I recently moved to town and moved into a house full of 20-somethings I didn't know. One of the roommates and I instantly hit it off, and hooked up pretty much immediately. Save for a few random hookups by both of us, we've been "exclusively" sleeping with one another for a few months. We enjoy each other's company, we have similar taste, we go on date-like outings and act affectionate in front of our roommates. In any other situation, I think we both would be trying to make this a more serious thing, but I think the fact that we live together is making us both hesitant. We've made it clear that there's a mutual attraction, but we never discuss our "status." Are we asking for trouble, or could this be the beginning of a normal, healthy, monogamous relationship?

Anonymous

So, first up, your use of the word “exclusively.” To quote a wise man: “I do not think that word means what you think it means.” When you say that you have “made it clear that there’s a mutual attraction,” do you mean the part where you’re sleeping together, or has there been an actual conversation about this? Because short of some real discussion, it looks to me like you have a fuck buddy who is very conveniently located for booty calls. On the other hand, if you have actually talked to each other about the fact that you like each other but are worried about your living arrangement, I don’t see why there is an issue here. You found a place to live pretty easily, and you can do it again if need be, right? And it isn’t like you are in a position to avoid drama now, anyway, so you might as well go for it.

So, there’s this guy I dated in high school. I was young and crazy and I had a crush on him for, like, a year before his friends finally convinced him to ask me out. It was fun for awhile, but we ended up not being that good together because he was always too cold to me and too worried about school and sports and stuff, and never paid enough attention to me. I cheated on him (by kissing another guy at a party) and then confessed, and then he dumped me.

Over the next few years, we were still in the same group of friends, and it wasn’t really a big deal. It was high school, and a lot of people in that group dated each other and nobody really cared. Whatever. So, then we went off to college and we had a short little fling there for a couple months. And the thing is, I really liked him, and I really thought that we were going to end up together—a lot of people thought we would, for some reason. But the same stuff happened again, and it didn’t work out.

In the meantime, I ended up being really good friends with his younger brother. We have a lot more in common, he is only two years younger than me, and we hang out together a lot. The only time there is a problem is when we run into certain people from the neighborhood who make fun of me. They say since I couldn’t have the older one I am settling for this brother, and it really makes me angry and hurts my feelings, but even worse, I think it makes my friend wonder if I am using him to get to his brother. I am not. No way. We do not talk about the brother; I never ask about him. We don’t see him very often because we like to hang around in different types of places with different kinds of people than his jock older brothers.

It has been five years since I was with the older one, and I am worried about losing my friend. Even worse, I am starting to think I might be having feelings for him. Like I said, we are way more alike than I was with his brother, and I am not thinking of him as second best at all. Now I wish I had never dated the other one and I don’t know if I can do anything or just stay best friends because of the past.

Living in the Past

I am not clear about exactly how long you and the younger brother have been friends. It sounds like, at least from your perspective, the two of you are very close. If that is true, and if you are best friends, then you shouldn’t worry about what other people think. If your friendship has been going on for years, then you probably know this guy well enough to know how he feels about you, about your past with his brother, and about what other people say about your relationship. In which case, you may want to hold back for a little while and see where your feelings go. I mean, you don’t want to open this can of worms for feelings that you think you might possibly be developing, right? So, hang in there awhile and keep quiet and if you still feel the same way or if your feelings get stronger, then tell him in a couple months.

If your friendship is new (or newish), then you definitely need to keep quiet for now. Develop the friendship, get to know him better, and then if you still like him and you think he might like you back, then you can spring it on him. If the two of you are really compatible and make each other happy, everything else will just fade into the background. The nice thing about old neighborhoods is that if you want to you can get the hell out of them.

Confidential to Lucky Charms: Don’t do anything that would actually harm her. Leaving foreign objects in somebody’s food is petty and gross. If you want to send a message, try writing it on paper and leaving that for her instead.