There are two ways you can handle a date after you realize you’re not a match. You can shut it down, giving this person you will never see again as little energy and effort as humanly possible, or you can have some fun. You can say, “I’ve got to be up early tomorrow,” or you can say something you’ve never said on a date and see what happens. Like, “I’m throwing out my nail clippers and going with bite-only trimming from now on.” Or, instead of asking for the check, order a Clamato Bloody Mary and see how it flies. Rather than asking about her family, ask about the last person she wanted to murder. I’ve done all of these things, and, admittedly, each one was a complete disaster, but at least I got something interesting out of the evening. I’ll take that over two forgettable drinks any day. Who knows, if you pledge to do the unexpected you might just find out you’re sitting across from a heroine user – and isn’t that what Internet dating is all about?
The moment I arrived to meet Courtney, I knew something was up. She lived in a neighborhood I’d never been to, so I let her pick the bar – something my chivalry, or at the very least, my desire to fake chivalry, would never normally permit. When I got to the bar, it was dark. Like porn movie theater dark. I understand the value of ambiance, but the mood said less “romantic rendezvous” and more “hide my horrific cold sores.” It was an odd location to meet someone you were hoping to recognize from a two-inch picture, but I tried to keep an open mind. I sat down under the brightest available lightbulb and waited for Courtney to arrive.
A few minutes, the door opened, and while I couldn’t see the lady’s face, I had a strong feeling it was her. Why? Because I could see these…
We weren’t going to the ballet later. We weren’t at some hip little cocktail bar where the bartenders wear visors and every drink is named after a dead abolitionist. Hell, we weren’t even in Manhattan. But for some reason, Courtney was wearing a sequins top, knee-high black boots, and a long pair of white opera gloves. It’s the sort of thing Catwoman would wear on a date. Which is fine if you think I’m gonna propose, or if, say, you know my last name, but we were in a dingy little dive bar in Crown Heights, Brooklyn which she selected. The first half-hour of Syriana made more sense than this. All of a sudden, I was feeling the urge for some clam-flavored tomato juice.
We talked for a while, and it was clear that Courtney and I were not a match. Through the darkness I could see that my attraction wasn’t strong, and clearly we had different tastes. She liked going all out: fancy clothes, fancy parties, fancy tastes. Meanwhile, my idea of a perfect evening includes an expertly TiVo’d episode of The Good Wife, and perhaps some low-level intoxication. There would be no second date, but that didn’t mean I couldn’t still make our first date as interesting as possible.
To find out just how interesting it got, buy my new book Not a Match: My True Tales of Online Dating Disasters. Contains the Girl Who Took Heroine, The Sex Crier, and all the It’s Not a Match classics. And yes, I use the term “classic” loosely.