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Dating Thu Oct 20 2011

Chicago Dating 2.011: The First Date

Previous Entry: The Two Necessities for Online Dating: Courage and Chicken Wings
Next Entry: Match in the Midwest: The Art of Polite Judgement

Tuesday nights seem to be the official first date night and for good reason. Tuesdays are far removed from the wild and crazy jello shot potential of Thursday, Friday and Saturday. It is not Sunday, the day of god and hangovers. It does not carry the depressingly sober (or still hung-over) weight of Monday. It will never be suggestively referred to as hump day.

Tuesday holds the potential of the week within the safety of a normally boring day. And so the past five Tuesdays in my embarrassingly oversized agenda have become Match first date days.

Over the course of the past month and a half, the first date routine has taught me a bit about what it is like to be a semi-successful serial dater (defined by not being kicked out of any bars and occasionally scoring a second date). From my experience, I have gleaned a few words of wisdom for curious readers out there.

Disclaimer: Although inspired in part by true incidents, the following is fictional and does not depict any actual person or event. Any resemblance to real life is strictly proof of my lack of finesse as a writer. I mean really who would forget the name of their date? Fail.

-You should always schedule first dates for Tuesday nights. To do so by an actual telephone call is ballsy but risky as the phone call could take away all subject material for TBD Tuesday first date. Instead, rely on verbose texts which you will over-analyze down to the emoticon before sending. Resist the urge to text your best friend with said overanalyzed text to proof read.

-You should never ever ever meet for a concert, movie or other entertainment where you must sit or stand close to your date but not talk for hours. It WILL be awkward.

-You should meet for drinks or dinner but you should be absolutely 100% clear which you are meeting for. If you fail to define drink vs. dinner you could potentially end up either A) finding yourself eating a second dinner (Those bacon-wrapped dates will not look as tempting after you just finished your leftover lasagna. You will of course still attempt to eat and then spend the rest of the date wishing you were the kind of person who could throw up in a public restroom) or B)You will end up scarfing down a granola bar in the bathroom which is both unsanitary and weird. Note: Always bring a back-up granola bar if possible.

-Whether it is drinks or dinner you should eat/drink whatever you normally do...only cooler. Order that weird beer from Estonia or the appetizer you can't pronounce and pretend it is your normal routine. Eat/drink weird beer/appetizer even though it tastes horrendous.

- Try to act like a normal person even if your date is disproportionately hotter than you and you are having difficulties thinking coherently. Avoid thoughts such as "Shit they are way hotter than me. How the hell am I going to pull this off?"

-Try to act like a normal person even if you date is not as hot as those Match profile pictures may have suggested. Repeat "inner beauty, inner beauty" in your head a few times.

-Smile...a lot.

-Do not forget your date's name. This will be horribly embarrassing to both of you. If you do forget it is probably a one or two syllable name starting with an M or N. Try just humming mmmmnnnn until the name comes to you.

-Do not mix up your dates' histories. If you do say "Oh right sorry I confused you with my co-worker Mmmmmnnnnn. They are the one training for the Iditarod." Note: 73% of potential dates on are training for something.

-Do not have more than two drinks especially if they are IPA's. I know, I know, you are from Wisconsin; you can handle your beer. No you can't. You are and have always been a cheap date. Quit while you still can fake sober and hide your hideous Wisconsin accident, doncha know.

-Do no talk about your ex, not even if your date does first. Not even if you are just really good friends with your ex now. Not even if your ex is a complete jerk off who left you with $3,000 of debt and gonorrhea. Just don't.

-If you do mention your ex, laugh it off. Make a joke about breaking sacred first date rules and change the subject quickly preferably to something hilarious that shows you are a completely normal and stable individual who would never stalk unfortunately-mentioned ex on social media. Or talk about sports. That seems to work.

-If they mention their ex laugh and jokingly note they broke a cardinal rule but since they are just so darn cute you can over look it. Pray they get the fucking hint and stop talking about how their ex screwed them over but they are totally over it.

-If you have any deal breakers, sneak them in. Mention your die hard love for the Packers and see if there is any murderous rage in their eyes. Make sure to have some Rodgers stats on hand in case you need backup. Ask for their thoughts on Kayne West. Run if there is excessive defense of the overrated, self righteous ass. Ask for their opinion on jeggings, hair pumps, and American Apparel. Ask for the check immediately if you get an affirmative on any of these. Against popular belief sneak in a political affiliation test by asking their opinion of the electoral college, how many Rush Limbaugh books they own or what they think of these soulless blood sucking Republicans.

-Try to not get into a loud argument, even if it is just a silly debate about whether sociology or political science is a more worthy PhD pursuit. (Spoiler alert: the winner is neither.) This is less because you don't want to offend your date and more because you would like to visit unspecified venue again.

-Wear comfortable clothes but put in some effort. We are talking a step up from your sweats with the hole in the crotch but leave the shiny Ed Hardy T-Shirts and pumps at home. Wear comfortable underwear understanding that no one will be seeing them tonight.

-Do not let anyone see your underwear.

-Have an out. Build in an end time or an escape route in case you are miserable and can't stand another awkward moment. If you don't, I suggest saying this but in a nicer way "I really cannot justify wasting one more minute of my life on this date with you. Thanks for the drink. Cheers."

-If the date did not go well and you feel the need to tell your date this, in the spirit of being honest and not delaying the inevitable, mention this approximately 30 seconds before you depart, not 3 blocks before you finally part ways on your separate modes of public transportation. You will never be so happy to see the Ashland bus.

-Do not ask what went wrong on the date. Eck. If it went sour just assume you aren't a good match and move on with life.

-Attempt to have the most perfect quasi-cinematic graceful yet lingering goodbye semi hug/kiss ever, but probably end up in an awkward hug or handshake. Shake your head in disgrace and hope you get another attempt.

-Never wait around for the call for the second date. Either step it up and call for a second date or make other first dates. Or better yet, do both.

-Try to enjoy yourself even though occasionally all of this seems like torture and you wonder if you would be better off to invest the $20 a month in a cat and a vibrator.

-Buy the vibrator. Consider it the best investment you've made in years.

Five first dates into this little dating project, this is all the wisdom I have come to know: write your date's name on your hand in case 2 IPA's in it is fuzzy and have a back-up plan, one that is preferably battery-operated. I have also learned to cut myself some much needed slack. I have not found love and I have not always been exactly graceful in my pursuit of it. But I'm out there making and breaking the should's of first dates. What I have really learned is there are no real rules to dating; there is just one great story.

If any readers have any additional tips or thoughts feel free to comment or email me directly at


The hardest part about a first date can be nailing down where to go. Try the following places for some laid back Tuesday night drinking options.


The Three G's
Guthries: A chill faux dive bar in Lakeview that specializes in good beers and board games in case the date is that boring.
Grafton: An irishy pub in Lincoln Square that fills with Old Town School of Folk students after class.
Glascot: A good choice for chillery in Lincoln Park with an option to order carry out from the Greek restaurant next door.


Webster's Wine Bar: The classic option. You will most likely be surrounded with other lovely couples on first dates. They also have fantastic entertainment depending on the night.
Frasca: Half price glasses on wine on Tuesdays. Enough said.


Fat Cat: Conveniently located by the Lawrence red line stop, this 40's style bar has $5 martinis on Thursday nights (worth breaking the Tuesday night first date rule).
The Southern: Although this bar specializes in whiskey they have some other great options like a Hot Bubba or Ginger Snap.

Previous Entry: The Two Necessities for Online Dating: Courage and Chicken Wings
Next Entry: Match in the Midwest: The Art of Polite Judgement

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Angie / October 20, 2011 3:12 PM

I also think some rules apply to your profile. For instance, I am a little sketched out if ALL your pics are of your reflection in the mirror or ones you have taken by yourself...really? No pics of you in public doing something cool? Or with friends?
Also, I can't stand when they say "We will lie about how we met", no need to be ashamed of it anymore, it's 2011! And is it really better to say "we met drunk at a bar?"

Lucas / October 20, 2011 5:54 PM

I was just telling my roommates how I like the jazz/rock show for the first date precisely because you can't talk. The tension builds while you think of something to say, and by the time you have an opportunity to chat, you're grateful for it. If the snippets of conversation were great, you hop over to another bar for the remainder of the night. If not, at least you saw some music. Am I the only one who thinks that's a good first-date model?

Niki / October 22, 2011 12:36 PM

@ Angie. I also have a very strict no picture in mirror rule. It is actually the only rule I’m not willing to break! see proof here:

@Lucas. I guess the caveat to the no concert rule is if your date is just super hot but not that interesting and you would actually prefer standing next to him/her and feeling the “tension” instead of talking, go to a concert, particularly a loud and crowded one. Just kidding with that actually. I think that the more first dates I go on the more I realize there are no rules or that none of them matter if you are hanging out with a cool/super hot person.

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