Should I hook up with my roommate? We were friends before we were roommates, and I always thought she was attractive, but she was in a relationship so I knew it couldn’t go anywhere. When we moved in together about 10 months ago, I told myself I needed to stop liking her since we were going to live together (plus she was taken). Well, her relationship just ended and she’s broken-hearted. I’ve been spending extra time with her trying to cheer her up, and we’ve been hitting the bars together more than usual. I’m single and casually dating, but would really like to find someone I connect with. Every time we hang out and have long chats where we talk about everything, a part of me feels like my roommate and I are so compatible it would be awesome if we could connect romantically. When she was drunk over the weekend she admitted she is attracted to me and it’s reignited my feelings for her. I am wondering whether it would be a good idea for us to hook up or if that would be the worst idea ever? We’re clearly both physically attracted to one another – I’m just not sure if she has feelings for me.
Your hookup could be the exception to the rule, but it’s generally a bad idea to hookup with your roommate and I really don’t think you should do it.
First, your roommate just got out of a long-term relationship and it sounds like she isn’t in any shape to make decisions about her love life. She only admitted to having feelings for you when she was drinking. If you drunkenly made out and fell asleep in the same bed, would she freak out in the morning? Is that something you want to find out?
Second, you keep asking if you should hook up with her but – as your letter made clear – you want something more than a hookup. You want a relationship.
Reading over your letter, your last line struck me: “I’m just not sure if she has feelings for me,” you write.
You two obviously work well as friends and roommates, and your casual question about a hookup is a thinly veiled effort to see if you can add sex to the equation and get the whole package from your roommate, who is currently grieving her breakup.
What your roommate needs is to get drunk and have a good cry with a trusted friend, or go out to the lesbian clubs and get hit on by sexy strangers. Your roommate needs to have a one-night stand or get back on the dating apps or have a terrible date then come home and binge watch the new season of OITNB.
She needs to put her ex behind her.
You do not want to be the person she does this with. Trust me.
Right now you’re buzzed on her admission of attraction to you. You’re zooming past all the what-ifs and focusing only on the possibility that you two could be a couple… or at least have some hot lesbian sex until either one of you finds your next partner.
That is a possible outcome, but it is ONE possible outcome out of many. Let me remind you of some alternate scenarios that could equally likely come to pass (trigger warning: buzzkill!).
You two hook up and the sex is terrible. You two hook up, then she gets back together with her ex and things get super awkward at your house super quickly. You have a few steamy makeout sessions, she tells you she wants to stop, and now you have to turn off the feelings faucet. You hook up, but you still have to carry her emotional baggage as she processes the breakup, so now you get hurt feelings wondering why she is so hung up on the ex when you’re giving her multiple orgasms a night. You have sex, it’s not what you hoped it would be, and now you have to tell her you don’t want to continue, crushing her feelings, giving her a self-esteem complex, and turning things toxic at home.
Bottom line: You two live together. If anything goes wrong, you’re stuck living together. Unless you want to find emergency housing, look for a subletter, break the least, potentially lose money, and probably lose the friendship.
If you were writing to say you two got drunk and confessed mutual attraction, and had both been single for a long while, this might be a different answer. But your roommate is not ready to date, and trying to convince her to have sex with you is not good for either one of you (also! you deserve a woman who can meet your needs and be a fully supportive partner! You don’t have to settle for a hookup with someone whose mind is on their ex, even if you’ve been single for a while).
If you can’t continue to be there with her without wanting to sleep with her, corral a mutual friend into playing the supportive bestie. Then get out there and look for women who you’re emotionally and sexually compatible with, and who are available.