What’s The Next Step With My Roommate?

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Dear Meredith,

I have developed deep feelings for one of my roommates. We have lived together for the last three months and spend nearly every day together. He is becoming a best friend, but a best friend I have serious feelings for. We are both single and neither one of us is dating. My friends who have seen us interact think he has feelings for me because of how he acts around me but up until recently, the moves he made weren’t big enough for me to let him know how I feel.

But things took an interesting turn last week. He told me he was jealous when I talked to another guy, we held hands walking home from going out, and he asked me to sleep in his bed with him to spoon.

I think the next time he does something like hold my hand or ask me to spoon I’m just gonna ask him what’s going on. But what if I tell him how I feel and he doesn’t feel the same way? Then I have to see him everyday. It would be too awkward for me. What should I do? Make the first move? Wait till he does?

– Lost in Love


Well, he certainly feels something. You’re spooning, after all.

My advice is more about when to ask him what’s happening. You don’t have to wait until he decides to hold your hand to have a conversation. If you have questions, ask. Maybe it’s better to bring all of this up when you’re not in bed holding hands. It might be a more thoughtful discussion if you’re in a less confusing place.

I’m sure you know that dating or even just hooking up with a roommate is dicey. If it doesn’t work out, you’ll have to look at him a lot. Also, if this turns out to be about casual feelings and hooking up when you/he feels like it, it might involve a lot of confusion and wondering.

But here’s the thing: I can’t tell you it’s not worth the risk. Many couples started as roommates. Also, living with someone is a great way to get to know them. This man sees you at your most casual and vulnerable. There’s something nice about knowing he’s attracted to that.

But again, this doesn’t have to be all about his moods. You can invite him to your room. You can have a talk when you’re ready. You can tell him how you feel. You can work your way to more spooning at your own pace.

– Meredith

Readers? What would your next steps be? Any thoughts on boundaries/concerns/ways to make this work?

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