Dear Prudence

Help! I’m in Love With My Roommate.

Dear Prudence answers more of your questions—only for Slate Plus members.

A woman looking flirtatiously toward a man.
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Every week, Daniel Mallory Ortberg answers additional questions from readers, just for Slate Plus members.

Q. I’m in love with my roommate: I recently moved in with two guys that I have mutual friends with. None of us knew each other before. I’ve been living there for about six months and I’ve started to grow strong feelings for one of them. He and I get along really well, and he’s often expressed how much he likes spending time with me and that we are “kindred spirits.” I frequently feel that he is flirting heavily with me and have had friends comment on it when they come over. However, he’s always dating a different girl and it’s becoming increasingly difficult not to get jealous. I want to tell him how I feel, but fear rejection and making the atmosphere in the apartment awkward. Should I tell him how I feel? Simply ask him out? Or just suppress the feelings for now as they might be caused by proximity?

A: It is difficult to ask someone out when you also live together, mostly because there’s no real way for the date to end. In the absolute best-case scenario where he likes you as much as you like him and has only been going out with different girls because he was convinced you’d never return his feelings, you’ve still got the very real problem of already having moved in together before getting to know one another romantically. That’s a lot of pressure for a first date! I think you have sufficient reason to think he might say yes if you asked him out, but unless you think everyone in the house would be comfortable with the two of you dating, I think you should wait until you have another living situation lined up before telling him how you feel. You say that you fear rejection, and I can’t imagine a rejection more stinging than having to share a bathroom with someone who just turned you down.