At this point in the Courtship Connection Chicago series, I’m shocked that Chicago made it to the Final Four for coolest city for lawyers. I have to assume that those voting weren’t taking the dating scene into consideration. Perhaps Above the Law could start a fund to transplant Big League from D.C. to Chicago, so that she could train her colleagues in how to have an exciting first date. (Step 1: Drink rye whiskey. Step 2: Visit a strip club.) My Chicago daters keep going on “pleasant” dates with “good conversation.” Descriptors like “nice guy” abound in their write-ups. Why do all have to be so darn… Midwestern?

Inspired by ExRated.co, moving forward, I’m going to force nicely ask lawyers in the Windy City to rate their dates (out of five stars), and list their legal eagle match’s best and worst qualities. Should the date not lead to a bedding, it can at least lead to a bettering.

The latest Chicago pairing involved two lawyers in their 20s. Asked why he agreed to be set up by a random legal blogger, our male lawyer, who described himself as “kinetic, adventurous, and faux-angsty,” said, “regardless of the outcome, it’ll probably be a good story, which is generally the important thing.” He asked to be set up with someone “outgoing and hilarious.” Our female lawyer volunteered that she has “HUGE brains.” That seemed like a decent match.

It wasn’t. Emo Lawyer thinks it’s because Mars Attacks didn’t drink enough. Meanwhile, she explained why: she couldn’t stand a second round with him….

Asked in the survey why she was willing to subject her love life to Above the Law for a night, The Brain said, “Oh god, I’ve only ‘dated’ one attorney since I’ve been here, and he was completely heinous: offensive, delusionally self-confident, not-that-good-looking, but tall (Midwesterners are tall!).” Given that, I was a little surprised she’d throw in her lot for a legal blind date, but she said, “Nonprofit salary doesn’t cover those law school student loans, and girl’s gotta eat (read: drink).”

I sent them to the Drawing Room on a Wednesday night. They didn’t choose particularly creative ways to identify themselves. He said he’d be in a black button-down, and she said she’d be in a blue dress. Luckily, our bruise-colored couple found each other easily.

Our faux-angsty Emo Lawyer says the date “was as pleasant as a nondescript first date could go.” Sheesh. You’re going to have to generate better lyrics than that to come up with Chemical Romance’s next hit. He had a suggestion for how Mars Attacks could have made the date more interesting:

After we were seated at the Drawing Room, we both got a Makers Mark-based cocktail (called “The Nooner” I believe. It was great)… Throughout the night, the server was extremely attentive. That’s normally great, but it made me feel as if I was a lush, as she was drinking at a rather fair pace. I know it’s a blind date, but come on. That’s more of a reason to throw caution to the wind on a Wednesday night.

I agree, Pete Wentz. There is an inverse relationship between boredom and alcohol on a first date. But Brainiac says it wasn’t her failure to knock ‘em back that made for a lackluster evening. She says:

I wish had a better story so I could give the people what they want, but alas, my tale, like the date, is a bore. Mostly everything about this courtship connection was aggressively mediocre. For starters, I don’t remember homeboy’s name.

I’m not sure how one achieves “aggressive mediocrity,” but I’m imagining it somehow involves pleated khakis. She says:

The place was pretty empty… The food was good, and my drink was pretty great as well. I certainly would’ve enjoyed a second, if I hadn’t been so eager to get home.

Well, that explains that. This date was too boring to warrant a second drink.

Way-Less-Angsty-Than-We-All-Hoped says Lisa Simpson “seemed like a nice girl.” He congratulated the two of them on “what one could hope for in a first date: no forced conversation, decent atmosphere and both of us refrained from playing with our cellphones for the night’s entirety.”

That’s not what I hope for. I hope for easy conversation, instant attraction, furtive groping, and playing with things that are not your cellphones.

Meanwhile, Brainiac says: “[Forgettable name] was a typical twenty-something, River-North-residing Cubs fan. <Yawn> But, he was pleasant, if dull. On a scale of offensive-looking to Marky Mark, he was totally neutral. If he’s a super-interesting and hilarious dude, my obligatory (and vapid) chitchat wasn’t breaking through any platitudes. I’m sure he was hearing the dial tone as well.”

Gee, Brain, I suppose it’s back to spending your nights taking over the world.


Kash is an editor emeritus of Above the Law. She now spends her days at Forbes writing about privacy, technology and the law at The Not-So Private Parts. For a background on the creation of ATL Courtship Connection, see My Weird Hobby: Matchmaking Lawyers.


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