Courtship Connection, Romance and Dating

Courtship Connection Chitown: Hush, Puppies

Sadly, the percentage of Courtship Connection blind dates that lead to second dates is far lower than the percentage of ladies at One First Street, though it’s higher than the ratio of Supreme females to Supreme males dating back to the Court’s beginnings. Barely.

One of the couplings that did beat the odds included two New York lawyers paired because of their shared love of My Cousin Vinny. Seeing that two Chicago early-twenty-somethings had named Vincent Gambini as their fave legal fictional character, I sent these two yutes out on a date, hoping to replicate that success.

She self-described as a “cute fun firecracker” looking for a “hilarious (like really ridiculously funny), goal-oriented, and tall” legal dude. He said he was a “gunner w/sense of humor” whose type is “good-looking, smart, intense but funny.”

Firecrackers + gunners should make for a fiery night, right?

They met on a Thursday night at Southern (which seemed appropriately named for the Vinny theme). To identify himself, Funner Gunner said he would be wearing a “straightforward black v-neck or button-down shirt.” He says:

I got there a bit early, and I sat at the bar (with my back to the door) watching baseball.

Really? You start a blind date by sitting with your back to the door while wearing something completely unremarkable? Regardless, the date got off to a good start, as Cute Firecracker was remarkable enough to catch the attention of the bartender — who then pried Gunner’s eyes away from the TV:

At one point, the barback came up to me, pointed at a girl, and said “you know, I wish more blonde girls in blue and black striped dresses would walk in here!”  He went on for a bit longer about girls who show up at this restaurant to meet people and end up leaving alone, and was really embarrassed when it turned out that the woman he was talking about was the one I was going to meet.

Well, telling her that story would have been an excellent way to start the night off with a bit of non-obsequious flattery. But it sounds like he kept it to himself. Female Firecracker says:

We talked about job hunting since he’s doing it and I haven’t been off the market too terribly long. He admitted that the key item on his list for prospective jobs is that he be able to take his shoes off at the office and walk around in socks. I thought this was strange, possibly unhygienic, and imagine that he would end up with a lot of really dirty socks.

Um, this is the same “cute fun firecracker” who said she was looking for someone with a sense of humor?

Since I could tell right away that it wasn’t going to go anywhere I told him about a poll my co-worker and I took at work earlier that day (I have trouble not saying things that cross my mind) – “should guys pay for the entire date or should the girl split it?” The overwhelming consensus was that the girl should offer, but ultimately the guy should pay. He was adamant that he would never let a girl pay for the first date, which I appreciated (even though my co-worker finds it sexist). After telling him about the poll I immediately felt guilty, as I realized I had probably shamed him into paying even though the date wasn’t going anywhere.


I really made an effort to split the bill, but he wouldn’t let me. I would gladly have done so and wish that I had had more cash so that I could have forced it on him. After all, he’s still in law school and I’m already a working girl.

You are indeed guilty as charged. Speaking of, why the need for cash? You could have charged, couldn’t you have?

All bs aside, there just wasn’t a spark and he must have realized it too because he didn’t bother to ask for my number.


He says:

We sat at The Southern for about two hours, had two drinks and some hush puppies, and seemed to talk about work / school the entire time. She seemed to be going on a lot of blind dates because of the pressure to be in a relationship; I was more interested in having a new drinking buddy.

Friends with drinking benefits? Do you really need my help to find that?

She was perfectly nice and pleasant to be around, but it was a total mismatch.

Firecracker has a better match in mind for herself: Not-A-Douchebag. “Unlike Amazonian that went out Monday, I would have loved to be set up with a fellow big-lawyer,” she says. “In fact, typically I wear contacts but maybe pink-shirt and I should give it a go and I’ll break out my glasses. I appreciate dudes in pink shirts.”

Earlier: Chicago Singles, Get Excited: Here Comes ATL Courtship Connection!

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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