You can’t wait until the second round of drinks to start being interesting

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….

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