Sex Diaries: Have You Ever Planned a Hookup?

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Editor’s note: Virginia Plain is the pseudonym of a twenty-something woman living in New York who just ended a four year relationship. Read her previous posts here, and check back next week for more.

Ok, so last week’s adventure was a little crazy. And by crazy, I mean crazy awesome! But seriously, I realize that sort of anonymous spanking/blow job extravaganzas in swanky hotel rooms aren’t going to happen every weekend and that’s probably a good (at the very least healthy) thing.

Plus, I’ve got something better to think about: I’m going to see Crazy Jacket again.

As you may recall, Crazy Jacket is a weird Australian manic pixie rock star I met recently and had an amazing cuddle session with. To be honest, I really never thought I’d see him again which I was sort of fine with since I was a bit ambivalent him. But it’s funny how a little time and space can completely change your opinion about someone.

The more I thought about this guy in the following days, the more I realized I liked him. Yes, he was intense and certainly wild, but he was also really nice, and surprisingly respectful and completely engaging in conversation (i.e. he didn’t just talk about himself — a woefully rare quality.) There was something really magical about him and his completely unabashed free spirited nature. Crazy Jacket was, in so many ways, the exact opposite of Real Estate.

I couldn’t help thinking back on that night constantly; reliving every exchange, every glance, every smile. I thought I’d be (sort of) happily mired in those memories until my trusty roommate discovered that his band would actually be back in our neck of the woods due to a few rescheduled tour dates. Immediately she got us tickets and started looking into renting cars to drive the few hours to the city they’d be playing.

It was settled quickly, before I even really had time to think. I’d be seeing Crazy Jacket again. Soon. While I should have been excited, I was honestly a bit terrified when she told me. Because the bottom line is, I could actually sleep with this guy. And the last time I slept with a new guy was four years ago.

Now, clearly there have been other hookups. But I tend to prescribe to the Bill Clinton definition of sex in that blow jobs really don’t count. Sure, it’s sexual. But putting a dick in your mouth will never have the same weight or impact as putting a dick in your vagina. It just is not the same thing, to me at least. Obviously sexting doesn’t really count either.

Since, we’re on the topic, I’ll also mention that I haven’t actually slept with that many guys. Just my high school sweetheart, this sort of random dude that happened over a pretty bizarre Christmas holiday, and then Real Estate. That’s it. For a girl in her mid-twenties that just seems kind of depressing. Not, that you have to run around jumping into bed with every single person, but damn, that just isn’t a lot of experience. Certainly not a lot of good experience. It’s enough to make a girl question her newly minted vixen status.

Talking to another friend about this whole situation, I admitted that I kind of had “virgin anxiety.” Clearly, not a virgin over here, but it’s been a long time since I’ve really been with anyone else and I’ve sort of reverted to those weird “OMG, I’m going to have SEX” tremors you feel right before it happens for the first time. Jesus, I’ve never even had to buy condoms (something boyfriends don’t seem to mind doing.) Excuse me, did I just time travel back to high school?

So, I’m wondering: have you ever planned a hookup? In a way, I’m glad this little opportunity popped up because a.) I think the chances of actually sleeping with Crazy Jacket are at least good enough to merit the journey and b.) I’d much rather my first time post-Real Estate be with him than just any dude I pick up in Williamsburg.

But. It’s such a grand gesture to make this little trip to see this guy I really wasn’t supposed to see again with the express purpose of sleeping with him. The more I think about it the more I see the cracks and holes and how things could wrong. What if he isn’t happy to see me? What if he is? What if we do hookup and it’s terrible? Actually caring makes things way more complicated. Maybe that’s why hipsters are so apathetic.

I’m running out of time to think about this though, because it’s happening whether I want it to or not this weekend. I guess I should start planning my ultimate seduction outfit.

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