I slept with this guy years ago and he was kind of a jerk. What are the chances he’s still jerky?

I was set up with one of my friend’s coworkers about five years ago. We had a lot of fun – he’s cute, successful, smart. We slept together on the 3rd or 4th date and then for about 6 months we would go out every week and a half or so and I would spend the night. My friend had stressed that he wasn’t really looking for anything serious and I was fine with this arrangement as well. But then there was a stretch where we didn’t see each other for 6 weeks because we were both traveling for work. When we did finally get together I (respectfully, I thought) declined going home with him. I felt weird about just hopping back into bed with someone I hadn’t seen for months and probably I was starting to tire of the whole casual sex thing. Because of his high pressure job (and the golf and triathlons that seemed to come with it), he was always gone long before I woke up, which probably added to my feeling a little cheap. But of course, being 25, I didn’t say any of this to him, I just mumbled something about not thinking going home with him was the best idea. And he didn’t take it very well and we ended up not seeing each other again. At the time I thought his behavior was jerky, but now I think he just felt rejected.

Anyway I recently ran into him and we hit it off again. We’re planning on going to dinner. Its been 5 years… should I bring up the awkwardness from the past or just treat this as a first date? Should we even be going out? How do I keep us from falling into the same casual dating rut? I really do like him.

I’d like to see you bring that up. “So, you look great, nice to see you again. Whatcha been up to? Hey, remember that time I felt cheap and yucky because you often snuck out in the dead of night while I was sleeping after we had sex and sometimes I didn’t see you for long chunks of time and therefore rationally decided I didn’t want to sleep with you again, which angered you to the point where you were a total dick to me and we didn’t see each other for five years? Yeah. That was fun. Remember?”

The first step of not falling into the same rut is not taking your pants off and falling on top of him. I’m sure he’s cute and everything, and since you’ve slept with him already, it doesn’t add another guy to your Special Friends tally, but you need to resist. Go ahead and have dinner with him, but take it really, really slowly. (That means more than three dates before you sleep with him again, missy.) If you’re interested in pursuing an actual relationship, and you want to make sure he’s matured since the last time you saw him (don’t get your hopes up), give yourself a couple months of hanging out before you sleep with him again. This way, you’ll know if he’s suddenly going to re-join the early-morning triathlon circuit again or if he’s interested in more than just a friendly sex bomb now and again.

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