Have you ever slept with your roommate? What should I do?


Brian from Ohio asks:

I met a girl a few years ago. I was attracted to her, but she had a boyfriend at the time. We live in the same city, and would see each other in bigger groups occasionally. When she broke up with her boyfriend I was dating someone else. I eventually broke up with that girlfriend, but for some reason assumed the first girl wasn’t into me.

About 5 months ago her lease was almost up. I live in a 4 bedroom apartment, and she asked if there were any spots available. The timing was great because one of my three male roommates was moving out and we needed a replacement, so she moved in. Once we lived together we started hanging out more over the next few months: going hiking, going to the farmer’s market, getting beers together — all things I used to do with my male roommates, except since I’m a guy and she’s a girl sometimes it felt like we were on dates.

The lines started to blur a little more: sometimes if we were drunk we would cuddle on the couch when we were watching Netflix. One night I went in for a kiss, but she didn’t want me to kiss her, so I assumed she wasn’t attracted to me.
Then, a few weekends ago we were out with some friends and she was touching me a lot more and giving me signals like she actually was into me. The next night I went for a kiss and long story short we ended up having sex. The sex was really good (like one of the better times in my life, and I think I have a good amount of experience) even though it was only the first time between us.

I wasn’t sure if she wanted it to just be a one-time thing, but later that week we had sex again, and it was even better. I feel a strong connection with her since I spend a lot of time with her, and that might be why. So far we haven’t really discussed the relationship. I think I should probably talk to her soon and try to define the relationship, to see what she wants, since I’m not sure whether she wants to keep things casual and just hook up from time to time, or become boyfriend/girlfriend. It seems like this could end badly, since we live together, but I still think it’s much better than we cut the sexual tension by finally hooking up instead of trying to stay platonic.

Have you ever had a female roommate you were attracted to who was also attracted to you? What are your thoughts about this situation? What would you have done?

Demetrius says:

To start, I’ll be upfront and say no, I have never had a roommate who was a woman, nor one who I’ve slept with. I’ve been fortunate in that I haven’t had a roommate in like, 10 years, and the last woman I did live with was, at the time, my girlfriend. But, despite that, I think I can relate, because when you simplify the question a bit it’s pretty relatable. If you’ll let me, here’s how I’m looking at your question:

I’m friends with someone I’m attracted to. We have a close relationship and see each other frequently. Recently, we hooked up, and I’m not sure what I should do next.


The roommate details are important, but when you get right down to it, that’s pretty much what you’re asking. Don’t worry, I’ll tackle your specific issues a little later in the post.

In any situation where you already have an existing platonic relationship with someone, and things suddenly take a sexual or romantic turn, there will always be doubts about whether or not it was the right thing to do, and doubts about how to proceed. One thing I recommend that you or anyone remember is that the past is past. You’ve made your bed, both figuratively and literally, and now you have to lie in it. Or you know, get out of bed and make it. There’s no taking back what you’ve already done, so whether or not it was a good idea, or whether or not I would have hooked up with a hypothetical roommate, isn’t really that important. For the record, I’d like to say I wouldn’t hook up with my roommate if I were in your position, but given my own judgment in similar situations, I’m almost certain I would do exactly the same thing. Without giving too much about my own sex life away, let me just say that I maybe have had romantic dalliances with some people who I had a close friendships with. And maybe, just maybe, I came to question my own judgment after these dalliance, and worried about how to proceed. Maybe it wasn’t the best idea at the time to sleep with these hypothetical friends of mine, but it doesn’t mean that you can’t make smart decisions moving forward. You can’t change the past, but you can make the future.

 While you can’t take back the things you already did, you can decide how you want to move forward. Just because you’ve kissed a friend, or slept with them, doesn’t mean that you now have to suddenly enter into a relationship, sexual or otherwise. You might not want to lose a friendship, or make things awkward between you two, but it’s probably a better idea to talk about what you are, what sex meant, and where things might be going.

With all that out of the way, let’s dive into your question Brian. It seems like you like her, so how you proceed is really going to come down to what you want out of your situation. If you want things to go back to the way they were pre-hooking up, which it doesn’t sound like is the case, but I’ll just cover my bases here, it’s best to bring up what’s happened so far less in a “let’s define things” sort of way, and focus more on how best to move forward as friends. If that means taking a break from spending alone time together, or avoiding bringing new people over to the apartment for a while, that’s what it’s going to have to be. If you want to go back to being platonic, keep in mind that things will never be exactly what they were before you hooked up. For either of you.

If you want things to be romantic, but you’re indifferent about whether you want a relationship or not, just ask her what she’s looking for. It’s entirely possible she wont want things to go anywhere in particular either, or maybe she just wants to hookup occasionally, or maybe she does want to see where things could go. Either way, if you like her but don’t really care one way or the other how your romantic relationship will progress, just ask what she’s looking for in a general way.

If you do have your heart set on a specific outcome, you need to frame things less as “what are you looking for?” and more like “what are you looking for, because I am specifically looking for this”. It might lead to an awkward conversation, an end to your fledgling romance, or a really productive conversation, so be prepared for each of those outcomes. If you haven’t noticed the trend here, I’ll spell it out for you. Decide what you want things to be, prepare for the worst case scenario, and have the conversation soon.

Normally I’m hesitant to push for any sort of relationship defining talk to happen as soon as possible, but in this case,  I think you need to have this conversation sooner rather than later. Because you live together, any misunderstandings or assumptions either of you might have about what things are between you two will only be magnified because you live footsteps away from each other. All of the time-frames I’d normally suggest for relationship defining talks go out the window when you live with someone. It doesn’t have to be tomorrow, but I wouldn’t wait for a specific milestone like a certain number of dates, or how long you’ve been sleeping together. You can always frame the conversation exactly the way I’m framing it, with more warmth obviously. It might be reassuring to her that you’re taking the initiative so that you’re both on the same page. Or not, but honestly, I always recommend being the one to make things awkward, rather than being the one who puts having this conversation and causing enmity between you two. Oh and one final suggestion: Because t’s usually an awkward conversation, start it off by saying something along the lines of “Hey, just wanted to talk about us/what happened so we’re both on the same page” because that sounds much better than “We need to define our relationship”, especially if she doesn’t want a relationship.

Above all else, just recognize how messy this specific situation can be, and prepare for the worst. No matter what you decide to do, whether you want to go back to being just friends, push toward a relationship, or occupy the gray area in-between the two, things could turn awkward.  That’s true of sleeping with anyone, but especially sleeping with friends. Even more so when you sleep with your roommate. Things could turn out great too, don’t get too hung up on my pragmatism, I just find it’s smarter to spend more time preparing for the worst.

Whatever you decide to do, give it some real serious, consequence driven thought, but don’t wait too long to have a talk. If you’d asked me before you slept with her, I’d have cautioned against it completely, but it’s not hopeless. Who knows, maybe things could work out here, and now you’ve got a live in girlfriend/partner/sex-friend. Whatever happens, I wish you the best of luck.

Good Luck Out There.

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