Freak of the Week: Not That Complicated

Dear Freak of the Week,

I’m a ’27, and I’ve been friends with this guy since freshman year. Although I’ve always thought he was a little bit crazy, he’s also nice and we get along great. Something strange happened recently. We were hanging out one night, and we randomly started kissing. I’m not even sure who initiated it, but I liked it. We went back to his dorm and had amazing sex. As soon as it was over, he seemed like he immediately regretted it and talked about how it would mess with our friendship. Fast forward about a month, and this same exact scenario has happened three separate times. I don’t even know if I want anything more than what’s been going on, but I’m just so confused! Please help.

Sincerely,

Not That Complicated

Dear Not That Complicated,

Wow. If I didn’t know any better, I’d say that your position is enviable. It looks like you might be on the verge of an awesome romantic relationship with someone you’re already friends with, which I’d argue is the best way to start a new relationship. Upon closer examination however, this enthusiasm might — definitely — be misguided.

First off, I want to acknowledge your description of this person as “a little bit crazy.” I don’t know what you meant by this, but given the situation, it seems like our character is living up to the hype. A person who has the gall to simply start kissing someone that they’ve been friends with for years is some combination of impulsive, ballsy and daft. His behaviors after you hook up are further indicative of these traits – it seems like he is either consistently shocked by how his desire clouded his judgement, or he’s genuinely worried about maintaining a friendship with you. I’d argue that in this case, the former is more likely. 

This combination of things makes me inclined to predict that this guy is likely just bored. He might see you as a hookup that he has now established as relatively regular and he doesn’t know that many other people.

I think you have a pretty straightforward decision to make here. If you say that the sex is amazing, you could just let it ride and enjoy. At the same time, it’s perfectly legitimate to feel used and also be offended by his reactions after you two get together. You could also consider having a conversation with him about these, and then opting to continue. 

Overall, I’m pretty confident in telling you that this isn’t something you should consider for long term potential, as long as this guy stays the way he is. Enjoy the messiness!

- Eli

Dear Not That Complicated,

Even though this guy alleges that he regrets the intimacy, the fact that this occurrence has happened three separate times points to the guy not truly meaning that.

I think since he doesn’t know how you feel, he’s gauging your feelings by saying that what you’re doing is wrong and will ruin the friendship. When he talks in this way, what do you say in response? I wonder whether, if you challenge him, he might actually feel relieved.

However, one thing to consider: the fact that he is, in your words, “crazy.” I don’t know what you mean by that, however if you are considering a more serious relationship with him, you should also think about the aspects of his personality that may be okay in a friendship context, but wouldn’t mesh well with you when you’re dating.

I am going to disagree with Eli: chronically single people at Dartmouth are not necessarily exhausting their options. There are lots of people at Dartmouth, especially after your freshman year when you start to mingle more with different grades. People at Dartmouth are generally too awkward to accomplish the feat of running out of eligible suitors because they hooked up with too many of them; usually they are too shy or assume that the campus is too small anyway. In brief, this guy has not exhausted his options of people, and you are not his “last resort” or anything like that. If nothing else, he cares about you and the friendship, and may be confused about his feelings.

It seems like you don’t really know what you want yet, and that’s okay. But next time you’re together and he says something about how wrong it is, ask him why he believes that.

Good luck!

- Leila