Biglaw, Courtship Connection, Romance and Dating

Courtship Connection Chitown: Nothing To Feel Guilty About

Courtship Connection blew into the Windy City on the tail end of the summer. (You can still sign up here, single Chicagoans.) This week marks the city’s first two Courtship dates. One couple will go out tonight (good luck!). I’m hoping they have a better time than the two lawyers who met each other in front of a closed restaurant on Monday night.

The two Biglaw associates said there wasn’t “a spark.” Instead of a spark, there was a big height difference. It’s hard out there for the tall lady lawyers….

I sent these two Biglaw twenty-somethings to a restaurant chosen by our Amazonian lawyer. She chose the Gilt Bar (the website for which supports this thesis). Unfortunately, the daters and I were all ‘gilty’ of not checking the place’s hours. It turns out that they’re closed on Monday nights. He says:

Our date got off to an inauspicious start when I discovered that the place we met at — Gilt Bar in River North near Merchandise Mart — is closed on Mondays. I don’t frequent the area, so I quickly scanned Yelp for an adequate replacement. While immersed in my phone, my date showed up. Luckily, she lived nearby and led me to another place for a drink, though I would have preferred to go to Gilt. Oh well.

Think positively! Had this been a better date, this would have been a perfect date #2 spot.

Unfortunately, she says:

So I wish I had some phenomenal making out in the rain or awkward walk of shame story, but I think we both quickly realized that this date wasn’t going anywhere.

I thought these two would hit it off. He described himself as laid-back, an “easy-going food and music lover.” She said she was “sarcastic, athletic, and low-maintenance.” Perhaps I should have realized the athlete wouldn’t go for the bacchanalian. In describing their types, she said she’d go for someone tall and athletic, while he wanted someone who wore glasses. (Unfortunately, I didn’t ask for height or visual acuity in the sign-up survey.)

Apparently, this date got off to a bad start even before they met. Our Amazonian wasn’t a fan of what her blind date planned to wear to identify himself:

[It was] easy to find him given that he was the only guy standing out front of a closed bar, and definitely the only guy in a pink shirt and glasses. When I received that description, I was initially freaked out a bit: bold choice for a blind date, especially when you know that you are going to be described by what you are wearing. My douchebag radar was on high alert.

Time for an audience poll: do pink shirts and douchebags go hand in hand? (Or rather, neck in collar?)

Her caption: No, that's not him in the picture. Though I would go on a date with that guy."

Thankfully, my dbag fears were quelled upon meeting him. Instead, he screamed hipster. Not bad, given that I grew up surrounded by hipsters.

With Gilt Bar closed, we popped over to Bull & Bear to sit outside since it was a beautiful evening (see picture).

Not-A-Douchebag says conversation was easy, but that chemistry wasn’t:

We talked about our respective backgrounds and quickly realized we shared several acquaintances, putting me at ease. We talked about how we are both transplants to Chicago; I’m east coast and she’s west. We exchanged insights on integrating with the Chicago lifers, favorite tv shows, firm politics, and other small talk topics.

We stayed for two drinks and though she’s attractive and we got along well, she isn’t the type of person I would typically date  — the romantic chemistry just wasn’t there. So, I wouldn’t go out with her again, but we could probably be friends.  If our paths cross again through our mutual friends or otherwise, I would welcome the opportunity to hang out once more.

Speaking of “mutual friends,” our Amazonian beauty chastised me for setting up two Chicago Biglawyers, saying that these two might have ripped into each other more had their social circles not overlapped:

Once we found out that we were both junior associates at two of the largest firms in town, the conversation quickly turned to mutual friends. As it turns out, we have a lot of them. In fact, some of my best friends are some of his good friends. Lesson to Kash: Chicago is a small market compared to DC or NYC. When you pair two associates at the biggest shops, the probabilities of mutual friends are extremely high. And because of this, it makes it hard to be completely honest in a write-up.


He was a genuinely nice guy (sound the death knell), and we did have a lot in common. Both of us were deferred, both of us enjoy the Chicago food scene, and he grew up where I went to undergrad. We bonded over our love of college football (though I will forgive him for his alma mater), and discussed the upcoming season, and I learned that he is substantially smarter than me.

I think we both realized from the beginning that this wasn’t going anywhere, but it was nice to share a few hours of good conversation. There was no instant attraction or click there for me, though he is a good-looking guy. Of course, I was taller than him (damn giant genes), which is always a non-starter for me. And while he appeared decently athletic, I’m pretty sure I bench press more than he does.

Let’s hope Chicago pairings improve from here on out. In the meanwhile, if you’re tall, a little dumb, not too nice, don’t work for a large law firm, and are into physically strong women, send me an email. Our disappointed lady lawyer says:

I think I’m the only person in the world who loves blind dates (I pretty much could talk to a brick wall for hours if need be), so if you have another match, send him my way. Hopefully we don’t have so many friends in common, and then I can let my true snark come out. Or have a random hook-up with no qualms.

Either way, that would make for a more entertaining evening (and far more entertaining reading).

(hidden for your protection)

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