Courtship Connection, Romance and Dating

Courtship Connections: Out Of His League

Dating sucks sometimes -- especially when it's a date set up by a legal blogger with no particular aptitude for matchmaking. Last week, Kashmir Hill thought she had actually done a decent job. She sent two Washington, D.C. lawyers out to Eighteenth Street Lounge on a Thursday night. Halfway through the date, the dude sent her an email, "Going really well so far." She thought she finally set up a date that was going well....

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Happy Tuesday, Above the Law readers. I hope you had a lovely weekend, spent staring deeply into someone’s eyes over a candlelight dinner, or rubbing up against a hard-bodied young thing on a dance floor, or fighting the cold by cuddling on the couch, or — if you live in Florida — doing all those things and more with your favorite barnyard animal for the very last time (legally).

If you had a romance-free weekend, do not despair. Dating sucks sometimes — especially when it’s a date set up by a legal blogger with no particular aptitude for matchmaking. Last week, I thought I had actually done a decent job. I sent two Washington, D.C. lawyers out to Eighteenth Street Lounge on a Thursday night. Halfway through the date, the dude sent me an email, “Going really well so far.”

“I finally have one that’s going well,” I enthused to my boyfriend. “Doubtful,” he responded. “If he’s excited enough to send a mid-date email, that probably means you set him up with someone who’s totally out of his league.”

I should mention that one of the things that I like in a partner is their being slightly more perceptive than me….

Our Big League lady lawyer had self-described as a “typical recovering overachiever” looking for a “witty feminist beefcake.” Our Little League male lawyer described himself as a “conversationalist, pragmatic environmentalist, world traveler” and said he was a romantic. His identifying item for the blind date, for the first time in this series, was a bouquet. Proof at right.

At 12:30 a.m., directly after the date, Little League emailed me:

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Just got home. Whatever is said to one’s face, one can rarely be certain of the other person’s frame of mind, but from where I stand it’s hard to argue that 4 1/2 hours, 3 venues, a number exchange and a tentative plan to get together again soon constitutes anything but a strong success.

Unfortunately, Little League did not bat this one out of the park. Big League says:

We met at the bar at Eighteenth St. Lounge and he (sweetly and boldly) brought me flowers. [After small talk,] we moved on to more interesting topics; we realized we’re both interested in secularism, the environment, and vegetarianism. I assume you matched us based on our favorite Justice — Ginsburg — but he also described himself as a feminist at one point, so props on that!

But not a beefcake, I take it?

[After two drinks] I was starving and we headed out to find some food. Somehow we ended up at Chipotle, which didn’t quite fit the vibe of the evening, but I was in a go-with-the-flow mood. And because nothing goes together like sex and burritos, we ended up in a long conversation about how neither of us believes in monogamy. As a general rule, first date conversation topics shouldn’t carry the subtext that if you keep seeing each other you’ll probably both end up with herpes.

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Save the STD talk for date #2, of course.

But what the hell, we were a couple of Manhattans in and I was pretty sure even a couple more wouldn’t make fireworks happen. He reminded me of an ex-boyfriend, and I apparently reminded him of his great-grandmother.

Really? And he was actually hoping for a second date? Gents, never tell a woman you’re hoping to see naked that she reminds you of a female relative. Especially one who has been wrinkly and smelled a little like moth balls for the entire time that you have known her.

In his version of the story, the faux pas was not quite as sexy-time repellent:

She asked the bartender if they had any rye whiskey, which doesn’t seem like the kind of request a place like this would get very often, particularly from a young woman. He said no, so then she decided to order a Manhattan, and I did the same. I told her that a Manhattan was the drink that my great grandmother liked, and because of that and the cherry I had assumed growing up that it was a fruity, girly kind of drink, which of course it is not.

Rather than recounting the history of the Manhattan, you probably should have immediately taken Big League to a place where she could get some rye whiskey and then avoid all conversation topics that involve your beloved great-grandmother. Save the endearing personal history for three months in, when your lady friend actually wants to discover your sweet, vulnerable side.

And don’t pass up an opportunity like this. He says:

We left Chipotle about 10:15 and walked back down the same block, passing by a strip club. She commented that it could make for a good anecdote on ATL if we went into the strip club, but on second thought decided it’d be better to just take a picture of it.

GO IN. Little League strikes out again.

Big League says:

Long story short, we had a ton in common and he seems like a great guy, but it takes more than that to make my stony heart go pitter-patter.

There will be no base-rounding for Little League. He says:

I would say that in terms of the flow of our conversation and the progression of the evening it was probably in the top 10-20% of first dates I’ve been on, which is impressive given that we didn’t pick each
other. Physically we weren’t touchy-feely, but it was just a blind date and we seemed physically comfortable with one another.

I followed up with her by text the next afternoon, and she replied that while she’d had a nice time, she wasn’t interested in dating.

Sorry about the bad call on this match, you two!

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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