Michael: In my opinion the third date is traditionally the one where you have sex. Does Holly feel that way? I don’t know. I will probably find out tonight. If she starts having sex with me I’ll know for sure.
Ah, the elusive third date. I’m trying to recall all the third dates I’ve had – and how they ended. As many of my regular readers [and real life friends] know, in my past dating exploits, I rarely got to the third date.
Actually, I think I only had proper third date sex once.
It was B, a guy I worked with – and the first guy I hooked up with after The Ex and I broke up. Though the first time we went out, it was just to a bar. The second time, he came over, spent the night, and we hung out all the next day. Twenty-four hours in total. That was a mega-date. Then the third time we hung out, he came over after work, and spent the night. It culminated in sex. He never called me to go out again, and five months later, I heard he got married.
Only one other guy I had sex with took me on a date. That was D. We met at Fenway. And even then, like with B, they were those borderline dates. We had sex on our second date. I awkwardly cried in bed before we went to sleep. He held me. I don’t remember why, but he was sweet. We had sex the next morning. He never called me to go out again, but I see him around the Park from time to time.
The other seven guys I had sex with were all drunken one-night stands. Two of the guys I was friends/acquaintances with before, but don’t really talk to now. Another guy lives in my neighborhood. He saw me with my girlfriend recently. He kissed her hand, said, “Hello, Gorgeous” and awkwardly walked away. The rest I am okay with never talking to again. Except one: he lives in Ireland. I still talk to him. He and I actually had sex two separate times [the only repeat performance], and I thought I was kind of in love with him. I even sort of proposed on our way to the train station. He accepted, too. So I think I might be engaged. If he lived here, and I didn’t have my girl, I might try to make something happen with him. He was the best sex with a guy I ever had.
On the other hand, there were several guys I went out with more than three times that I never had sex with. A couple last year, and more before I dated The Ex. The only reason I can think is that I just really wasn’t attracted to them. And maybe I really just wasn’t attracted to guys in general. When my girlfriend came back to my apartment after our first date, we made out. We hooked up the second night. I was very attracted to her. And even though at first it was awkward, and I wasn’t sure if she crazy or not, I liked her.
We’ve been together for almost 4 months. I can’t remember if we had sex on our third date. But you know…I don’t think it matters.





