Originally written November 16, 2011.
To the spaceman: You're a history of New York nerd like I am, and our first date was spent out-geeking each other in Lower Manhattan. However, I wasn't looking forward to the second date after I realized I wasn't ready for something serious. Pulling away and stiffening when you kissed me in darkness that simulated the space station, I never spoke to you again.
To my twin: I really liked you: tall, Jewish, and from the Upper East Side. We spoke as if we were old friends -- we're New Yorkers after all -- but I found out we were much too much alike. "You have an alcoholic father? I have one too!" That's not the kind of similarity I'd like to share in a potential mate, and the likenesses didn't end there. We're both "adult children," and though I found you sensitive (as I am), your obsequiousness repelled me: how you ached to please me because you wanted to keep me since someone who understands you is hard to find (I would know). I saw too much of myself in you, and if I wouldn't want to date me then I'm really in trouble.
To the cartographer: We platonically saw Sufjan Stevens in Prospect Park, and you convinced me to have a birthday party even though I didn't want to. We had a great time with gin and oysters, and my friends noticed how you took care of me that night. You walked me home, and I thought I was ready to date again. You slobbered while making out, and I didn't care since I was excited to see you again. Instead, I discover you're dating the hairdresser I recommended to you. Hope you told her how enthusiastically you went down on me.
To the brand-wearing name-dropper: You have an odd personality that first comes off as insincere, but you're a syncophant at heart. At first I didn't want to go out, told you as much, but dressed up anyway. You flattered by calling me a celebrity since we have a mutual friend. We cabbed it back to my place, and both a hangover and orgasm greeted me in the morning (I really needed the latter). I was surprised how easy it was to please you, especially since you did most of the work for both of us. Too bad that after a night of courting me, you told me to get lost after I expressed an interest in dating, whereas you'd like to keep it casual.
To my rolling partner: You don't fit in with the other guys since you're still in college, and we were both on drugs when we made out, but boy was it good. (Seriously, you could teach the cartographer a thing or two.) I would do it again in a heartbeat because it was so much fun. Half of me wants a round two as soon as possible, and the other half is afraid you'll reject the idea.
To the married man I'm dating: We're really good friends, and I thought there was nothing wrong with our "relationship" until someone pointed out that I'm dating a married man. I do this because you're a safe bet: you're not looking to break up your marriage, I actually do have a lot of fun with you, and we both realize your family comes first. However, the more I date you, the less I'm making myself attractive to men I can potentially date, fuck, and have a real relationship with. You were a good rebound from Prom King, but I'm ready for something new.