By: Leo_72

My ex-wife and I met Claire (not her real name, but close enough) during a summer share in Montauk. The two of them became friends, in part because we lived in the same area of Brooklyn. We knew a lot of people in common, we regularly bumped into each other around the neighborhood and many after-hours conversations started when we shared a cab going home. I wouldn’t say she was my best friend, but she definitely knew me very well—and I knew her well, too. The thing about Claire? She has never been lucky in finding a partner in crime in Gotham. 

You could say that she’s just another New York woman, struggling in a city in which single females outnumber single males, but there is something about her that simply doesn’t come across as girlfriend material. In any case, she had offered her help to improve my chances of getting back in the “sex in the city” game—and there she was, sitting next to me at the bar as we waited for our drinks.

The first tequila shot came, and she went off. “Pictures,” she said as if going down a list of essentials for online-dating boot camp. “You need one with a bunch of people, so girls know you have friends. Another one of you partying, to show you know how to have a good time. Then one of you doing some sport, so they know you can deliver a good physical performance when needed... No open mouths, no drunken faces, no selfies, no flirting to the camera, no pictures without a shirt (leaving that to the imagination is good). Understood?”

One hour later, we were letting the bartender choose our drinks. “Don’t overdo the funny character,” she went on, as if she were passing along the long-lost secret codes to online mating. “No girl will scroll down twice to read the text on your profile. Create some room for mystery, but not for weird questions. Make it clear that you’re a dad. Give them something to connect with you (quotes, bands, movies). Read their profiles, and then write them a message mentioning something you liked there. But don’t ask them out right away.”

We were predictably tipsy when the last call came. I got the check and walked her home. We were having a good time. It had been a while since I had laughed this hard with a woman. And then, at her door, she offered one more drink upstairs.

She seemed to be enjoying herself, so why not?

Taking your shoes off when you get to somebody’s place in New York is quite common, but this time it felt different. I saw her feet, her panty hose, and freaked out a bit. I thought about my ex, how she wouldn’t be precisely thrilled to see the two of us in that situation, but then I realized I didn’t care about what she thought. Yet, I felt the tension of the moment, my hands got cold... Was this really happening?

Claire pointed to where the bottle and glasses were as she took off her coat. She ran to get her laptop and laid on the couch. I brought two glasses of scotch on the rocks, we logged into my OkCupid account and she started editing my profile. She picked some Facebook photos of me and posted them, removed some stuff, sent messages to the girls I liked... She was excited about the whole thing. But was she just trying to help me, or was she also—eh—fixing herself a midnight snack? (Shit: no condoms.)

Claire did a great job pimping me out, I must say. And when she was done, we checked her own profile. I made some constructive remarks (no pictures with her dog, no “smart” in her description, bring the existentialist literature down a notch), and suddenly, that silence, that look. Noses touching. Smiles. A different smell, different lips, different taste.

It had certainly been ages.

She was incredible, I was grateful. I worked hard and gave a performance I wasn’t ashamed of—which was a lot to say given my lack of recent practice. A couple of hours later (probably less), I started dressing, but she made me realize that I couldn’t walk home because I didn’t live in the neighborhood anymore. And it was too late to take a cab in the cold, she added.

I couldn’t remember the last time I had had breakfast in bed. I felt like a mix of Steve Carell in The 40-Year-Old Virgin and Dirk Diggler from Boogie Nights. A newbie and a player at the same time. I enjoyed saying, “See you around” with a smile on my face as I made my way out.

Walking to the subway, I noticed a strange small new icon on my phone. What’s that? Not a new WhatsApp message, not a new text, not an email or a missed call.

OkCupid? A new message?


Leo_72 is a DJ and lives in Brooklyn. He can be found in dating sites under a slightly different nickname.