Dater X: The Curse Of The Second Date
People always freak out about first dates. But as a 30-year-old woman who’s been dating on and off for, oh, the past decade, I’ve mastered the art of a first date. You meet and have a drink to loosen things up. You talk about what you do, what you’d like to be doing, and where you come from. If it’s not going well, you can tell within 10 minutes and get the heck out of there. If it is going well, the conversation juts out in complicated tangents. You find yourself laughing, and leaning in closer. You realize that the amount of information you have about someone is increasing exponentially each minute. There’s the thrill of when you accidentally touch each other. And then there’s the first kiss, where you find all sorts of lovely idiosyncrasies, like that the bad boy has the softest lips you’ve ever encountered. No, first dates are easy.
It’s second dates that I fear. My first date with Chin Cleft was excellent. We’d exchanged a few emails on OKCupid, and he seemed like just my type—funny and whip smart. Since we happened to live in bordering New York neighborhoods, we met at a bar in between our apartments on a Wednesday night. I arrived first, and when he walked in, I was relieved that he was as hot as I’d expected. As he sat down, I couldn’t help but notice that he seemed nervous. He was obviously shy and a bit quieter than I am, but I liked that and did my best to make him feel comfortable. There was something sexy about him, and I kind of liked that he kept checking out my chest. By the end of the night, we were making out on one of the bar’s back couches. He walked me home and, after an awesome kiss, asked if I was free Saturday night.
On Saturday night, I found myself sitting across from Chin Cleft at his favorite Italian restaurant. We were only half way though the appetizers, and already the vibe felt off—we’d been talking about the weather for nearly 10 minutes. While I’d interpreted him as shy and sweet on our first date, now I felt like I was pulling teeth to get some real conversation going. Midway through dinner, I thought to myself, Maybe he just doesn’t have a lot to say?
But I wasn’t ready to give up. We had tickets to go see a band, and I wanted to give him more of a shot than that. Plus, I thought a few drinks could definitely help the situation. But at the club, it was the same—me asking all the questions, him giving shortish answers. When the band came onstage, we stopped talking to each other, except to exchange the occasional glance. Then, finally, he put his arm around my waist and leaned in for a kiss. And even his kiss wasn’t as blissful as what I’d remembered. Yeah, this just wasn’t the guy for me.
And still, I did something I do far too often when I’ve decided I’m not that into someone. “Want to come back to my place?” I asked.
Soon we were back at my apartment and I was straddling him on the couch as we made out. He slipped my shirt over my head and I did the same with his. From there, it was one of those sexual encounters that just went too fast—where, before you know it, your bra, skirt, and underwear are off and you’re completely naked in what feels like record time. So much for foreplay. Before I knew it, he was reaching for a condom. The sex was good—by no means great—but I’d had a month-long dry spell, so whatever. Afterward, he wrapped his arms around me and we cuddled. As my head lay on his shoulder, which was just a little too scrawny for my taste, I sort of wished he would leave.
Which kind of sucks considering that, 72 hours before, I’d been so excited about him. Darn you, second date.