Last night, I went on a first date with the third man I've met on the subway. This guy is a Harvard grad, Class of 2003 which, by my calculations makes him about 28. We met on Valentine's Day on the 1 train headed downtown. He got on at Penn Station and we briefly met eyes while he was standing on the platform. Doors opened, he got on and sat next to me, iPod in ears. One stop later, he's taking off the iPod, turning to me and asking, "Is Christopher St. after 14th?"
Since I'll pretty much talk to anyone, especially if he's young and looks normal, I respond "yes." He follows up by asking if I'm from New York. I say no, and proudly boast that I'm from Philadelphia. I ask him the same and he responds that he grew up in Brooklyn, giving away that the fact that he obviously knows which stop is after 14th St. and he was just looking for an excuse to talk to me.
I love it and we both get off at Christopher St., chatting all the way. Since this is Valentine's Day, a fairly notorious night, I ask him what he's doing. He's headed to a third date. I give him my card and say "if your third date doesn't work out, email me." And it was weird, he kissed me on the cheek as he said goodbye. Like, um I just met you? I head to Meredith's with two bottles of Andre, then to a party on the top floor of an apartment building on the UES, like 79th and 1st. All I drank while I was there was white wine, and I went from fabulously tipsy to insanely drunk in about three seconds flat. Happy Valentine's Day, yay!
I heard from him that night. "Hey, It was nice meeting you on the train. Third date was fun but decided to head to Buddha Bar to meet 2 buddies after. Do you have access to email tonight? Best, D" We may or may not have drunkenly emailed a little bit that night, I can't say. Anyway, this guy is persistent. He emailed me for a week, but it was Fashion Week, and I kind of pushed him off. I didn't remember him being too cute on the subway. But constantly, emails: "What are you doing this weekend? Have you seen Slumdog Millionaire?"
Finally, we make a plan to have dinner on Wednesday, last night. He emails me the time and place, Vero, 77th and 2nd at 8:30pm, as he reverse commutes from Greenwich and doesn't get back into the city until 7:30. I meet him there, after confusing Vero with Bar Italia and not finding this guy I can barely remember. He's at the bar, he's very well dressed and pretty cute. We sit and I immediately order a gin & tonic to combat the awkward fact that we essentially know nothing about each other. As we begin to talk, I learn that he does research for a hedge fund and watches the stock market go up and down. He described it by shrugging his shoulders and saying "imagine a dart board." Putting his hand over his eyes, he mimes throwing a dart randomly at the board. "That's what it's like." He still has a job though and is actually expecting his 2008 bonus on Friday. I bet it will be a figure pretty close to my annual salary. We talk about how he went to Harvard, and I mention how I have spent some time in Cambridge, where an ex-boyfriend lives. He reveals that he used to play squash professionally, was ranked 100th in the world and traveled all over playing squash in clear courts everywhere from parking lots to shopping malls. He's a twin, which is weird because the first guy I met on the subway - Ted, you'll hear about him, is also a twin. What are the odds... Anyway, the twin brother and the older brother are lawyers and his parents met on Easter Sunday at P.J. Clarke's in 1976.
We have the cheese platter, but I have to say, I was really disappointed with his choice of drinks. Too girly. When I got there, he was drinking a strawberry margarita. Then, with dinner, he switched to sangria. Oh, and his favorite TV show is Gossip Girl. Uh huh, I know. Red flags to me too. We eat paninis for dinner with fluid conversation and I'm planning on heading home. He suggests grabbing a drink at Uma. We do, and I'm glad because we indulged in the best chocolate dessert I have ever had. Like a chocolate log, with cookie dough. I'm wearing a grey Alexander Wang cashmere dress, which he happens to adore the feel of. Hence, all the touching. It's kind of sweet though and the shoulder rub...feels so good. Then he kisses me. Surprisingly...not bad at all, which is rare because I'm (sort of) picky when it comes to who I kiss. He puts me in a cab at the end of the night and I'm definitely grinning, hoping to see him again.
We emailed today at work. He sent me one at 4:30, after the stock market had closed. "Another roller coaster day" he types. I'm not really sure what to make of this guy. On one hand, I think he might be kind of preppy, squash player brainless douche, but on the other hand, he went to Harvard, he's pretty smart and funny...too bad he's not taller. We'll see though. I'll definitely go out with him again. He's (ahem) loaded and smart and a good kisser. I'm all about it.
