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« Thanksgiving Reads: Hope Dies Last: The Lasting Scars of Difficult Times Moments of Possibility - An Interview with Dave Murray »

Dating Wed Nov 23 2011

Chicago Dating 2.011: The Best of the Worst

Previous Entry: The THIRD Date
Next Entry: To Be Normal

I have to admit that I've never really had a terrible, awful, make me reconsider the spinster lifestyle, kind of least on I've had awkward dates, I've had ugly dates, I've had dates I just wish would end so I could put on my sweats and watch Parks and Rec. But I've never had one of those truly terrible dates that you always fear when joining an online dating site.

For the most part I've found that my Match dates, if nothing else, have tried. They are on Match to date and therefore put a bit of effort into being entertaining or at least inoffensive. Even when I knew in the first two minutes that this would be our only date, I still usually had some genuinely enjoyable conversations. And even though three first dates a week can get exhausting, I generally still felt like humanity was good by Friday.

But despite my relative luck, I have heard some online horror stories from friends, dates and readers. With their permission and often blessing, I'm going to regale some of you with some terrifyingly real stories. Coincidentally, all of these happen to be first dates, which, for obvious reasons, were not followed by a second date. I hope the sharing of these experiences is cathartic and healing for anyone who has ever had a terrible date.

1. After rescheduling a first date three times, Goldy Locks (code name to be evident soon enough) finally met up with her much-anticipated date at the local Starbucks. Although sparks did not immediately fly, Goldy Locks kept an open mind even after Prince Charming rubbed her hand within five minutes of sitting down, noting that her hands "looked warm." Unfortunately the unnecessary and awkward touching did not stop there. There were three separate occasions of hair stroking, each preceded by some sort of uncomfortable compliment ranging from harmless, "I love your Jewish curls," to creepy, "You're hair is like a lion's. Are you a lioness?" (The response to this was no a simple "No I am not a lioness," to which the retort was "Well are you a tiger? Are you a tigress?") Although there was some lovely conversation about bedding and Jewish grandmothers, the hair petting quickly got out of hand before the coffee even cooled. As Goldy Locks puts it, "This is why first dates are in public."

2. Like any good oenophile (lover of wine), the victim in this story took his first date to Webster's Wine Bar to impress her with his vast knowledge of vintages. Unfortunately, Oenophile's date seemed to have a bit of a small bladder problem and seemed to visit the ladies room about every 40 minutes. However she came back from each visit with a seemingly boundless amount of enthusiasm and energy, almost an unnerving amount that was quite mysterious. The mystery was soon solved when she returned from her fourth trip with a bit of white powder under her nose. Gentleman Oenophile quietly noted she had a bit of left over under her nostrils and called for the check.

3. Our Online Veteran in this little ditty thought he had seen it all until a recent online date with a lady he met online. The initial plan involved drinks out but the destination was changed last minute to the lady's work party. Not only did our Veteran meet all of this new lady's coworkers (who were significantly more charming than lady friend) but he also learned that she had quite an affinity for alcoholic beverages. Having downed enough liquor to make Charlie Sheen seem sober, Ms. Tipsy decided it was time to go home. After our heroic Veteran helped her up the stairs, she made a beeline for the bathroom where, with the door still open, she proceeded to vomit up all of the night's entertainment. Veteran bid the lady a good night and made the most graceful exit possible.

4. Miss Congeniality was thrilled when her online date offered to buy tickets for Wicked for their first date. Because of his generosity, she offered to pay for dinner at a local diner. Her suitor showed up in a leg cast and about 30 more pounds than expected. He then ordered three separate entrees for dinner, none of which he needed a doggy bag for. Over dinner he explained that his injured leg had kept him inactive and he therefore had put on a "little" weight. After paying the surprisingly expensive dinner bill, Miss Congeniality and her date headed to Wicked, where she discovered, Mr. Big Appetite was also inflicted the most annoying of theatergoer problems. He was a distractingly loud breather. Heeehaawheeehaaaaw. After an agonizing night, Miss Congeniality drove her injured little bird home, speeding away before the subject of a second date could even be hinted at.

5. Although I don't think this really qualifies as a date (except maybe in the Craigslist personal world), if you are looking for one of the worst hook-up stories, this is for you. I'm not going to post the details because I do not wish to violate reader's fragile unadulterated minds, but feel free to check out the link. Also, shout-out to Reggie for this being our first communication in years. Way to keep it classy man ;)

If you are particularly bored on this Thanksgiving and wish to be entertained by others' misery, check out these sites for some more bad date stores: My Very Worst Date, A Bad Case of the Dates, and Marie Claire's Online Dating Stories.

As always if you have any qualms or quips feel free to email me at write2fritz (at) gmail (dot) com.


If you happen to be single during this most couple-y of times, just remember, count your lucky stars. Black Friday Shopping MN style.jpgAs a singleton, you do not have to deal with a partner's insane family drama, awkward familiar dynamics or cheesy traditions. You only have to deal with your own family's insanity and you can do that with a bottle of wine or conveniently hidden flask. 'Tis the season to embrace your own family dysfunction and be glad it is not yet doubled by a partner.

However, if you need a little break from all the holiday joy, there is always the Thanksgiving Day Parade tomorrow or the Music Box's Sound of Music Sing-A-Long on Friday. Also don't forget Black Friday is just around the corner. Better start sobering up now and don't forget your safety gear. (See picture for how we do Post-Thanksgiving Shopping in Minnesota). And if that doesn't put you in the holiday spirit, try listening to Mariah Carey's All I Want for Christmas is You on repeat. That seems to do the trick for me.

Previous Entry: The THIRD Date

Next Entry: To Be Normal

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Jess / November 25, 2011 3:12 PM

Since I have to be working on Black Friday, I am thrilled to have a new gem from your blog to read. Both amusing yet horrifying. Needless to say, I am now playing the Mariah Carey Christmas classic. Good call!

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Architecture Tue Nov 03 2015

Paul Goldberger Describes the "Pragmatism and Poetry" of Frank Gehry's Architecture in His New Book

By Nancy Bishop

Architecture critic Paul Goldberger talks about Frank Gehry's life and work in a new book.
Read this feature »

Steve at the Movies Fri Jan 01 2016

Best Feature Films & Documentaries of 2015

By Steve Prokopy

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