Well, you’re already in danger of losing him as a friend now that you’ve crossed over into the “with benefits” realm. Sex instantly complicates any relationship. (Let’s just say, I haven’t gotten my mail in weeks.) People act like it doesn’t, but it’s a surefire way to make things awkward right quick. (Seriously, it was just a one-night stand. Can’t we be professional here, Mail Carrier Rita?)
You might think that you’re different than everyone else, that you guys can just hook up and nothing will change. But feelings always come into play, and now we’re past the point of worrying about whether or not he’s still going to want to come over for a casual evening of Wii and finger-blasting. So let’s not worry about that. Let’s focus on segueing this into a real relationship.
You could test the waters in the boyfriend direction. Instead of just hooking up, try to engineer a date night. Go out for dinner or a movie, then hook up. Have him stay over. Make breakfast together in the morning. Get him used to the idea of being a couple. Then hit him straight up your feelings, Paula Abdul-style. (By that I mean, dance it out.) Seriously, you’ve got to come clean at some point. Who knows, maybe he feels the same way. But swallowing your feelings and staying in this vague “friends with benefits” zone out of fear is just going to make you miserable.
What’s the worst that will happen? The friendship ends? Maybe. But then maybe you take some time off from each other, and rekindle the friendship once you’ve moved on emotionally to someone else. Or maybe this will be the start of an amazing relationship that just needed you to kick its pokey ass in the right direction.