Happy Valentine’s Day to you if you have a date lined up tonight! For the rest of you, Happy Staying-In-To-Watch-A-Movie-And-Drink-With-Your-Single-Friends Day. Last year, two Washington lawyers actually let me set them up on a V-Day date. This year, with my pool of Chicago candidates, I didn’t bother. I wouldn’t wish the boring Chicago dating scene on my worst enemy. Playing matchmaker and condemning more lonely souls to a yawn-inducing evening is as cruel as running a dog-fighting ring. At least the latter leads to a little biting and scratched backs for the participants.

So Courtship Connection is moving on and heading West. Hey San Francisco, do you have any single types willing to put their love lives into ATL’s not-so-capable hands? Fill out our survey! I will try to send you out on a blind date with a seemingly-compatible fellow legal type. You will dish the dirt afterwards. I will write about it, keeping you anonymous. And ATL commenters will provide their sincere, caring, and helpful commentary.

While waiting for the California girls and boys to jump into our dating pool, I will share with you the final Chicago date. Like the others, it did not go well. Why? Someone’s inferiority complex killed the mood….

There was a mutual attraction between these twenty-something lawyers, which seemed promising, especially given their low expectations for the night. She says:

By date night, I wasn’t exactly looking forward to meeting this guy. We met at Rootstock, a bar that sounds a little casual-pretentious and isn’t close to my office or my apartment. Kash told me I was looking for a dude carrying the Chicago daily law bulletin and wearing jeans, blue and white striped shirt, and black-framed glasses. Really? The men’s casual uniform is supposed to help me identify you? And what does the daily law bulletin even look like? I feared I was meeting a law student who was trying too hard.

The poor blind-date clothing selection by Men’s Casual may have been from lack of experience. He says:

I’d never been on a blind date nor had I been on a totally blind date set up by someone that I had never met. That said, I am usually willing to give anything a try. That’s exactly how I got submitted for consideration to the ATL Courtship Connection: One of my friends decided to sign me up for this and I decided to go along with it.

Okay, so he’s not the type to take charge, but he is willing to roll with an adventure. That’s not terrible.

Our lady lawyer brought a coffee cup to identify herself. Starbucks Mermaid says she arrived five minutes late; Men’s Casual says she was right on time. So they’ve already got that going for them… She said:

Dude was cute and super nice. He was not the douchey law student I dreaded, but an associate my age. Conversation came pretty easily. We talked about sports, bad tv (but isn’t it all bad?), and work. Lots and lots of work. I suppose this is okay; I still love my job as a junior biglaw associate, which is why I don’t mind talking about it. And he’s more experienced and at a smaller firm, so it was interesting to hear about how his practice differs from mine.

Cute, nice, and experienced? She sounds hooked. He says:

After the initial awkwardness of being on a blind date subsided (all of about thirty seconds) we quickly went about getting to know each other… My hope was that I wasn’t going to do anything that would open myself up to massive humiliation on the pages of this website. Since I am a klutz, I was fairly certain I would spill wine all over myself or her at some point during the night.

Rest assured. No clothes were harmed in the making of this date.

We spent the next two or three hours talking about every topic that we could cram into the conversation. She was a cute girl, extremely intelligent and plying her trade in the halls of BigLaw. Lord only knows what she thought of my law degree from an online university (kidding) and that I am one ambulance chase away from being a cheesy lawyer joke (somewhat kidding). It was definitely two different worlds being represented at the table that night and I enjoyed spending time with someone that wasn’t doing the exact same sort of work that I do.

Danger, danger. Self-deprecation is not a turn-off, but a true sense of inferiority is. He sounds like Aladdin having dinner with Princess Jasmine here. Unfortunately, Men’s Casual didn’t have a chance to rub a magic lamp, or anything else:

Two or three glasses of wine and a cheese tray later, we called it a night. I walked her to her car and we said good night.

Starbucks Mermaid did feel a little like a fish out of water:

I was a little distracted by the venue, which I disliked. Rootstock is the kind of place with mismatched furniture and dishes, and 7,802 beers and wines on the drink list. Places like this annoy the shit out of me. If you order wine at a small establishment with a bloated wine list, you’re likely to get a glass of last night’s bottle. Ew. I also don’t think it’s cute when chairs look like they came from Goodwill and dishes are chipped. This isn’t college, Rootstock. I don’t hold the bar selection against my date because it’s a decent neighborhood bar and close to his place, but I’d have preferred a more straightforward establishment: a nicer wine bar, a dive bar, or even an ultra-hip $20-martinis bar.

She continues:

While I had a nice time and gave him my number, I am a little on the fence about going out again. I also left without sufficient information to launch my standard google/facebook investigation, which puts me at a bit of an information disadvantage. Whoops. All in all it was a nice night, which is all you can ask for on a blind date, right?

Unfortunately, Men’s Casual never called Ariel. When I asked him why, he said:

Nope, there was no second date. I do wonder if there had been what would have transpired but it just never did.

Ladies and gentlemen, that attitude is how we end up single on Valentine’s Day. We need a little more carpe diem and a little less carping about your different worlds.


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