We met some friends out for dinner one night. Then we headed to a bar to hang out for a while. I notice that as the night goes on, she's less and less interested in what I have to say, and she's hardly talking at all anyways.

She ends up hanging out with my room mate and his buddies - so I play it cool and hang out with some other friends who show up. It's getting late and I've already written her off - she finally comes back over to catch up.

Me: "Hey, I thought we clicked and now it's as if you changed your mind.. and that's ok. But I like you. Umm, what's the deal? Because I'm not feeling it now."

Her: "...[cricket sounds]..."

Me: "So you're taking off?"

Her: "...[more crickets]..."

Me: "I'm going to stay here then. I'll see you around."

Her: "...[said crickets]..."

Later I find out that she has a thing for my room mate. And that's ok - just wish she could have been [just a little bit] more upfront with me. She flaked on him a few weeks later. Go figure. What a train wreck.

dan / February 17, 2006 12:19 PM

I've had a few bad dates, but this was hands-down the worst. I met a girl a few years ago at a show, and we went on a couple of nice, relatively low-key dates. She tells me that we should go see "Tsar", this band that she had seen open for Duran Duran. Coincidentally enough, Tsar was coming around again and opening for my friend's band at the Metro. So we figured it'd be a perfect show to go to.

We get to the Metro and see a bit of Tsar, and they're okay. The girl then proceeds to get pretty drunk over a couple of MGDs. Tsar's set ends, and the next band starts setting up. At this point, I notice my friend in the crowd, and ask my date if she wants to go say "hi" and meet him.

She tells me "Not really. Go talk to him yourself."

I'm a little unnerved by this, but I say "ok", ask her if she needs anything, and go talk to my friend. As I'm talking to him, I notice that the singer from Tsar is standing behind me. I ask him if he wouldn't mind meeting my date, as she really likes his band. He's really nice and agrees.

We both over to my date, who at this point, looks a little blitzed. I introduce the singer to my date, who then proceeds to ask him a bunch of questions about Duran Duran. The singer's really nice about it, and starts telling a story about Simon LeBon. My date interrupts his story a couple times, saying she's not interested (she prefers their bassist), and then cutting him off by saying "I don't care about your stupid story. Simon LeBon is a douchebag. Tell me a story about John Taylor!"

The Tsar singer says that he's never met him (I guess Mr. Taylor's not in Duran Duran anymore. I'm, at this point, learning more about Duran Duran than I ever wanted to know.) My date, who is now visibly drunk, starts berating the singer. "How can you not know him?! I don't understand! He does music and lives in L.A.! So do you!" The Tsar singer gets miffed and walks away. My date says something about his hair looking "queer" and turns to me.

The awkwardness is pretty palpable at this point, so I suggest we get close to the stage to see my friend's band. They come onstage and play a couple songs. My friend is introducing a new song she wrote, when my date yells, "Shut the fuck up and play!" My date then turns to my and smiles, saying "I hate it when bands talk between song. Shut the fuck up, y'know! This is a show, not your fucking therapy session!" Evidently, this was supposed to be a joke.

I look at her like she just kicked my dog.

My date realizes she made a bad move and apologizes, saying she's gonna go get me a beer. She's gone for a half-hour, and I decide to go look for her. I find her next to the bar, with two beers in her hand, chatting with the singer from Tsar. She sees me and loks frightened. She runs over to me and says "Sorry, he just cornered me!"

I say that it's no big thing, and we watch my friend play for another couple songs. My date then excuses herself to go to the bathroom and doesn't return. My friend's band gets offstage, and I start looking around for my date. I leave the Metro after 20 minutes of looking, and find her in the Raw Bar next door, hanging out with Tsar.

"Oh my God!" she says, "Is the concert over?"

I nod "yes" and she tells me to pull up a chair. She wants me to meet the band! So I tell her, "Look, this isn't gonna work out."

She gets really sad and hugs me. She tells me she's hugging me "heart on top of heart, like my Mom used to" whatever that means.

I proceed to go out that night with my friend, and we get good and drunk, swapping bad date stories.

p / February 17, 2006 1:29 PM

wow. Ill wager alot of the people getting slagged here got the worst of these dates. Jason is clearly hoto, and lots of others are simply relishing this whine-fest far too much. Gettin a little craigslisty though. Although the UIC prof one gave me a shudder, as did the iceskating. And redwings attire, worn at the likes of the gin mill invites the advances of those who dig that mode of getup, which you got.

Anonymouseeeee / February 17, 2006 1:33 PM

So I just went out on this date to be able to say that I was moving on from my recent break-up and actually dating. Really, it was too soon to be dating again, which must be why I chose Maria Full of Grace, a film about a Colombian drug mule. Not exactly romantic, but to be fair, when Ray picked me up at my place, he was using a tall umbrella as a walking stick, a la Huggy Bear.

Throughout the date, he tried to impress me with the fact that he was 31 and older, more "experienced" (I was 23). The date was average and boring, as he went with over-the-top "get you into bed" compliments and about how much he loves movie production and that he is a 'film-maker'. The deal breaker was really when he couldn't handle his bottle of Coors Light and complained of dizziness, while I was already on my second Guinness. Weak.

When he tried to hold my hand and ask how the date would end, I told him it couldn't go anywhere because I had just ended a relationship and wasn't ready for anyone. That went over well enough, until, on the way to the train, he started yelling, "Yeah, but if I was a complete asshole, I bet you'd be all over me! Right?!"

2 months later, I saw him in an issue of TimeOut NY. I found out he was a pornographer under the alias "Stylz Haaz". The company was called "Elitrious Erotica", (Elitrious being his dead mother's middle name!) that allowed average couples to pay to be the stars of their own pornos.

I really missed the boat on that one!

Don't know that one / February 17, 2006 1:46 PM

p - "hoto"? What's that?

Haha / February 17, 2006 1:53 PM

I think "p" is mad because he's the subject of one of these posts!

Anonymouse / February 17, 2006 2:08 PM

When I was 16, the new boy in my class, Marlos from Brazil, asked me out to a dance at his church. I should have known better, especially on a Sunday night. That night, when I answered the door, a short mustachioed man was at the door, and I told him he had the wrong apartment. Turns out, it was Marlos's little brother, a 14 year old with a mustache, because Marlos was too lazy to come to the door himself.

We got to the church and he leaves me with his mom, sister and grandmother to talk, because his father is the pastor at the church and they were preparing the Mass (wha?!). I had to sit for 30 minutes explaining my classes, my GPA and future plans to comlete strangers.

Then the Mass began. Marlos couldn't sit with me, because the service would be in Portuguese and he had to work as the interpreter. I sat alone, while my date's voice spoke solemnly through my earpiece about Armegeddon and how we are headed to Hell if we don't repent (it was a pre-Christmas mass).

Everyone proceeded to the rec hall to listen to the boombox and play basketball (this was the "dance" part). Marlos asked if I wanted a soda. I asked for a Sprite, and he pointed to the food cart and let me know it cost 50 cents. We hugged and he let me know I'd be driving home with his mom, siblings and grandparents.

anon / February 17, 2006 2:39 PM

leaving aside the blind date that gave me bruises (and not in a hot sexy way)...

College. Friday night. I'm out with some friends at a restaurant and we run into some people my friend knows from church-group (sign #1). This guy chats me up and asks for my number, ok. the time is 1 AM. He calls me less than eight hours later (sign #2), at 8:30 am on Saturday. I'm groggy, he's chatting, we agree that there are no good Italian restaurants in our town, and he offers to take me to one in the adjacent town THAT NIGHT (sign #3). My sleepy self is too out of it to make up plans, and plus he knows my friends, so I say ok. He comes to pick me up and I offer to drive (thinking I shouldn't go off in a car with a stranger). He wants to drive, because he just got his car detailed. Ok. His car turns out to be a shitty volvo with a cracked windshield. (sign #4). We chat on the drive out, and he keeps saying, "I went to the ballet once and I really liked it. But I'm not gay." (signs #5 -10). Did I mention he was ex-military? (sign #11). We drive out to the next town, and I say, 'oh, that's our exit!' He disagrees, he thinks the restaurant is in a different area. I've been there, he hasn't (sign #12) So when we get off at the next stop, I say, 'well it's that way, so you should turn left.' He turns right (sign # good thing I'm not hungry).

To save you the suspense, we do eventually turn around and get to the restaurant, where he chats up the waiter (sign # uh- what?). I go to the bathroom, learn to speak Italian, come back, interrupt to ask a question about the dessert menu, and they're still talking. At this point, I was just hoping that he got the kid's number, because what the hell. So we head back to the college town, where he wants to continue the date over coffee (me, in my head: 'you thought that went well?') but I beg off, citing that tomorrow, after all, was Sunday. (take that!)

He proceeds to call repeatedly, and when I can no longer avoid him, I up and tell him that I'm just not interested. He says, 'well, I commend you for your honesty.' like I deserve a medal. Honesty? You want honesty? You're gay. I don't date gay men. Go find someone who does!!

And once more around the floor... / February 17, 2006 2:53 PM

My myriad bad dates had driven me to join an online dating service, something I swore I'd never do. At first I was cautious, only meeting someone after a week or so of emailing/phone calls. When it became clear that that was no guarantee that I was actually getting to know a prospective date, and, worn out past the point of caring quite so much, I began to meet men in person shortly after our first emails were exchanged. Such was the case with "Luke." I liked his profile and his emails were hilarious, so we exchanged numbers. I could tell on the phone that night that he had a slight stutter, but it didn't matter to me. We made a date for the following night. It started off relatively well at a neighborhood bar--good conversation, although he did feel the need to disclose his doper past, and emphasized "I've done every drug in the book. Twice." We continued on to another bar, and, as it was my turn to buy the drinks, I went to the bar and he went out to the beer garden to try to find us a table. I made two laps around the crowded patio, beers in hand, before I spotted him sitting at a table full of his friends. He finally noticed me standing there and introduced me around, but did not get up until I handed his beer over to him and said "Well, I guess we should find ourselves a table or something. Nice meeting you all." We found a place to stand against a wall, and he began talking about how unattractive he was and his stutter. I said I thought he was just fine and we actually argued about it. Matters were not helped when I went to get us another round of drinks and a nice, cute guy tried to strike up a conversation with me just as Luke returned from the bathroom. I politely told the guy that I was on a date and he left, but Luke asked "Who the hell was that?" Soon the bar closed and he asked what I wanted to do next. It was pretty late and I reminded him that I was helping a friend move in the morning way out in the suburbs, so I wanted to end the date. He snorted "You need to work on your fake responses." I said "You need to work on your first date etiquette." and got out of there.

emily / February 17, 2006 3:08 PM

in highschool this guy asked me out on a date to see a movie. he showed up in a baseball cap and ripped jeans and we all sat in the front seat of his mom's old hooptie because the back seat was filled with junk. his mom shopped at the mall while we watched the movie, we even had to wait for 45 minutes for her to meet us back in the movie theater lobby. we didn't really hit it off, so i told him the next day that i didn't want to date him anymore. he called me constantly for about two weeks afterwards, crying, trying to convince me that we were meant to be. he even made a huge scene at a football game, bawling and crying and sending his friends to talk to me for him.

after reading all of these posts, i'm thankful that i've never really dated as an "adult", having met my husband when i was 19. we've never had a bad date.

Erica / February 17, 2006 3:34 PM

My first boyfriend took me to Chuck E. Cheese after a winter formal because he worked there and could get free food.

Say it ain't so / February 17, 2006 3:51 PM

First of all, Erica, the food may have been free--but it was also great. Second of all, lest you forget, I did spring for that game of ski-ball.

Dirtyguy / February 17, 2006 5:22 PM

I have a total first non-date tomorrow with a girl I really like a lot, and y'all're makin' me way nervous. Stop.

My worst date was one of those high school dances. I don't remember which one. I fuckin' hated those things. No dancing was done by me, that's for damn sure. The girl I was pathetically (seriously) in love with had a boyfriend, but she asked me to take her superhot cousin. Being a complete tool, and wanting to show up with a superhot babe, I agreed.

And her superhot cousin would not shut up about Hanson. The band Hanson. She was like, their stalker or something. It was really weird. I tried to act interested, but come on, Hanson? This was prolly a couple years after Mmm Bop. Nobody liked Hanson. Except her. She kept sayin' how she and their mom are good buddies or something. And she sleeps on their lawn. I don't even remember the stories.

Fuckin' Hanson, man!

And I had to see the first girl kiss her boyfriend a lot. That sucked ass.

hmmmmmm / February 17, 2006 5:27 PM

Dirtyguy...was this in Indiana???

Dirtyguy / February 17, 2006 11:45 PM

Naw, Rockford. Is Hanson from Indiana? I guess then it wouldn't have been so awkward.

girlwithaspirin / February 18, 2006 12:11 PM

Ah, such fond memories of the guy who wanted to plan "a big surprise" for me on our first date. He didn't have a car, so he asked me to pick him up. Fine. Parking was a bear in his 'hood, so I searched for well over a half hour. Then I went inside, already more than a little annoyed. His dirty, cramped apartment was stuffed to the gills with Notre Dame paraphernalia -- right down to the Golden Domer futon that functioned as a couch. (And sported what appeared to be Golden Pee on one side.)

He asked me to sit down. Which I did, on the non-pee portion. And then he proceeded to stare at me, smiling more than small talking. After 20 minutes, he asked if he could join me on the futon. I asked him where, exactly, were we going for the night? At which point, he said, "Nowhere. Surprise!"

No surprise, I got the fuck out.

Anthony / February 18, 2006 1:45 PM

It was THE NIGHT of the day my girlfriend of three years and I broke up.

I ran into this girl I knew from college at the Bungalow -- she had blown me off a few times, so I politely said "Hello" and started speaking to her friend. We got along great: same travels, same music, interestes, etc. She was quite attractive, I was diggin' her. I think the feeling was mutual. We went to another place. Afterward, my buddy and I walk them to her car. I ask for her number, she says: "I can drive you home." Wow. This never happens to me (probably the whole 3 year thing).

We drop my buddy off at his car, and her girlfriend off, and we're on the way to my apartment. I have to urinate WAY BAD. I'm trying to contain it to the best of my ability, but IT HURTS. So we pull up in front of my building. I am trying to make the fastest "I like you a lot -- I definitely want to see you again -- but I gotta go" exit, and she leans into to kiss me. It was awesome, and I love it, but OH!! She asks if I want to come home with her, I say "Hell yeah! But one little thing, I really need to use my restroom." She laughs, I pee, come back outside. We go to her place. My ego is lovin' it, especially after feel sorry for myself all day. We fooled around, but no sex, because I psyche myself out until I feel comfortable.

Perhaps a week later, I meet her for sushi. She looks incredible, seriously, it was the first time I was out with somebody and thought, "I don't believe this girl is out with me." It goes ok, a little less intense, but still decent. We go back to her house, hang out for a bit, start fool around. I know I've already psyched myself out. No sex. We wake up in the morning, and I put my jeans on, and they're WET. Her f-cking pug had lifted his f-cking leg on my jeans!! And I have to go to work! She tries rinse it off, blow dries them, etc. No avail. I ended up leaving work early that day b/c I couldn't take it.

We hung out for maybe three more weeks (I suspect guilt or sympathy at work), had some terrible sex, then she just stopped responding. I don't blame her, in fact, she saved me from getting back together with the girlfriend, and the subsequent life of misery that would have entailed. I was too attached to realize it. I wish I could take her out again now that I'm right in the head.

I guess that's not a bad date story, so sorry, but it's my most interesting.

Sarah O. / February 18, 2006 6:00 PM

Can't decide between two first and last dates.

1. Blues guitarist took me to the symphony. He dressed in a black cape, top hat and vampire fangs. He passed out during the first movement and snored loudly. God only know what he was on.

2. Rich guy took me out to dinner at a very swank restaurant. He passed out, face down into his dinner plate. Found out later he had a problem with prescription painkillers.

theloneson / February 18, 2006 7:53 PM

It's not always the OTHER person who makes the date bad.

In my sophomore year, I went to a party thrown by a couple friends who were seniors. At their apartment, after a few drinks I meet an attractive young woman in the kitchen (of course). We banter in bad high-school French, and she invites me back to her place with her friend and date. (Score one for the skinny guy.) While friend and date wander off to another room in the large house (her folks were out of town for a week), I hang out with my recently acquired date in the basement family room. After a nice make-out session, she invites me to her sorority formal a week or two later. (I'm GDI, but happy to attend a good party.) After chatting with her during the week, I show up @ the hotel suite the night of the formal in suit with a fifth of Absolut, but no mixers. My date, her friend and the other dude are already there. In a clear sign of the lightweight that I was at the time, in my mind, the best choice of mixer is Orange Crush from the hallway vending machine. (Not that I couldn't drive to a nearby convenience store, mind you.) Anyway, I pour wickedly strong cocktails (which taste like nitro-Absolut Nyquil to me), and end up HAMMERED in no time. While the other couple head down to the dance, my date orders room service -- steak -- which I'm too f'ing drunk to even finish. We eventually make it down to the dance, I stumble through one or two songs, and end up sitting next to the den/house mother for at least half an hour trying to sober up. (Doesn't happen.)

At some point well past midnight, the dance is over and my date (she's put up with me this long?!?!) wants to go swimming. In spite of the fact the indoor pool is closed, we take the plunge without getting collared by the hotel staff and make it back to the room. Much to my chagrin, I pass out before any whoopy happens. The next morning, my date and I wake up head our separate ways, never to cross paths again.

After more than a decade of short-term relationships in Chicago, I'm in a multi-year relationship, pondering my future. Perhaps I'm still a bad date. But at least I don't get drunk on the first and second date EVERY time now.

Mel / July 2, 2006 2:21 AM

I had a really bad dat from craigslist I responded to this guy's ad that was really cute,his profile seemed ok. Anyway I drove 45 minutes to his house as I find out later he has no car. Anyway I keep calling him because I can't find the house he seems fustrated because I keep calling him. Iater find out he has a prepaid cellphone. Anyway he decides we will go to this neighborhood bar he knows. We did not pay because he knows the people there. So we played a round of pool but then he leaves me standing near the dance floor around people i did not know. SO I begin to get angry, he come to talk to me so I ask do you drink he says yes if you want to buy me a drink I drink white wine. I get even more angry then he proceeds to ask me if I want to buy him dinner. At that point I had enough I leave the bar but I found he had left his bag in my car. So I call him and tell he to come get his shit. Well he comes out the bar yelling "that is what is wrong with you women you don't know how to treat a man" HUH!!!!!!

dude / December 4, 2008 6:45 PM

She's a drop dead beauty. I was surprised to get a date with her. After the first meeting, I thought she wasn't interested, so I started seeing some one else. She kept pursuing me until I told her I only wanted to be friends.

Months later I end up single again. A mutual friend presses me to ask this girl out again. She was nice and pretty, I didn't think she'd be interested but I gave it a shot. She said yes.

Three dates later and nothing. She asked me to take it slow with her, not rush into anything, and so I've been in it just to get to know her. We went out to a science exhibit last week; the only conversation she could hold was when she'd bring up the weather. She brought it up several times. I asked her questions, made jokes, told her pointless stories about myself just to break the silence -- nadda. She has the personality of a coat hanger, and is about as affectionate as an old time school marm. What a waste of a pretty face. The prettiest girl I've ever dated and I've dodged her twice now.

Alli K / December 4, 2008 7:54 PM

I went on a blind date freshman year of college with a guy that one of my good girlfriends set me up with. He was cute and seemed nice, albeit very nervous. We went out to dinner and then after that went back to his place to chit chat before we went to a party. We met my girlfriends at the house party and he proceeded to get so drunk he couldn't speak properly or walk. We brought him back to his place (one of my girlfriends and I holding him up) and put him to bed. His roommates were out and he was so drunk that I was worried something might happen to him (I hadn't really dealt with many idiotically drunk people before so it was scary) and so I decided to deny the ride my friends offered me in favor of making sure he didn't die. There was no other place to sleep except for his tiny twin bed or the floor, so I snagged a blanket and camped out on the carpet. I woke up about an hour later with massive neck pains so I decided to move onto the bed. Precariously on the edge of the bed, I felt a hand creep up to my stomach and the guy began to fondle me. I told him to quit it but he was so drunk that he couldn't understand me. I finally got him to stop saying ridiculous and vile things and he went to sleep. I didn't sleep for the entire night.

At about six o clock in the morning, as I was staring at the ceiling, I felt something warm and wet on my leg. I proceeded to jump out of the bed to find the guy wetting the bed in his sleep. Mortified, I went to the bathroom and wiped my leg off, went back to the room, and woke him up. I told him to go change and that I wanted to go home. Turns out, he was too drunk to drive still so I drove us back to my dorm room in awkward silence. Still being too drunk to drive, he slept on the couch only to be kicked out at around ten.

Needless to say, I never saw him again.

And, now I can have a good example of someone who is piss drunk.

noelle / December 4, 2008 10:15 PM

dang. i dont have any as bad as some of these. haha, this one date though, if you can even call it a "date": breakfast for dinner at waffle house (he did pay though) and then a walk on the beach. at night... in january- COLD. he offered me his jacket, but i could tell it was a big imposition for him. put off by his obvious annoyance, i declined and shivered uncontrollably instead. after a little conversation, we sat on a picnic table watching the surf & he suggested that since it was so cold i should probably cuddle up to him, when he proceeded to ram his tongue down my throat over & over. needless to say, the long walk back to the car covered in sand was an uncomfortable one.

WolfmanBEan / December 4, 2008 10:25 PM

I can top them all. Now most people contract some form of food poisoning at least once a year. Most of the time the symptoms are mild, and can even be mistaken for a 24 hour flu bug. Other times, the symptoms are similar to one having a very bad case of the flu, but rarely do people ever need to go to the hospital for food poisoning.

Just by its nature, the probability of contracting food poisoning from fish is always higher than most other foods. This is why, based on personal experience, I recommend that no one ever engage in anal sex after your date ate a large fish dinner.

We hadn’t been dating that long, only about a month. Even though we'd only been dating a short time, we were having sex since the second date, and it was the best, freakiest, porno-style sex of my life. Seriously, this was the kind of sex that every man, deep down, dreams about having at least once in his life. It was the kind of sex that I had wished for ever since my voice started changing. It was with this woman, and only with this woman, that I was ever addressed with the phrase, “Use your whole fist for Christ’s sake.”

On one now infamous date night, we were enjoying a romantic dinner at an upscale seafood restaurant. Through the entire meal, however, sex was all that was on our minds. In retrospect, every date we ever went on seemed to just be a temporary diversion from the best part of the night, which involved animalistic insertions, feral lickings and brazen misuse of food products. We emptied wine bottle after wine bottle over the course of the dinner, and by the time the main course arrived, fish for her and lobster for me, she slipped off her shoes and casually masturbated me under the table with her stocking covered feet. Completely plastered and horny by the end of the meal, we decided to skip dessert in the restaurant because a much sweeter dessert “was being prepared in her hot, wet crotch,” she said. I paid the bill and narrowly avoided getting a speeding ticket, not to mention a DUI, during the drive back to my place.

By the time we got into my apartment, we were tearing each other’s clothes off. Sloppy in our drunkenness, we knocked over two lamps during our horny, groping journey into the bedroom. Once in the bed, she got down on all fours, arched her back, and presented her delicious ass to me. I grunted my approval while aiming my rock-hard cock missile at her hairy silo. When the head of my cock began to penetrate her lips, she stopped me.

“No. In my ass,” she hissed at me, sounding both horny and angry at the same time.
“Are you sure,” I asked?
She giggled as she said, “If I could handle last night. . .”
Oh yeah, I thought. Last night’s adventure involved a clown mask, three packets of Pop Rocks, and a twenty-inch replica of the Eiffel Tower. What the hell was I thinking? Of course she could handle some anal-action. She reached between her legs and began lubing up her asshole with her own pussy juices. Where did I find this girl? I thought. I was in horn-dog heaven. Blessed. Not being an expert in anal intrusion, I slowly eased my way into her lovely stink-star. First the head, then a quarter of the shaft, and soon I was buried to the hilt between her ass-cheeks.

“Go slowly,” she said, half moaning, half panting in both pleasure and pain, I think. I did as she bid, and very slowly began pulling out, like a steam piston on an old locomotive beginning its first run in a century. Almost all the way out of her, but keeping the head firmly planted in her ass-iris, I slowly began inserting again.

“Yeeeeees!” she moaned and began diddling her clit. Soon she said, “Faster.” So faster I went, the tempo increasing until the train was running at full speed, the piston pumping in and out so fast my cock became a complete blur, her hand rubbing her clit like she was trying to start a friction-fire in her pussy.

“Gnnnnnnnah!” she screamed. Thinking she was close to orgasm, I pumped that ass even faster, faster than Amish meth-head churns butter.
“Gnnnnnahstoooop,” she screamed, or something like this, because the noise in my head was drowning out the reality around me, for in my head I heard a steam locomotive, chugga-chugga-chugga-chugga-Woo-Woo! Barreling down the tracks, and somehow I pumped even faster.
“YES!” I screamed.
She started reaching behind her and flailing on the bed in what I thought was ecstasy—
“—Stop!” she screamed, able to finally get out the word I had mistaken for groans of ecstasy moments ago. She screamed this with such volume and guttural, primal force that it had the effect of pulling the emergency brake on a 100,000 pound locomotive running at full speed. The sex act squealed to a halt, and I pulled my cock out of her ass like the rip-cord on a parachute. Did someone order champagne? No, that popping noise was my cock coming out of her ass.
“Arrrrrrgh!” She screamed, as I yanked my cock free. And then it happened.
Immediately after my cock popped out, I was sprayed from belly to thighs with watery, fish-smelling diarrhea.
“What the—-?” I said, not able to get the word ‘fuck’ out of my mouth because of my shock at the brown funk lining my body. As she sprayed me, she seemed to be propelled forward by the force of the jet-propelled diarrhea, and she collapsed onto her stomach.
“Oh. My. Fucking. God.” I murmured, completely shell-shocked. Everything was still. I could hear my wind-up alarm clock ticking on my dresser. I stared at my shit-covered body. I surveyed the room to see if there was any collateral damage. The trajectory of the diarrhea spray was similar to buck-shot in a sawed-off shotgun; it was everywhere. Unfortunately, during the sex act she had been facing the feet-side of the bed, which meant that the headboard, my bedside table and lamp had poop on them as well. Even my bedside clock had a few speckles staining its face. The bed sheets: Killed in Action. A total loss.

I looked at my date, lying there motionless. I called her name. No response. I called her name while shaking her a bit. Nothing. Fear shot through me, as I thought, “Oh my god, what if she’s dead?” But this fear quickly dissipated when I heard her snoring. She was passed out from the wine. I on the other hand was no longer blasted drunk, because the blast from her ass rendered me completely sober. This night was definitely going down in the (ahem) annals as the all time worst date of my life. In fact, I had to invent a new special category, “Even the Devil would feel sympathetic,” to describe this night.

I cleaned up. I cleaned her up. I cleaned the headboard, the dresser, the lamp and the clock. With some manipulation of her passed out body, I was able to wrangle the sheets from the bed and throw them down the garbage chute. By two in the morning, I found myself lying on my couch, drinking Jack Daniels from the bottle. I don’t remember passing out myself, but I can say that unconsciousness didn’t come soon enough.

“It was food poisoning,” her voicemail message explained to me the next day. After some silence, she added, “The fish.” More silence. “Sorry.” She left this message the following day, around 2:00 p.m. I had slept until Noon, and, thank God, she was gone when I woke up. How do you face that? She never called me again. I never called her. I definitely learned two valuable lessons that night: 1) Never have anal sex after a sea food dinner. 2) Be careful what you wish for. There’s only one other experience in my life that entered into the “Even the Devil would feel sympathetic” category, and frankly I don’t know if I’ll ever be able to tell that story. Let’s just say that the morning after a great one-night-stand, the beautiful woman you banged the night before can certainly use your bathroom. . .but she shouldn’t be more comfortable standing up while she pees.
That was a the most embarrassing date.

Rusty / December 10, 2008 7:26 PM

I met this girl online and decided to give it a try. Our first date we went paint balling and had an OK time, but it was a little awkward since she had a hard time talking to me. She asked me to go to the movies with her later and I agreed. we met at a mall since I didn't know the area and she wanted to drive. I met her there and found out she brought her ugly friend, which was fine.
She drove like a maniac! I had never been so afraid to be in a car before. And on the drive her and her friend had a belching contest. I was sitting in the back seat wishing I had just insisted on following her so that I could take a wrong turn and never see her again, but I was now along for the whole ride.
Once we got to the theater she ordered three tickets and looked at me waiting for me to pay. I would expect to pay for my date and me, but not the ugly and disgusting friend. I paid and we went inside and found our seats. I tried to make light conversation while waiting for the movie to start, but I had a really hard time doing that since her friend and her were text messaging each other rather than talking.
During the movie she started to lean towards me more and more. I started to notice the strong smell of B.O. intensifying as she got closer. I couldn't help but lean the other way as much as I could to be able to breath.
The movie had to have been 3 hours long. I could not wait to get away from her.
After the movie we all got in her car and started to drive away. I was very silent during the drive back. I was so angry that I had agreed to let her drive and that this date was so horrible. She started to yell at me for being so quiet, and I had to hold my tongue to not say anything rude back to her. Once we got back to my car I almost jumped out of her car while it was still moving. I ran to my car and sped away, never talking to that disgusting ogre of a woman again.

Bull / December 10, 2008 9:00 PM


You probably shouldn't try to pass off a story that's been circulating around the Internet for at least 5 or 6 years as your own. Google to the rescue.

Gianna / December 10, 2008 9:50 PM

Less of a date and more of a complete horror story of high school romance...
Being a nerdy, brainy, and somewhat shy girl, I didn't start dating until Junior year of high school. I had plenty of offers, but was just too intimidated by guys and the whole dating thing to give it a try.
This didn't stop me from flirting all through high school with a guy a year ahead of me. We started dating (finally) in my Junior year. During my Senior year, I'd sit in film studies gushing over our great relationship to a classmate.
She, in turn, talked about how she hated her boyfriend, and had sex with him right before dumping him. And she felt kinda bad... Oh, no, not really.
A couple weeks later, she started sharing stories about a new love interest that had been "distracted," but noticed her when she spread her legs to reveal her crotchless panties. I hadn't been familiar with crotchless panties before that day, and was mildly horrified at her method of seduction.
After a while she told me she had initially gotten with the new boy just for the sex, but was beginning to actually like him. Good for her, good for him; whatever floats your boat.
Graduation came up and I had sent invite and called my graduated beau, to no avail. Come ceremony time, I was in line for the procession when he came walking in the door. I skipped out of line to give him a hug and tell him I was glad he had come; the hug he returned was remarkably stiff... Curious.
The easy classmate I discussed earlier ran up to my high school sweetheart and gave him a sloppy, tongues-everywhere, twist-your-stomach, HELLO-your-parents-are-watching kiss. He gave me a small shrug, traipsing off after her like a puppy.
The entire time we shared relationship stories, we were talking about the same guy; much to her knowledge.

Years later, I had a drunken encounter at a party with my "sweetheart." We made out, and it was worth it (he always was an amazing kisser), but when it came to him unzipping his pants, I laughed and told him, "Not after you were with that nasty, nasty h*e" and then proceeded to hop in a cab and snuggle into bed at home.

Jessica / December 10, 2008 10:18 PM

We had met over the internet, and despite his voice sounding a bit off, we seemed to get along great. I invited him to a business event of mine, so that after the event, either of us could ditch without it being awkward. I told him he didn't have to dress nicely, but that it was a big deal for me and my organization.

Not only did he come in late, partially disrupting the event but I noticed him sitting in the very back.

Not unusual, until I saw him knitting. He brought knitting on a first date, at an important event. Not only did I notice, but so did all of the professionals.

Oh and he sang Nickelback on the top of his lungs in his car, stating "Nickelback is the best band ever!"

Needles to say - it didn't work.

frankie / December 10, 2008 10:23 PM

I was dating this guy who was a little rough around the edges, but seemed nice. One day, I introduced him to my friend and we all went out for drinks, then back to my house. He kept touching my friend (who had pretty much passed out at that point) and I told him to quit it. He didn't. I told him to get out of my house and he was like, "Hey, I'm a guy, I'm with two beautiful women, I should try it, right?" Wrong. I told him to leave and went to take a shower. When I went back to my room, he was still there - with a condom on his erect penis, trying to take off my friend's clothes as she tried to fend him off. I couldn't sleep in my own bed for a week after that.

Tony / December 11, 2008 12:20 AM

I went on a date with an Asian girl I met online. She sent nice pictures and claimed to be 25 years old (I was 28). I took her to a nice restaurant, and we met there. Turns out she was lying about her age, the pictures were really old. She looked more like 45, now overweight, and she could barely speak English at all. I could just sit there trying to repeat simple English sentences over and over again until she finally gave up to understand with a smile revealing some pretty nasty teeth. I tried to hide in a happy place in my mind until the torture was over, and escaped quickly after. :(

Emma / December 11, 2008 6:09 AM

He came up to me in the mall. I was defenceless: I had such a monster headache that I could barely see. Got his number, gave him a call, we had dinner.
I think the standout moments were him not knowing who Andy Warhol was, and the rhetorical questions.
The really great moment: "So, if you were an animal, what kind of animal do you think would best describe your personality?"
(He was a fox - cute, sneaky, arrogant. He didn't mention short, but that was applicable too).
Apparently I was a panther - mysterious, but with claws. Just because I told him his arts degree came from a truck.
Then he treid to kiss me, twice, talked about naked Twister and didn't understand the subtleties of body language.
He phoned me later and said "I don't think it'll work out long term."
I said "I completely agree," hung up, and deleted.

Kelly / December 11, 2008 10:58 AM

My freshman year of high school a boy I had an enormous crush on asked me to the homecoming dance. there was a quick dinner then we headed over to the dance.

a few hours in I started to feel sick so I nipped off to the ladies room where I proceeded to spew into the toilet for a quarter of an hour. I finally called my mother for a ride home.
as I was waiting outside for my mom I felt another visitation for my tummy monster.

a short aside: when it snows my high school spreads gravel to break up the ice rather than un-environmental salts. it had snowed a few days before but had melted (the gravel stayed)

as I was running in stilettos and a little red dress towards the school and the bathroom I stepped on a patch of gravel. my feet flew forward and i landed hard on my tush breaking my tail bone. I then leaned over and puked.

My date didn't even bother finding out where I had gone until her saw me limping at school the next Monday.

Levitra / December 11, 2008 11:13 AM

Mine was definitely my high school prom.First of all my date left me mid date for someone else in the limo. Then she embarrassed me even more with her disgusting behavior. It was awful

Curly bassist / December 11, 2008 11:35 AM

Came across this girl at a gig I was playing at, we hit off straight away and were chatting for a wee while (her bringing up the subject of her recent ex...should have seen that warning bell!) and she said I seemed like a nice guy and that she'd like to meet up some other time. Cool!

She suggested that since my bands' next gig was in her home town, we could hang out afterwards. I turned up, kept an eye out for her during the show with the intention of getting her a drink, only to find her all over aforementioned ex. Funk-a-doodle-doo.

Worst gig and worst potential date!

josh / December 11, 2008 12:54 PM

I met this girl online. We went out to dinner which was decent. Conversation was fairly easy and normal. Then we went back to her house to watch a movie. We were there for a few minutes before she got a phone call. She told me she had to meet up with one of her friends downtown (I didn't ask why) and decided to go along with her for the ride. Next thing I know, we're in the sketchiest part of Baltimore, and entering into a club/bar where the bartenders are behind plexiglass. She found her friend and another guy, and we then drove from the bar to some side street a few blocks away. There were cops at a nearbye intersection, so we pulled around the block. We waited in the car for at least 30 minutes while the one guy walked to meet up with someone to score some kind of drugs/pills (still not sure what they were). Then we had to drop him off at another rowhouse to make a delivery, before dropping him and the friend off back at the bar before getting to go back to her house where she proceeded to take her pills and pass out and I proceed to leave.

Scott / December 11, 2008 1:06 PM

I was in 10th grade... first date ever, could only get better from here.

This harpy of a girl - obnoxious, loud, obvious - wouldn't stop bothering me and finally asked me out. I stupidly obliged.

Her father (who looked to be approximately 75 years old and probably related to the Cryptkeeper) picked me up and drove us to the movie theater. The girl and I saw "What Women Want," which is probably one of the worst movies ever made. The whole time she kept dropping her Chap Stick on the floor and I just looked at her until she slammed her shoulder into mine and frowned for the last third of the movie.

We get back into the car and she asks her nearly-infirm father, "Hey Dad, what does it mean when a girl drops her lip gloss on the ground? Huh? What does it mean?" then gives me an accusatory glare in the backseat. I said not a word on the way back and never struck up conversation with her ever again.

Perhaps somewhat consequently, I now date men =D

Jim S. / December 11, 2008 1:47 PM

My wife and I got married in early Dec. For our honeymoon we went to Hawaii. After a beautiful morning and a very nice breakfast we went down to go see the ship. We were looking to see some things it was early so there wasn't anything going on. We were about to leave and then we looked up a show some planes coming in my wife remaked to me that it was an airshow! We stood there and watched for the show to begin.

We found out a few minutes it wasn't an airshow.

dd / December 11, 2008 4:25 PM

A few years ago, I met a very beautiful girl through my gf and she gave me a link to her blog. Time passes, I break up with my gf and I stumpled on her blog. I sent her an email, she replied, we exchanged a few more flirty emails. Then we sent some more emails, naughtier, sexier and then we agreed to meet... It was just obvious that we would end up having sex on our date...

A year passed since I met her and I haven't seen her since. I was worried that I might not recognize her. I only remembered her amazing green eyes. She arrived at my flat. It was her! I recognized her eyes! I actually recognized only her eyes as the rest of the body changed... a lot! She must have gained more than 30 kilos! [how can someone gain so much weight in just a year???]

I didn't say anything about it. I acted immediately and told her we were going out for a drink. I didn't want to stay home with her, maybe she would get ideas from our emails!

So, we went out, had a drink, talked socially, we had little fun and then we returned at my place. I parked in frond of the building, I told her I had to go to bed because I had to wake up early the next day (awful lie I used to wake up at 10), kissed her on the cheek and went home.

She wrote a post on her blog about her "amazing" date and I never talked to her again!

Molly / December 11, 2008 4:40 PM

My sophomore year of high school, a few friends hooked me up with a senior who I kind of had a crush on for our semi-formal dance. Not only did he not dance with me the whole night, but afterward he ditched me saying his friend was having a "family emergency". It turned out that "friend" was his ex-girlfriend, who he asked to prom the same night.

A few years later, my brother saw him at a party, and he was really drunk. He started bragging to my bro that I was "obsessed" with him in high school and that I "so wanted him".

Dude, you look like Mickey Mouse, and I only liked you for a week... Jerk.

awkwardme / December 11, 2008 10:30 PM

We met at a psychiatric hospital (no joke) i was in for deppression and at the time i dont know why he seemed pretty normal to me. We exchanged numbers and when i got out i excitedly called him to find out he had told his mom about me, and she was the one who answered the phone. A few weeks later we decided to go to the movies, we ended up watching some crappy Christmas movie. As expected he asked me to kiss him so i did and that was when it happened i suddenly felt his tongue in my cheek and half of my face was covered in saliva, then he tried to put his hand inside my pants. Needless to say, i never went out with him again, and never talked on the phone again, with him or his mother.

Danielle / December 11, 2008 10:53 PM

The worst date I have been on was my sophomore year in college. I was working as a server in a restaurant, and a busboy had asked me out. I was just getting over another co-worker, which he knew about, but I figured, he's nice enough, and very cute, so what the hey. Our first date was a lot of fun, we had gone out and had a great time together. So, I invited him to my apartment for a movie the next week. In the meantime, I also invited him to a Halloween party the night after our cheap movie date. So, we go to Blockbuster, and pick up some movies. He suggested all these weird, un-date like movies, and after turning most of them down, we finally agreed on something and proceeded to check out. He had the account, but asked me to pay. I paid, we proceeded to drive to my apartment. While watching the movie, he was staring at me the whole time, and when I would ask him what he is looking at, he would say "Nothing," and watch the movie for a few seconds, and turn his head back to me. After he had done this three or four times, he just asks if he could kiss me. I was feeling quite uncomfortable, and made the excuse I was still not over said co-worker, so, no, sorry. After that statement - he shoved his tongue down my throat. Ugh. We finished the movie in an uncomfortable silence, and he left. With a hug. Unfortunately, this is still not over, as I dumbly invited him to party with me on Halloween. My friend and I were getting ready, and he calls me and asks if I can pick him up. He lives 45 min away. I asked if he could get a ride and he states definitely not. So I have to go pick him up with trays of jello shots in my car! When I get there, he is dressed in full on camo/army uniform, and comments on how I was not dressed up (I was a *sexy* schoolteacher - I know, not so original) And gets in the car. I meet my friends and introduce him to everyone, and he barely talks at all. Instead, he stood *literally* against the wall the whole time. I tried to engage him as much as I could, but nothing worked. When he decided he wasn't having a good time, standing against the wall he asks me to take him home. It's only 12:00. I take him home, and there was silence all 45 minutes. After we arrive, he still has the idea I would want to kiss him, and go out with him again. Needless to say, I didn't, and we barely talked again.

Bahb / December 12, 2008 2:13 PM

Is it bad when you go out on a date and part way through they say, "Oh! You thought this was a date? That's cute..."???

Molly / December 12, 2008 3:47 PM

I was dating a guy for a while, but I had to study abroad during college because it was something that was really important to me. After five months, I got ready for a passionate embrace with him when he would pick me up at the airport in Minneapolis (after a very, very long flight and no sleep). When I got to the airport, he was nowhere in sight. I kept hoping he would pop up randomly and surprise me, but after about 30 unanswered phone calls and four hours, I had given up. My mom was going to pick me up then...which would have been just fine if she didn't live four and a half hours away from the airport. Suddenly, my boyfriend calls me and claims that his phone was on silent and he just woke up and got my calls. Not the best way to welcome your girlfriend back into the country.

danielle / December 12, 2008 4:11 PM

well... i met him at my friends going away party, and he was not at all my type, but the next day when he called me, i was a little bummed about my friend leaving, so i agreed to hang out. big mistake.i knew as soon as he said he had no car, that i would have to come pick him up, almost an hour out of my way, that it would be an interesting night.

so i picked him up. he was a lot more... "thug" than i remembered. he said hed left his car at the party last night, and asked if we could go back there so he could get stuff out of it. aside from the fact that it was an hour back to the car, i pretty much agreed because i was too in shock regarding the guy that i had just picked up. On our way back to his car, he asked if i wanted to watch a movie. I asked which one, to which he replied XXX. I said id already seen it, and he so kindly informed me that it wasnt the vin diesel movie, but it was RATED XXX. i declined.

we finally got back to his car, and he asked me to put the top down on my mini, so i did. at this point, im pretty sure i witnessed a car being broken into. he took a big black bag from the back of the SUV (which he opened with a clothes hanger), and put it in my trunk. while he was doing that, i called two friends. i told them to call me at 9:30, and bail me out.

so were leaving my friends house, and my top is still down. my pink slip flies out of the back seat of my car. lovely right? so we pull over and look for it, and he attempts to lure me into the orchard, because "he sees a party going on in it" and "we should just go check it out!". yeahhhh....

SO we find the pink slip, get back in the car, put the top back up, and i start driving back towards his house because to me, the date was over. and my amazing luck? i hit, not one, but TWO cats. at once. yeah, i was a little freaked out by that. so i pulled over for a little bit haha and he decided that would be the most opportune time to kiss me. Eww.

my friends finally call, luckily while he was trying to get me to drive to sacramento (only another hour and a half away!). and i make up some story about how i have to go help a friend move, in fresno? Im clearly bad at thinking on my feet haha. then he wanted to go too! so i had to basically drive him back to his house against his will.

at one point, he took one of my CDs out and put in one of his own. worst music ever. but ill come back to that later.

we get a few blocks from his house, and he decided to inform me that that big black bag from earlier? its full of guns. im like oh. wonderful. so now im just a LITTLE freaked out, and hes like, "i gotta gun in my pants too.." and i ignored him, "wanna go shoot it?", ignored him, "wanna just go touch it?", ignore, "wanna look at it...?"


so i finally get him home and i have to coax him out of my car.

thats it, hes gone, this ridiculous night is over right? wrong. im on the phone with my friend telling her about it, and i realize his CD is still in my player. i take it out, and reach down to put one of mine in. they're all gone.

yep. he took em. every single one, a book of probably close to 100 CDs.

then he called me, asking if he could get his back.

it was not fun.

stu / December 12, 2008 5:32 PM

This one is kind of my fault….
My friends (2 couples) came to spend a week with me in my hometown in Croatia. We had a great time and one evening we were wondering if I were able to shotgun a 1 Liter (33.8 oz) bottle of beer. I sure as hell destroyed that thing in one chug and suddenly realized I was already 10 min late for my date with a local girl. At that time I was still in my swimming shorts (hey, it was a summer vacation).

When I arrived (now 30mins late) she already looked quite pissed, but what followed should have made her turn around and leave me instantly. At this point the alcohol really kicked in and instead of apologizing I started laughing my ass off in a loud and obnoxious manner…on the center square of the city with more than two handfuls of people around us. Must have been really embarrassing for her but I got my shit together after 10min and we continued with the date.

Later that night my friends joined us and I began criticizing the local government which my patriotic date didn’t find amusing at all. So this big fight started and stubborn and still drunk that I was I insisted on my point (I admit being an asshole sometimes). I is still a mystery to me how I actually turned her opinion on the subject, made her apologize for being a pain about it and we ended up having (great) sex that same night at her place.

We continued dating for a while but the long distance thing didn’t work out…imagine it was not the date that destroyed it.

Marie / December 12, 2008 5:43 PM

The worst date I've ever been on had to be Valentine's day a few years ago (with my then boyfriend of two months.)

We both lived in the burbs, but I live closer to Chicago so we decided to take my car. He ends up driving because I'm not the best city driver (I later found out he wasn't either!)

We had plans to have dinner at this restaurant he had been 'hyping' the whole night so I was pretty excited thinking it would be a nice Valentine's day.

Well, he ended up underestimating traffic ( a 20 minute ride turned into a 55 minute one) and parking in the Wrigleyville area is nearly impossible, so, after 30 minutes of searching he pulled into this lot that charges you $20.00 to park.

Q. Guess who pays?
A. me.

The restaurant he was hyping... just some hole in the wall cafe that was overpriced..

Q. Guess who pays?
A. ME.

Oh, but he had no problem leaving a crappy tip..

I quickly let him know that I was upset for spending over $60 on Valentine's day, so he offers to pay for gas... we drive back to the burbs... he pulls into a gas station and he starts to pumps the gas but I noticed he stopped rather quickly.

I looked at the gas pump and $8.07 blinked.

A week later I drop him the 'I need time' phrase..

Eamon / December 12, 2008 6:02 PM

Never had a bad date except for the ones that were my fault, and I'm so not going to share those.

kteam / December 12, 2008 6:45 PM

the night after my 21st birthday, my roommate dragged me with her on a double blind date... that i didn't know about. we'd made plans to go to the bar with her "friends" who, i later figured out, were two guys she'd never met before (i still don't know where she met them!) so dudebro #1 is all about my roommate, talking very loudly about what a freak he thinks she is in bed, etc, making me very uncomfortable. dudebro #2 buys me a couple of drinks and we make pretty painful small talk. i ran into another friend at the bar (thank god) and had a cigarette outside with her. while we were in the middle of an animated conversation about a professor, dudebro #2 comes up and says, very loudly, "i'm about done waiting on you." "excuse me?" i replied, trying to stay patient and polite. "i mean, unless you wanna go back to my apartment and make out or something." i told him i'd pass, to which he said "fine, you're an uptight bitch anyway!" at this point, he turned around and stormed off... into a waiting taxi. keep it classy, pensacola.

ant / December 12, 2008 7:26 PM

My best friend was out of town and his gf had free tickets to the premiere of bourne ultimatum…no, sorry guys, it’s not heading that way…

She brought a gorgeous classmate from med school and I fell in love instantly. We had a few laughs and she seemed to like action movies (big big plus!). After the movie I asked for her number and we texted a few times to find ourselves back on a movie date.

Unfortunately I had to work the night before that and was up for 28hrs at the time we met. I ordered the tickets by phone but the cashier of course messed up and the movie I picked wasn’t showing on Saturdays, leaving me looking like an idiot. We picked another film that started 2hrs later and went for a drink where we got seats outside (on a chilly September day). I got impatient when she couldn’t pick a seat and rudely told her to just sit down pointing to a chair. The whole conversation from then was horribly awkward and one could see from miles away that we were losing the game.
Then we decided to grab food at a place she knew just around the corner.

Strangely, once we sat down at the other place, the whole thing turned 180°. Suddenly our eyes met all the time, our voices became more relaxed and the whole atmosphere went from ice cold to romantic. We talked about everything, went to the movie, which was great, I took her hand and she snuggled into my arm. Although my attempts to kiss her during the movie and when saying goodnight didn’t work out she invited me to her place for dinner(that I cooked and brought) a few days later.

We’ve been together since then and she is doubtlessly the love of my life. I’m writing this to kill the time until I can see her again. 11 days left of my 6 month stay abroad.
Just an example how dates can start out horrible and turn into something great.

Jim the Mullins / December 12, 2008 7:26 PM

Took a blind date recommended by a "friend", out for a little dancing. Little did I know she was hammered from the start. In a local Bar she danced around so drunkenly she took the blinds off the floor to ceiling glass walls. Major embarrassed. I got her back to her home despite a near fatal crossing of a roadway. Remarkably she was still into it. Despite being a twenty year old horndog, I passed. Not into alcohol necorphelia. Never saw her again and quikly dumprd so called friend.

Amy / December 12, 2008 8:10 PM

In response to reading like 95% of these in one sitting:

A) Why are so many of these posts about Chicago?

B) Please stop saying 'needless to say'..SO overused!

C) Entertaining stuff, thanks everyone.

Blue Mountain / December 12, 2008 8:52 PM

I was going on a second date with this guy I had met in a club in Itaewon, the really sketchy part of Seoul. He's really hot, so I decide to bring him back to my apartment because he's living with his mother, not such an uncommon thing for a single Korean man, even though our date was in Seoul and my apartment was an hour bus ride to the south.

He'd been drinking quite a bit but I didn't really realize how bad it was until we got to my neighborhood and he insists on going to the local grocery store and buying a shopping cart full of groceries. We get back to my apartment and have sex, which isn't very good since it seems that all of his experience comes from watching pornos.

Then he proceeds to sleep until 3pm the next day. I ask him to leave my apartment and he starts crying and asking me why I don't like him. I don't mention that I had been on the phone with a friend and discovered that he was the ex of another friend of mine and had had sex with her but then claimed that he hadn't because he was Christian and too 'pure' to have sex without getting married. I did mention that we had nothing in common, that he seemed to have some problems and that we just lived too far apart. He then refused to leave my apartment until I threatened to call the police.

anastasia / December 12, 2008 10:05 PM

I had two tickets for a concert at the House of Blues, so I offered one to this guy I'd been seeing for awhile. I ended up driving the three hours there and back, while he quietly stared out the window. We stopped at a TGI Friday's to eat dinner before the concert, and conveniently his card was declined. When I looked disappointed, he said "What you can't buy me dinner?" I reminded him that I was paying for the concert tickets and gas. Ten minutes later he finds a twenty dollar bill on the ground and instead of paying me back, pockets it. At this point, it started raining as we were standing in line to go inside. The concert was awesome, but the date... not so much.

Odobumbe Mumtimbo / December 12, 2008 10:08 PM

Telling this date story will hopefully be cathartic, so.. thanks.

It starts off in my house. My date is there, sipping on some wine, petting my dog, Muctukcu. I excuse myself to freshen up. Upon my return, I find my date molesting my dog with a candy cane.

So, we go out to dinner. Of course, I am a little upset. Not at her, but I do not want to pay for dinner. To cheer me up, she offers me the candy cane. Of course, I take it. It was the best candy cane I have ever tasted.

This magical woman is now my wife.

Annie / December 13, 2008 11:22 AM

I was newly single and met a hot guy at Bennigan's. We chatted for a while and he told me he wanted to spend some quality time with a girl before he shipped off with the Army. He was a basketball player, he said, but had given it up to go to join the forces. Seemed valid enough, as he was well over six feet.

SO. Somehow I agree to hang out with his friends afterwards. I told him I couldn't drink anymore so that I'd be able to drive, at which point he assures me he'll drive my car and I'm welcome to keep chuggin those Cosmos.

Fastforward to the drive. I'm sloshed in the passenger seat and he's going about 100 on the freeway. I beg him to slow down and he laughs and CHANGES GEARS while driving. My poor automatic transmission was not happy. It was screeching and bellowing, just like me. "HAVE YOU EVER DRIVEN A CAR BEFORE?" I asked. He said, "I drove from New York to California once." So there I was, drunk, and in the speeding vehicle of someone who had only driven once, probably didn't have a driver's licencse and certainly wasn't doing anything good for my engine. I begged him to pull over and he refused. I gave up and sat quietly. And terrified-ly.

His friends also lived 45 minutes away, which I didn't know before getting in the car with Mr. Maniac. His friend had taken in a stray Labrador who was obviously scared. Tail between the legs, wary of all the strangers, but overall very cute and well behaved. One of the drunk boys got too close to his face and he began to growl. MY "date" took a running start and kicked the dog so hard that he was airborne.

I took that as my cue to drive the 45 minutes home, ignoring the 11 times he called me saying he had never felt so strongly about a woman. And please, please, please, would I come back and fuck him before he left for the Army?

Annie / December 13, 2008 11:25 AM

PS- Forgot to mention that he was kicked off his basketball team for ACCIDENTALLY KILLING SOMEONE. The army was an alternative to prison. Very nice.

Annie / December 13, 2008 11:26 AM

PPS. The new transmission cost me $2,700.

Lisa / December 14, 2008 2:22 AM

Ah...where to begin.

I met a guy online, he looks like a nice, clean cut, military guy. He tells me that he's 5'4", 24, 130ish lbs. I agree to a date, because he seems to be able to hold up his end of a conversation. He shows up to my dorm in a hunk of crap car, complains that he had to take back roads the entire way there because his car can't go more than 35 mph. Then he gets out of the car. If anything, he's 4'5". And he has to be at least 40, he's almost completely bald, and I'm guessing he was around 180 lbs. I decide to give him a chance anyway, because ya know, looks aren't anything. BAD IDEA! He comes up to my room, we chat, I have to go to class. He INSISTS on going with me. Random, but we go to class, then return to my room. Proceed to chat some more, and then he begins insisting on calling me "Goddess". He then whips out a pair of handcuffs and asks me to stick my thumb up his ass. He's promptly informed that I have a large research paper to write, and that I'm going to the library ALONE. He kept trying to email me for the next 2 months.

Then there's the gent who was 30 years old, and couldn't drive. I decided that maybe he just didn't own a car since he lived in downtown. So what the hell, I go and meet him at his place and we're supposed to go to a movie. I walk in, the place is literally WALLPAPERED in porn. (the hard core stuff) He then asks me if I want to watch a movie...I look at the collection, and all he has is porn. I turned around and walked out.

Then there's the weird 40 year old Jewish doctor...on the first date he gave me a tour of his house, saying "and this is where the babies will sleep", etc. and then asked me if I wanted to go and pick out a ring.

HA! I sure know how to pick 'em.

Hahaha / December 14, 2008 4:46 PM

Ok, upon reading these very very entertaining stories, I was struck by :
A) the amount of girls subjected to "tounge-darting".
B)The unsavory amount of emotionally unbalanced men in Chicago!
And C) Odobumbe Mumtimbo / December 12, 2008 10:08 PM comment is sooo Strange!!!

The worse date I ever had was when I was about 19 on a gap year, I had made friends with this guy from my new job, he was a bit eccentric, but had a great sense of humor, was good looking and seemed the wall flower type.
I supposed I liked him because he showed a lot of interest in me. Which by the way girls, is a bad thing to go by, any way, we'd talk at the pub, when we had drinks after work on Friday's, and we'd get along great. I had drank a little too much one Friday and we ended up going to another bar- to meet a friend of his- I was aware of how inebriated I was when I came into the light and caught my reflection in the mirror- messed up! I remember thinking to myself that he was considerably more sober than I, It took a while but I made the responsible and conscious decision to get my self home to bed!!- I explained that I was too drunk and left, he walked me to a taxi which was nice and I shuffled into a taxi murmuring my address.

I got a couple of texts over the weekend and inviting me out on dates over the week but I declined. Monday came and I went back to work, I noticed that he wasn't there, so I felt a bit less awkward about needing to make friendly conversation when things felt as though they were in limbo During work on Monday he sent me the most shocking text message which described an elicit sex scene he had about me, an older female employee at work, and him. Oh please send me more messages like that on a regular basis so I can feel attractive and horny?!? The next day he apologised profusely and said it was a joke, I guess when he's in person he kind of redeems himself, so I didn't hold the text message thing against him. I agreed to meet up for drinks with him about two months later- We went to a bar near his house, I was a busy night and kind of crowded, everyone was mashed into one another, which was ok because as far as I was concerned, it wasn't a date- he know that too.
During the night he told me about some psychotic ex-Girlfriends he had, one in particular, sending a picture of an Ultrasound to his mother (He lived with his folks by the way) that she had printed off the internet and claimed that it was the baby she was carrying for her son. I thought, what a psycho!! After lots of drinks, I remember thinking wow, I'm so drunk and tried to get myself home.

The last thing I remember about that night was me searching for my wallet on the street, with the contents of my bag on the ground. This was not like me. I never felt like this before. To this day I believe he drugged me, put something in my drink. I woke up at 4pm(SO DRUGGED ME) the next day in his parents house naked from the waist down in his bed. Missed work that day.My head was not right until the following day- My wallet also gone. I was Freaked!!! The night is still really patchy. I left my job, lost my phone that night too so I didn't have any contact with him.

That night was the absolute worst night of my life let alone date. I never told anyone about it. I felt like the biggest idiot for putting myself in that position, and I want let people know that you gotta be careful.
I seen him once, about six months later he was on the bus with his friend, I heard his very characteristic laugh and when I heard it, it sent shivers down my spine- I completely ignored him trying to remain out of his vision, and I realized that he was talking about me to his friend, and they were laughing about it. I got off the bus, but have afterisms about how i'd go up and punch him right in the face. Asshole. That was 4 years ago now and I'm in a 2 year relationship with the greatest guy ever.

Not some freak, idiot,nympho! Ahhhhh! It makes me so angry!!! Hey we all make mistakes- I wish however I had a funny one to put up instead of this horrible one. Thanks for the entertainment.

anon / December 14, 2008 7:16 PM

My worst date was a series of visits with a guy I met online. He looked good in his photo, I remember complimenting his outfit. And we could talk for hours over the phone. He drove quite a distance to see me, so we planned to meet up at a restaurant, then he would follow me back to my place. When we met in the parking lot he ran to me, picked me up, swung me around, and kissed me, like something you'd see in a movie. Strange, yes, but I had just come out of a relationship with a guy who never showed his emotions, so I thought it'd be nice to date a sensitive guy.

For a gift he brought me a Cabbage Patch doll he had from childhood. I told myself he was just being sentimental. Did I mention that he was wearing the same outfit from his picture that I'd complimented him on? The next morning (he slept in the guest room) my roomie caught him spraying his clothes with Febreeze and putting them back on. When it was time for him to go, he laid on the floor with his head in my lap, sobbing. I should have ended it then!

The next visit he gave me a "promise" ring and wrote me a really sappy poem with lots of spelling mistakes. He also made me watch hours of anime he had brought on VHS tapes. It just got weirder and weirder after that. He even wrote me an erotic story about what we would do on our honeymoon. I finally broke up with him via email and sent his ring back.

Mo / December 14, 2008 7:23 PM

I went on this one date in high school that was particularly terrible. I was a junior and he was a sophomore. He asked me to prom but I had to buy the tickets because I was the junior and he would technically be going as my date (He was "going to pay me back"). We went with another couple. As soon as we got there he said we had to walk around and show everyone "how pretty I am" (by this he meant himself). Then when the dance ended he ditched me to ride in a limo with a bunch of his friends leaving me to be the third wheel with another couple. He also never ended up paying me back for the tickets. What a jerk.

robert / December 14, 2008 9:44 PM

In high school, I met this girl over the internet and honestly just thought of us as friends. An old neighbor of mine was having an art show in a city that was about equal distance from where each of us lived. I briefly mentioned this to her, but she took it as an opportunity to invite not only herself, but her entire family. I thought we were just going to say hello and talk, and leave it at that. When I got there and met her she explained how she took the day off from school to buy a new dress and get her hair and nails done- which should have hinted that she intended that our encounter be a little more than a hello (although she did look very beautiful). I met her mom and grandmother (her dad was apparently in jail), who were both quite drunk (there was free wine). They continually touched the artwork and made many obnoxious, incoherent sentences, while I tried to escape. I claimed I was going to show the girl around and eventually we ran into my sister. My sister lived in the city and we were planning on going to see a midnight showing at a movie theater together later that night, I would then spend the night at her apartment. While we were talking my sister asked if she was going to the movie with us, the girl then asked her mom if she could and surprisingly to my dismay she said yes. Remember, this was the first time she had ever met me. This cut off all means of escape. My parents were pissed at me because they thought I had orchestrated the entire thing, which made a very awkward family dinner. We went to the movie and she kept asking questions the entire time- the only thing that can kill the brilliance of A Clockwork Orange. Eventually we got home to my sister's apartment at around 3:30 or so and she went to sleep, no goodnight kiss or anything. I ended up spending around 20$ for tickets and popcorn, and 10$ for makeup remover because apparently she used up all of my sisters. I was very relieved when her mom picked her up the next day around noon. I even pretended to sleep in so I wouldn't have to talk to her the next day. The strange thing is that she called me while I was writing this.

Ryan / December 14, 2008 11:04 PM

So, my worst date is more just very awkward. I was invited to go hang out with this girl and her friend. She was trying to set me up with her friend. So, I go and start hitting it off immediately with this girl's friend. We're having a good time and rocking out to the live music. We start dancing a little and some light kissing happens. At this point this guy (who's beend kind of hanging out behind us and talking to the other girls occasionally) comes up to us and starts yelling at her and flips out. Apparently he was also hanging out with those two girls and really liked her even though he didn't say a word the whole time I was there.

Well, she yells back and he stomps off like an 8 year old and storms out the bar. So I think to myself well that was an odd occurrence. But things get back on track, but she's still flustered and wants to leave, I agree to go back to her place. At this moment, I'm thinking that guy flipping out could have worked well in my advantage. I thought wrong. So, we leave the bar, catch a cab back to her place. So, we are literally on the doorstep of the house and she gets a call from the previous disrupter. He apologizes profusely and then she tells him to come over. I'm thinking what the hell is going on. So this kid shows up and she immediately starts blowing me off and by the end of the night she ends up taking this kid to bed with her. She lived no where near a metro station, so I was forced to sleep on her couch til the morning. Then, I had the extreme joy of the other kid coming out and giving me a gloating smile like he one a competition.

So, my date went from good, to fun, to interesting, to crazy, back to fun, to terribly awkward, to having to spend another 30 dollars on a cab and 45 minute cab/metro ride back to my house.

MJ / December 15, 2008 9:21 AM

OMG does the insanity ever end??? ASS is the word of the year.

Here's another for the dating manual... Last night (wednesday) I agree to meet a new man out for a drink (of course we met from that internet dating site.) So we decide on New Smyrna Beach... I'm looking all cute in my little denim skirt, black leggings, black top, killer heels! We meet at one place, but it's closed, so I suggest the Flagler Tavern. I've never been, but always wanted to go because it's got a cute front porch to sit outside. It was a beautiful night to sit outside. So we park our cars, we are walking in and he pats my bottom... biggie, wasn't expecting that, but I was ok with it. We walk in, talking, laughing evening going pretty good (it's only been 5 minutes so far). I start to walk toward the porch and he says he wants to sit inside ... biggie again... We get a table in a room with hardly any people and the waitress hands us the menus and goes about her way. So I ask him how is day was blah blah blah, yadda yadda ... We are making small talk over the next 5 minutes trying to decide what we want on the menu. he leans over and caresses my hand. So after another few minutes, I said, "I wonder where our waitress is". So he answers, "I don't know let me check"... He gets up and leaves the table... end of date.... WTF... lol

I see him walk out the door and I thought to myself..well maybe he forgot his wallet... then I see his car drive past the window where I was sitting... ATM??? lol So I text him and ask if he just reply. I call, no answer. So I text my bffgf and tell her. She texts back..."ASS". The waitress comes back and asks where he is, so I tell her and she called him several names (an ASS, a shit, a loser..and a couple others) and made me come out to the front porch (where I wanted to be originally anyway) and gets me a drink. So the bartender comes out and we were all discussing the events and he keeps trying to get me to take a picture of myself with my hand over my forhead with the LOSER symbol! I finally get a text back from the ASS... this is what he wrote, in all caps, "SORRY MAURA U AND I WEREN'T FEELING IT AND NO TO YOUR QUESTION (I had texted, do you do this to all your dates) BUT SHOULD HAVE ON MANY OF THEM. I KNOW U UNDERSTAND AND REMEMBER DONT GIVE UP, WE WILL BOTH FIND THE ONE BUT YOU CAN'T GIVE UP". So of course I sent one back "that was SO rude on so many levels. You don't leave a woman alone in a bar. You didn't even give the evening a chance at all. You will never find someone with the way you just treated me. No wonder you've never been married."

I know other people have had that happen, but I don't understand the logic in it. It's cowardly and extremely low class. I've been stood up in my past, but not AFTER we met and are about to order a drink! So to the staff of the Flagler Tavern ...THANK YOU. They took me under their wing like an injured bird and fed me liquids to keep me strong..( But what started out as a crappy evening, ended up quite fun and silly.

TMI / December 15, 2008 1:45 PM

I just have to say thankyou for helping me kill time!

About a year and a half ago I met up with this guy i had met thru a dating site. i wasnt all that into him to begin with but i figured id give it a chance, im optimistic. so im a tall girl about 5'9'' and i just cant do guys that are shorter then me, just not what im attracted to, he said he was 5'10'' or so.... i show up and hes maybe 5'6''. he comes up to give me a hug.. akward, im towering over him because im also wearing heels. not to build myself up or anything but i was just wayyyyy out of his league. hes a couple years older then me but going nowhere, his place was disgusting and had crap all over the place. i wanted to bail right then but i didnt want to be rude. i didnt try to lead him on or anything, stayed pretty distant kept trying the whole... "i have something to do later..." the whole night hes trying to tell me his whole sob style life story, just really really pathetic. he was creepy clingy the whole night. i finally get out of there and have never responded to the many many many texts phone calls emails etc that he has sent me. all of which talk about our amazing connection and how were so in tune with each other. the last text and then phone call i recieved was about a month ago. I answered the phone pretending to be some middle eastern woman (heavy accent) and told him he had the wrong number. (he still calls..)

TMI / December 15, 2008 1:49 PM

by the way, the dating sites are not all bad, i met my current boyfriend of 8 months on one and he is wonderful! so everyone hang in there

Tom / December 15, 2008 3:50 PM

I met this girl Salvadorian girl named Wendy on Myspace. We had been friends for a while, then one night she comes over and we're watching a movie and we start messing around.

We move to the bed and I start sucking on her titties. Then as she's playing with my member, and I'm trying to unzip her pants, she decides that it would "be awkward to cross the 'friends' line" - um hello, line already crossed!

Needless to say I didn't get to stick it in. HORRIBLE BLUE BALLING!!!

Cait / December 15, 2008 6:27 PM

My worst date (not really an official date, at least not to me, but I guess it counts) was in highschool. I was a freshman in the marching band and had been asked (by a female friend) to go to something called "Fifth Quarter" at a nearby church. It's no secret that I'm not a religious person, and she told me that it was basically just a party that people went to after the games. So I agreed to go. Later on in the week, this junior guy who studied guitar from the same person I did (he told me later that after hearing me play at a group session, he was enamoured or something) randomly came up to me in the hall after one of my classes and asked me if I would go with him. I told him I would be there as I was going with a friend. So I thought that was the end of it. After the game that week, I showed up and of course, he was there. The big "activity" was a giant maze made out of cardboard boxes in a giant room with the lights turned off. You had to find the end where there was a flashlight set up or something. ("Seeing the light" can see where this is going.) So I spent the entire night in a hot, sweaty, cardboard box with someone's ass constantly in front of me. To top it off, as I was getting ready to leave with friends, he followed me and said " about a kiss?" (trying to sound really smooth) I was completely taken aback since I didn't even know the guy. The most I could manage to say was "Erm. How about a hug instead?" so I gave him one of those really distant pat-on-the-back hugs and got away as soon as possible. Um. Awkward anyone?

Sarah / December 15, 2008 6:44 PM

These are some pretty fun dates.

My worst date.. I suppose... wasn't technically a date.

One of my girlfriends and I decided to go out, she was upset because her boyfriend and her were in an argument, and to top it off she thought she was pregnant with his kid.

We were going to go shopping and then out to a bar to spend some girl time together, but when we went shopping we met up with a couple of guys from the Marines who asked us to a party they were having. We decided to hang out with them, ended up going to a strip club, and soon my friend was shoving her tongue down one of the Marine's throats. I just kind of sat around with the other guy making awkward conversation (he had a fiancee). We ended up following them to one of the guys' houses.. and they got lost on the way there, so I wasted an hour and gas just following them. We go to the guy's house and it reeks of cat piss, and he lives in his mother's attic apparently. After less than a half hour I pry my friend off of her soldier-boy.

When I finally found my way back to town my friend and I decided to stop by a party at my sort-of-boyfriend's house. We all have a blast, making tons of new friends.. but everyone was hitting on my friend which was getting on my nerves. My friend and the guy I had been seeing mysteriously disappear down the hall.. chatting it up, and later I find them getting cozy on the tailgate of someone's truck outside. I called him out on it when they came back inside, and he started yelling saying that he wants to nail my friend and that I shouldn't have any problem with that.

I got out of there and left her there.. stayed the night at my friend's house and picked her up the next morning from my guy's.

*grumbles* I just LOVE humans.

TomSteele / December 16, 2008 12:52 PM

Never underestimate our own need to feel loved and wanted - and what that may do to our judgement. . . .

I went to visit my friend from high school who lived about 120 miles from my house. I was just out of high school and we had not seen each other for a good while. He had moved a few years earlier, and had a crowd he hung out with in Fresno.

When I get to his house he asks we catch up and he lets me know we will be going out drinking with some of his friends later that night.

Later we drive to this very nice apartment complex and crowd into a nice apartment with about 20 people laughing and having drinks. It seemed very nice, civilized and low key.

I felt a little odd as I knew no one, and my friend was off mixing with his friends. But, I could have found myself in worse situations.

I am generally shy and do not approach girls. So I was not likely to fulfill my ongoing dream of making a connection.

To my amazement, I kept noticing that a very nice looking , dark haired girl kept staring at me from where she was sitting on a couch. I pretended not to notice for awhile, but then she starting smiling when I looked her way. I did not have the social capacity to approach her.

She however, got up after about 10 minutes and made her way to me. We made some small talk and she really seemed to like me! She asked if I would like another drink and suggested we go out on the balcony, since it was Summer, and a very nice evening.

I watched her walk over to get us fresh drinks, and she looked very nice. We then walked out to the balcony.

We commented on how nice the evening was and then she abruptly stands back a few feet and asks me how she "looks". She had very tight pants, and a very tight top with apparently no bra on.

I was a little dumbfounded, but was able to stammer "great". She smiled and came back closer to me. I was feeling like I was somehow transported to a universe where this sort of thing actually happened to me!

Ti my utter astonishment, she then cupped her breasts in her hands and said "see these"?

Before I could answer with my non-functioning dry mouth, she gave her own comment. "These are for Jesus".

My mind began folding back into itself like some type of 60's LSD dramatization as I tried to process that. I didn't, couldn't say anything to that, so I just looked at her.

Then I said something that didn't turn out to fit her script. . . I told her boldly "I am Jesus".

Her face scrunched up and she began to cry - then she started yelling loudly "Liar, LIAR!".

The girl whose apartment it was came out quickly, with my friend and they asked what the hell was going on? The police would come, could "we" please stop it.

I was speechless and my previous Goddess responded by falling to her knees and projectile vomiting onto my lower legs and shoes.

My friend looked at me quizzically as if I had somehow planned this, and the apartment girl asked me NOT to come inside. She brought a pitcher of water and doused my legs 3 times without even asking. Then she said "go".

The previous Goddess was being administered to by her friends who had come, and they also shooting me dirty looks.

The Goddesss came back to life and started crying "Danny", "Danny" (not my name). Her friends hauled her out and they took off.

My friend told me to wait outside and he come in a few and drive me back to his place. I waited with wet legs for 45 mintues. Then he came and we drove back to his place without a word.

Kate / December 16, 2008 3:40 PM

I've never really had a bad date, up to a few weeks ago. I met this guy at work; we spoke a few times, he seemed a bit shy (Not really my type - I'm shy too, and it just makes things awkward), but otherwise nice. He asked for my number, and I gave it to him.

I should, in hindsight, have seen the warning signs in the phone call. He called me a few days later, and one of the first things he asks me is 'what's the longest relationship you've been in?'. I'm an shy, introverted 18 year old, and even my claimed 'about a month?' is an exaggeration. He seems to have a bit of a problem with that, and proceeds to question me on exactly WHY I haven't had a longer relationship before, which is uncomfortable to say the least.

He later goes on to talk about his last girlfriend, and how he broke up with her because they'd drifted apart and she was interested in someone else. Er, right, oooook... So, did I think he'd made the right decision in letting her go? Er, excuse me,what?

For some reason, I agree to go on a date with him, and we end up seeing James Bond at the cinema. The date isn't bad, except that he constantly asks me 'are you ok?' as if I'm about to drop down dead, and gives compliments in a very odd way. He also feels the need to ask if I have a problem with 'people of colour' - I clearly knew he was black when I went out with him, so...necessary to ask?

I'm not so keen, we don't have much in common. He also made it extremely clear on the phone that he was not looking for a very serious relationship, as he didn't have a lot of time with his university and job. That was cool with me, I just wanted someone to meet up with every so often.

He texts me a few days later asking when he's going to see my 'pretty face' again, laying it on a bit thick, and I don't bother replying.

He calls me the next day and I don't answer. He then texts me saying can I please reply, because 'I'm worried sick, i couldn't even sleep last night'.

Keep in mind we'd only properly met ONCE.

That pretty much freaked me out, so I made up some excuse about getting with some other guy and sorry bs, and luckily I haven't seen him at work since.

I did, however, later find out from a co-worker that he is ultra-religious (I'm athiest) and a bit of an ass. Working in a mental home, he told a lesbian patient that she would 'go to hell' for her homosexuality, and another self-harming female patient that she 'has a mostache' (she then went out and burnt herself with a cigarette).

anon / December 16, 2008 10:47 PM

Two years after high school my buddy rented 2 adjacent rooms at a motel for a new years party. It got a bit wild so we decided we should leave the hotel and go to another party. Got to the party, lots of people who I went to high school with, but didn't really know many. They were all a year younger than me, and all in the pretty/popular clique. A few hours in, I started talking to, and hitting it off with, a girl (girl 1)I had met at a previous party. She was friends with my friends and things were looking good for me. On my way to the bathroom I started talking to another girl (girl 2) who I had always thought was a stuck up bitch, but never really knew. Being a bit drunk, I proceeded to tell her what a bitch I thought she was in high school. Next thing I know, she's hitting on me hardcore and wants to leave with me (this was the first time i had ever been an unjustified asshole to a random girl, and it fucking worked.. wtf) Next thing I know, I'm in a backseat with both of them and a buddy, with my other buddy and his gf driving us all back to our motel rooms. The ride was both awkward and exciting in a way. Girl 2 must have been pretty tipsy because she decided to sit on my lap in the car (4 people in the back seat). She kept rubbing on me and leaned back, and put my hand up her shirt. At this point I didn't really care about girl 1 anymore. Frankly, I'm surprised she came along. Anyway, we got to the motel and all had a few more beers. I guess Girl 1 came to her senses, because she asked me to drive her home. I though oh well, I still have girl 2 when i get back. We pull up to her house and she starts to get out (i dont even try to walk her to her door, at this point ive given up on her and can only think of getting back to girl 2 before she passes out). Then, for some reason she invites me in, but in my drunkenness I don't put 2 and 2 together quick enough and tell her im tired and gotta go. I RUSH back to the motel to find my buddy in bed with girl 2 and I slept in a bed in the same room with them listening to them fuck all night.
Though I secretly resented my buddy at first, I didn't give him any shit for it. I would have done the same thing.

dz / December 16, 2008 11:30 PM

Dude Wolfman BEan,
You win

Raul / December 17, 2008 12:45 AM

while the date in particular i am going to mention was not an overtly bad date, it did involve the most frightening moment i have ever had involving a girl.

Her name was Cassandra, and I, your humble narator met her through a mutual friend while working at an amusement park over the summer. Riding rides with Cassandra and Michelle (the mutual friend) and their group of assorted 18-19 year old girls after i got off of work for the day was wonderful. Cassandra and i hit it off splendedly and texted eachother constantly over the next few weeks. A few weeks later i had a saturday off, which was also her day off her equaly demanding job (we both worked 60+ hours a week, which would ultimately spell the downfall of this otherwise nice relationship), so, i spent the night.
her mother was out of town that night (we both being 19 at the time) and she and i had a wonderful night. however, she gave me the fright of my life: while straddling me from behind and giving me a quite wonderful back rub, she uttered the fateful comment "i cant wait untill you meet my kids".

needless to say i almost shit myself in a blind panic that lasted a full 30 seconds. She spent the next 10 minutes profusely explaining that it was a joke and attempting to allay my fears.

She honestly was joking, but it freaked the living shit out of me.

Now, the worst date i had ever been on again involved Cassandra, and her friend Tanya. They came to the amusement park where i was (still) working that very same summer. after i got off my shift i came and hung out with them. Tanya had to be the most annoying insipid and dumb girl i had ever set eyes on(too bad she was the best friend of the girl i was sleeping with). Now, as one can imagine this quickly turning into a clusterfuck. It didnt end well.
I did not like Tanya, and i, being a polite person, did my absolute best to be a perfect gentlemen to her. This did not fool Cassandra. Her feminine radar for chickannery went berserk and she quickly became angry at me for not liking her best friend. At this juncture i also want to note that if i did hit it off with Tanya, Cassandra would have become jealous and would have been equally angry at me for not paying as much attention to herself as she had wished.
talk about a catch 22.
it sucked, a lot.

michelle / December 17, 2008 7:31 AM

my first date was with a guy i met at school i was thrilled because this was my first real date. i never had one in high school or even after high school it took 2 years to get one and it only took two hours and 40 secounds for him to ruin it.. he stood me up i sat there in my nicest clothing i own waiting. what made it worse was my mom sitting in the car waiting to see him and nothing... he never shows..
two hours later i left then another 2 hours went by before he called me.
i'm glade we didn't date tho found out he had slept with this evil girl from my work..

AwesomeDannyT / December 17, 2008 1:18 PM

ADT’s The Worst Date Ever (Written 16/03/08 Happened 2004)

This is another story that happened years ago. I have learnt a lot from past dates, this is the strangest, and most weird I have ever been on by far. I have spoken to lots of women since about “if this was normal” and it appears it definitely is not. It scared me at the time and to this day, but decide for yourself.

I will call her CurtainGirl; this will become obvious why later on, but for now just roll with it. So I had got with a girl in the local club couple times. Seemed fairly attractive and intelligent when I had spoke with her. Although since I have realised anyone you talk to when both of you are hammered in-between fumbling around on the dance floor probably will not meet any remembered expectations in the conversations department. At this period in my life I honestly thought being “nice” and dating a girl many times was the only way to hook up. Surprises even me how naïve I was going back only a few years. If I could go back in time I would slap myself a lot for being so retarded.

It took me a lot of balls to ask CurtainGirl out, I was a late starter in my dating life and it was certainly always a big step for me, but I thought if this girl kisses me she must “really like me”(Fucking duh!). So I saw her out a few weeks later in the normal slut rags and 10 layers of make up that most teenage slags wear and after buying her a few drink and a couple more kisses I finally did it:

“Do you wanna grab a…. Drink…. Or some food or umm something sometime???”
Dam I sounded like a dick. She was and still is a blatant hussy, how I could not see it I do not know. I could have told her to suck me off for fiver and she probably would have pulled out some “buy one get one free” vouchers from between her flaps.

I can’t remember what CurtainGirl said, but it must have been good as we went out about a week later. I got all dressed up to take her for a drink, borrowed my mum’s car as mine would break at least every other mile back in the day and headed over to pick her up. I was shitting it. She climbs in, dressed in another tiny skirt, push up bra and make up so thick it you could ricochet bullets off. My small talk sucked, but she didn’t seem to mind too such, we went to a bar just round the corner and swigged one down in virtual silence, completely reinforcing my point, if your both drunk, talking really doesn’t matter! One of the most uncomfortable feelings I thought I could experience just sitting there in the quiet, well that’s until we got back to hers.

We leave and head to her house. CurtainGirl lived with her mum in a run down bit of town. Mum was out for the night (probably satisfying her latest trick, but I didn’t ask). We opened a cheap bottle of wine, and she leads me upstairs by the hand. Now I am nervous, getting lucky on a first date, pro I think. I was not a pro.

She takes me to her room and CurtainGirl leaves me sitting on her bed while she uses the bathroom. Now I know that some girls like to do “something” in there before going any further, but what followed was not expected.

Out she comes, but not in the slut rags which I was enjoying the occasional sneaky revealing glance, and not even in something more bedroom like, No. She comes out in green pyjamas. When I say green pyjamas I am not talking cute ones with cartoon characters on, not at all, I mean library curtains from the 1970s. Stripy, mouldy green pyjamas. Way to turn a guy off. But this was not all. She had also removed the kilo of make up (I am guessing with a blowtorch or similar device).

CurtainGirl is no longer the quite attractive girl she was before, far from it. Now I want to burn my eyes out with a smoke stick. Why did I decide to drive tonight? I think to myself. I could handle this drunk just fine by either passing out or selective glances and ignorance. Don’t get wrong most people, girls especially feel very comfortable around me but this was too much. It was the first date for fuck sake.

BUT then, as if I honestly thought it couldn’t become anymore fucked up… CurtainGirl reaches beneath her bed pulling a pink shoe box from under it. I am thinking maybe its secret booze stash, condoms or an excuse to get on her knees for my pleasure. I am not so lucky. She opens the box to reveal a full collection of at least 20 dildos and vibrators. Every size shape or colour I could imagine was in there. I had only been with half a dozen people by this age so not even seen them before much at all. Now, I have no problems with toys at all, (in fact I fully support the use, regularly) but is a first date really the place for them? I think not.

You might think I powered through the questionable dress sense, lack of attractiveness following make up removal and this large box of battery operated nympho kit to leave the next day barely able to walk and a fully qualified porn star. No, this was not the case; I could not look CurtainGirl in the eye following this and have no idea of any of the conversations that followed except:

“Well thanks for a great night, but I got a meeting in 8 hours, (yawns) I really should go”

Yes I was pussy, but fuck it. I mean if a girl wants to lure a guy into her bed don’t do the above. ANY OF IT.

Please visit my site for more embarrassing and revealing true stories from my life! lol.

dvlcis / December 17, 2008 2:41 PM

wolfmanBEan, you should be writing books. great literature. and somehow I envy you this date. life's just so short... ;)

Matt / December 17, 2008 3:00 PM

She was fat.

Andrew / December 17, 2008 5:01 PM

Welcome StumbleUpon readers!

While you're here, you may wish to explore the rest of Gapers Block. We promise, it's worth your while!

john Tommervik / December 17, 2008 6:33 PM

HAHA.... these bad dates are hillarious!i

I think the guy in this video had one of the worst first dates. lol

sinbeautybliss / December 23, 2008 2:31 AM

My worst date was with my long term boyfriend my senior year of high school. Prom...of course.

My high school only had one formal homecoming or any of that so I was really excited about senior prom. My boyfriend and I had been dating almost a year at this point and I was thrilled to have a special date night. You know...getting dressed up, make up done, all that. Junior prom I wasn't as into it...nice dress, mom did my hair and make up, real simply. So senior year I had this dress that I felt incredibly sexy in, my boyfriend adored the color and couldn't keep his eyes off of me, I actually had my make up done and my mom spent two hours on my hair. But our plans were awful.

We went with a group of friends (really more his than mine but at the time we hung out a lot) all of whom were not really up for the whole prom thing. The only other "couple" was not actually dating at the time. One of the others' boyfriend was in basic training at the time so she took another girl we were friends with but didn't go to our school. Since none of them really cared we skipped the whole limo thing and decided we'd drive our own cars...meaning I had to drive because my boyfriend didn't feel like it. Again, at the decision of others (which I objected to in private...many times) we went to TACO BELL in our dresses and tuxes for dinner before prom...where I payed. (Did I mention I also paid the $80 for our prom tickets?).

When we finally get to prom we had to take the official pictures ('s part of the event) which we decided we wanted some prints of...I wrote a check. We went into the dance area which was nice but the theme was "a night of elegance" and I could not get over the redundancy of it's prom. Anyway, we find a table to put our things down and sit. After begging for ten minutes I finally convince my boyfriend to join me on the dance floor where he just stands looking entirely put-off by having to be with me (mind you, he's already graduated...but he felt he should count this as his senior prom too since he skipped his). After the first slow song he sees someone he wants to say hi too and wanders off.

I decide to find some other friends since no one in the group I came with wants to dance or even have a good time. My boyfriend seems to only appear for the slow songs...and if I sit down to take a break. Numerous times throughout the night he completely disappeared (turns out he was trying to smoke a joint with the other guy in our group...both non-students and therefore our guests...our responsibility.)

At about 1130 we decided to leave (prom ended at 12 anyway...) because we had plans to see a show. All of a sudden my boyfriend has disappeared...and one of my favorite dance songs had come one (get low...what can I say it's fun to dance to!). Turns out he and one of the other girls in our group were dancing to it with some other friends. Whatever. We walk back to our cars and he decides he wants to ride to the club with the other guy, so the girl rides with me. It's only a ten minute drive so whatever. We get there and the boys are no where to be found. After waiting in the parking lot for fifteen minutes we decide to go into the show without them (this, of course, was the only part of the night he was planning on paying for and he was no where to be found).

We found really great spots near the stage, even though we got there with only an hour left of the show. This was the best part of my night! As the band was starting their last song the two boys finally show up. Turns out they smoked a bowl then turned the wrong way down a one-way street coming out of the parking garage, THEN got lost on the straight shot to the show (literally, had to go up a block, turn left, go straight) and had to smoke another bowl before coming in. The show ended and we left the rest of the group and went back to my boyfriend's house where I passed out, exhausted and pissed off. He never understood why I never got over that night...

It took me a year after that to dump him...stupid.

Elizabeth / December 25, 2008 10:01 PM

I'd been talking to this guy for awhile, via e-mail, and we finally decided to meet and go out. We decided on dinner and a movie ahead of time.

We arrived at the movie theater, and he immediately insists on seeing Jack Ass II. I didn't want to see it, and told him as much, but he said since he was buying the tickets, it was only fair if he got to pick out the movie. I thought he was being kind of a jerk about it, but I could see some logic in his reasoning, so I agreed.

During the movie, he repeatedly tried to hold my hand. Normally, I would've been okay with that, but it's kind of disconcerting to hold hands with someone who's laughing REALLY, REALLY loudly at stupid people hurting themselves. So I kept pulling my hand away, and finally clasped my hands together so they wouldn't be available for grabs. But evidently, when a girl doesn't want to hold a guy's hand, he thinks that means he should touch her knee, and then upper leg. I was completely and totally uncomfortable, but he was my ride, and I didn't know anyone with a car who wasn't over an hour away at the time. So I endured it.

Afterwards, he took me out to "dinner"... at Chic Fil A. For two college kids, that's not a bad dinner, I guess. But it really showed me that he didn't pay attention to much of what I'd told him during our online conversations. I know for a fact that I complained about eating Chic Fil A multiple times to him. At the time, it was the only thing on campus that I ever really ate. So if I was going to get the chance to eat a meal off campus, I never, ever, ever would have chosen Chic Fil A. But he was paying, so I held my tongue.

During the meal, he kept talking about how all the girls who knew him wanted to date or at least have sex with him, and all of the guys were so jealous of him. That's seriously ALL he talked about. It was so annoying that I finally cut the night short... I feigned stomach pain, had my sandwich packed to go, and asked him to take me back to my dorm.

All the way there, he kept trying to get me to take pills. First, he said they were something to help my nausea. I said I was also really tired, so the best thing for me would probably be rest. Then he said that the pills were actually caffeine pills, and they'd help me stay awake. I declined. When he got me back on campus, he asked if he could come inside my dorm room, and got really pissed when I said it was against the rules. He called me a tease, and asked me not to contact him again. And guess who texted me the very next day to see if I was available to hang out the following weekend? Oh yeah. I wasn't available ever again.

Lehrin / January 4, 2009 11:24 PM

A girl came up to me while I was studying Organic Chemistry in a coffee shop. She asked me some Chemistry question that I don't remember, but it was clear that she had only asked in order to have an excuse to talk to me. She didn't have a phone at the time so we coordinated our date by email. I went to her dorm room/apt. to pick her up, after just finishing a very intense track workout and I was exhausted... so a girl answers the door and she looks familiar, so I ask her, "You look familiar, have I met you before?" She asks, "Who are you here to see?" I say, "Shannon." She replies, "...That's me."
We didn't go out again.

Paper Doll / February 6, 2009 10:38 PM

I'm going to have to go with the one who, while hooking up, decided a pocket knife was the perfect accessory to fellatio and chose to pull one out on me... all in reference to a joke made HOURS before.

Jade / March 17, 2009 9:10 PM

Here is a story about my friend. That was her worst date. So her boyfriend and she went to the park after the café. Everything seemed alright. And the girl was in love and happy. The guy was rude and self-confident. She got used to it. So they were walking, having a kind of talk and then he asked her to wait a little – a call of nature.
She was waiting for him nearly half an hour or even more…and then it turned out – he was arrested for pissing in a place he mustn`t

Loralei / April 2, 2009 1:38 AM

About 5 years ago, when I was 20, I met a guy online. I knew he was older than I was, but he said 28. He sent a pic, but as I found out, it was of him when he WAS 28, and he admits that he is now 47 (obviously).

So being a nice person, I have no clue how to just leave, so I figure I'll go in and have dinner. We eat, and the whole time he's throwing compliments around, which are weird to take since he's almost as old as my father (creeeepy).

So we finally get done eating and listening to his stories about his recent divorce. I had driven myself thank god, but he says he has something for me in his car. In his trunk he had 2 bouquets of flowers, 5 packs of incense (wtf?), a lot of little boxes of chocolates, and a hue bag of peanut M&M's. Mind you I had never said anything about any of these random things.

So I get the hell out of there, he calls me at least once every day and leaves voicemails about how he felt "a connection". Then 2 weeks later I receive a package taped to my apartment door (I never told him where I lived). It was a religious DVD about how homosexuals go to hell (we had discussed online before we met that my father is gay). Then he incessantly instant messaged me about to see if I had received his "gift".

Needless to say it took multiple threats of notifying the police before he quit leaving me religious and edible tokens of his love.

Thank god I'm married someone else!

cs / April 5, 2009 9:35 PM

I went out with one of my coworkers who grew up in a log cabin with his seven brothers and sisters in the middle of nowhere. He: religious, sheltered under patriarchy, and socially awkward. Me: the opposite. But he was cute and very nice, so I thought I'd give it a whirl.

Things started to go south when:

He drove under 20 miles per hour the entire trip from my house to the Chinese restaurant.

In silence.

He'd never been to a Chinese restaurant before.

He ordered my food for me.

He wouldn't split the bill with me.

Very nice guy, though, just not for me, thus making it the worst, or maybe most awkward date I've ever been on.

Aquagirl / October 7, 2010 7:21 PM

I met a guy online who claimed to be a high profile actor that could not reveal his name over the internet. Ok, sounds intriguing, although I'm not the type to be starstruck he said he wanted to meet and I agreed to it.

I arrived before him (so I thought) at the restaurant he wanted to go to in Beverly Hills. I sat down and waited for a few moments and the "manager" of the restaurant asked me if I was waiting for "Brett Champion"...I said yes. He ushered me to a private room while I waited for another 10 minutes and then the manager asked me to come into the dining room. He sat me at a table and Mr. Wonderful walked in and joined me. I assume he thought I was blind because although he claimed to be 6'3", I was taller than he was at 5'3". Anyway, pretty immediately girls started coming over to our table to ask for his autograph. One after another they kept on coming and drooling all over him and I still had no clue who this guy was. Then the wait staff began doing the same thing. He said it happened constantly and thought he would be able to enjoy a peaceful meal here but it was almost impossible anymore. About an hour into seriously boring, bragging, and conversation I got up to use the ladies room and while I was in there I could hear two women talking about making $10.00 to ask some guy for his autograph. This freak actually paid about twenty different people to do this. Ekkk.

I returned to my seat to find him suddenly VERY DRUNK. He got down on the floor and laid his head in my lap and asked me to marry him!! I quickly pushed him away and said I needed to leave. He wanted me to meet him at this other "exclusive" club for some dancing. I said sure, and got directly on the freeway and went home.

A few weeks later I am watching television and there he was on DATELINE NBC. He was being interviewed and told the interviewer that as a part of his parole after being in prison for conning many women out of money, the judge ordered him to do interviews and write books warning women and showing them how NOT to get conned. (That was also a con)

About a week after that, HIS WIFE called me and asked if I would be willing to speak to the FBI about what he did since he was once again commiting fraud all over the place. I did and a few months later I heard he was back in prison....thank God.


Lea / September 18, 2011 5:26 PM

Cute guy. Knew him for awhile. Asked me out to dinner for a date. Great conversation. He ordered a lot of great food and told me to order whatever I like. Check came. He "forgot" his wallet.

talesofakat / September 25, 2012 9:44 PM

It was Valentine's Day with my boyfriend of a little over a year. We'd gone all out for Valentine's the year before, so decided to keep it low-key (and much less expensive) by cooking a nice meal together at home.

On the menu: prime rib steak, cheesy potatoes, fresh green beans and not-so-bad wine. It took us longer than expected to cook (neither he nor I are especially talented in that department), so by the time we lit the tea candles and plated the food, we were both starved.

We sat down to our little romantic dinner, clinked glasses and took a first (big, due to slight starvation) bite of steak. DELICIOUS, and perfectly done. I look up from my enjoyment of the meal to see how Dylan is doing, to see a slightly pained look on his face. He reaches for his glass, and takes a big gulp, and I'm thinking, "Well I thought it was good! And usually anything red meat is a win in his book."

His pained look gets worse, and I'm wondering how in the world I managed to ruin his steak but not mine, when suddenly he leaps out of his chair and heads toward the kitchen sink, spewing wine everywhere.

I'm just staring, stunned, when he turns around with the universal "I'm choking. Save me!" hand signals at his neck.

I jump for him, wondering how in the hell I (a slightly short, 5'4" 115 lb. girl) am going to give the heimlich maneuver to my 6'4", 200+ lb. well-built boyfriend. Also, did I mention I'd only ever seen this done in movies?

Well, panic can do funny things to a person, because I lifted him clear off his feet. Two tries, and a half-chewed piece of steak flies out.

Dylan wasn't much for finishing the meal after that, but I guess saving his life made the evening a win anyway.

Also, he now chews his food much more carefully.

CandyWife / September 27, 2012 3:20 PM

This actually happened to my husband before we started dating. He had just gotten out of a relationship and decided to take this girl to a concert. The whole time he was protecting her from people in the mosh pit and making sure she was taken care of the entire time. She then excuses herself to go to the bathroom. A few hours after going to the "bathroom" after the concert had ended, she ran up to him, looking disheveled followed by the guitar player of one the shitty opening bands. It was obvious what they had been doing. My husband was disgusted, and the guitar player had the gall to try and give him a high five and "say no hard feelings bro!" fast forward five years. We are married and in a different state attending a concert with my 14 year old sister. The same guy, now in another band, was there. He called my sister back stage and had her rub his shoulders, all the while he was caressing her legs. When he stood up, he asked her if she f*cked. She told him no, and that she was 14. He told her he didnt mind and that it made it a little more "bad". After the show he tried to get her to follow him but she blew his sleazy ass off. What a creepy jerk! We didnt even realize it was the same guy until afterwards.

VIrginia / November 27, 2012 11:32 PM

One of a thousand with the same guy: My ex-boyfriend asks me out to lunch one day. It's all well and good, we ended on a nice note because I was moving and we didn't want to do long distance...I didn't move... and we began dating again. So, we are sitting at lunch just beginning to eat. Literally, the food had just gotten to our table, when he proceeds to ask me, "Do you think you would ever marry me?" To which I answered honestly, "No, we break up and get back together too much. We fight. We are opposites on everything and you're a flirt. You're a great date and I care about you, but as for long-term commitment? I don't think we will be together forever or more than friends. I am just enjoying the moment and the time we spend together." Harsh? I know maybe a little, but seriously? You're my ex-boyfriend! Who broke up with me! And this is a casual lunch date.
His response:
without touching his food he gets up and leaves. Deserting me at Corner Bakery Cafe. I waited for 10 minutes, thinking, we've fought badly before and he came back after a little while. Well, he didn't come back. I proceeded to eat my lunch....AND his. Then I walked home.
(Yes, he called later to lecture me on being rude and unromantic...lecture me).

Anthony / December 23, 2013 2:42 PM

There was this girl that I really liked. We were friends, and she told me that she didn't feel the same way. So I went on with my life. Then, she wanted me to ask her out. I was very confused but I did so anyway. We were supposed to enjoy a lunch on the beach. When I picked her up, I learned that she already ate lunch. A storm then broke out. The date was ruined and we spent the day driving around in near silence. It was terribly awkward. The worst part is that she blamed the whole thing on me.

bucklaw / December 31, 2013 3:49 PM

A woman at work was selling tickets to a local show, Jesus Christ Superstar.

Speaking out loud instead of to myself, I stated, "That would be nice," and as I said this I looked at the girl working in the office with me. Well the girl took it as an invitation and I ended up getting two tickets. She picks me up, states that she knows the directions and wouldn't listen to commonsense. It is a small town and this is the event of the night, so it was obvious where the show was. We get to intermission, she goes to sit in the movie theater chair and it breaks. All I could say is, "They don't make chairs like they used to." Nice person, looks deplorable and overweight. The accidental date.

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