Dear Wendy
Dear Wendy

“I’m Falling for My Roommate!”

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I know that when I made the decision to allow an extremely attractive stranger to live with me I was taking a dangerous step. But he had a girlfriend at the time, so I thought I was safe…except about three weeks later they broke up. I have now been living with my roommate for nine months, and slowly we have grown closer as friends. It wasn’t until around Christmas time that my roommate went very out of his way to make life easier on me when my car broke down. Soon after, we were having lunch together almost every day (we worked near each other at the time) and then we would hang out at night, watching movies and drinking together.

After he came back from Christmas break, I realized I had a problem — I was totally falling for him. I tried to ignore it, but the more we hung out together, and the more he casually touched my hand or lower back, the more I couldn’t stop from thinking about him. We have cuddled on the couch a couple times, and sometimes he gives me random hugs. Things really progressed in a different direction last week when I was having bad cramps and he came into my room to see if I was ok. Not only did he climb into bed next to me, but he also talked to me to help make me feel better. About an hour later, I was feeling better, and I wanted him to know I appreciated him, so I kissed him. He reciprocated, but also pulled back and said, “We shouldn’t be doing this.” I immediately conceded and lay back down on his shoulder. I felt better, I felt comfortable, and I drifted off to sleep. Maybe it was a few minutes or an hour later, but I suddenly noticed his heart rate speeding up, his hands were all over my skin and in my hair, and when I leaned my head back to say something, he practically attacked me. We made out like our lives depended on it!! It felt amazing….until he pulled back. He said he didn’t think this was a good idea. I asked him if it would be different if we weren’t roommates and he said yes, but that he loves the friendship we have and doesn’t want to ruin anything.

Over the last couple days I’ve tried to show him that we can be normal and can remain friends, and for the most part things aren’t weird. We even cuddled on the couch watching a movie since the kiss. My question to you would be how do I know he is interested in me as more than friends? I wouldn’t make a move again if I didn’t think he was interested. Right now he seems more scared to lose what we have. How do I show him there is no need to be scared? I hope in some way you could shed some light on my crazy situation. — Falling for Roomie

It’s really not that crazy a situation, to be honest. You are two young, single people who enjoy each other’s company and are attracted to each other and can’t decide whether the temptation to take things to the next level is worth the risk to your friendship and your roommate situation. But the decision has already been made for you. You HAVE taken things to the next level, and you are fooling yourselves if you think you can just rewind now and pretend that your attraction to each other doesn’t exist and that the make-out session between you never happened and that the feelings you have aren’t really there. They’re there. And neither one of you seems capable of keeping things at a strictly platonic level or there wouldn’t be cuddling on the couch and kisses in bed and so forth.

So, what do you do now? You have four options: 1) Continue living with each other but avoid having a relationship; 2) Continue living together and start a relationship; 3) Stop living together and continue your friendship; 4) Stop living together and try dating. I can tell you right away that option 1 will not work. You won’t be able to avoid being intimate with each other…at least not without a mad amount of frustration and jealousy. What happens when one of you starts dating someone else? What happens when he brings a girl home or you bring home a guy? (It’s not going to be good). You might have better luck with option 2, but talk about pressure. What happens if you decide you aren’t good as romantic partners? Or, what happens if one person falls in love but the other doesn’t? What happens if it’s a messy breakup? Or, what if you simply need a little distance from each other (and you will)? It’s not like you’ll be able to just go home to get away for a while.

If it were I, I’d go with option 3 or 4. (I’d probably try option 4!). I think you should ask him to move out, find a new roommate (someone there is no possibility of you being attracted to or wanting to date) and go from there. He might be inconvenienced, but I’ll bet he’ll be more relieved than anything, and so will you. If you really like each other, you’ll continue to make time for one another and the time you’ll have together will be more special because it won’t be this whole, awkward “we shouldn’t be doing this…” thing. Then again, it may turn out that the real appeal to your attraction has been the idea that it’s forbidden and, once it’s no longer forbidden, it won’t be all that hot anymore. In that case, you’ll hopefully still get a great friend out of the equation and you won’t have to worry about your roommate bringing home a date you wish could be you.


You can follow me on Facebook here and Twitter here.

If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.

33 comments… add one
  • Morgan March 27, 2014, 9:15 am

    Oh, Oh, I know this one! Well, sort of. My bff recently started dating her roommate. Like you it was a random roommate situation, and it kind of started similarly (bad day, one crawls into bed, rest is history). They went with option 2, and it’s working so far, but obviously if it goes bad that would be…bad. My advice is not to do what they are doing (I think right now they are planning on not living together when the lease is up, but I’m not sure. But I agree with Wendy, one of you should move out if only because your relationship doesn’t need that kind of pressure right at the beginning, of making the relationship work and the living situation work and it has to be perfect or else everything will be ruined. Maybe you’ll start dating, discover you’re better as friends, and that will just happen organically. But with the added pressure of it having to work because of the living situation, you might fight the fact that it isn’t meant to be and ruin that friendship as well.

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    • RedroverRedrover March 27, 2014, 7:20 pm


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  • SasLinna March 27, 2014, 9:21 am

    I think you should lay your cards on the table and tell him you want to date him. (That’s what you want, right?). Just admit to him that you don’t think you can go back to being just friends and see how he reacts. If he has an interest in dating you I think he’ll be happy to move out. If he doesn’t want to lose the roommate situation and really just wants to be friends – you’re still going to have to ask him to move out. But at least you’ll know what your situation is and you’ll be able to move on. And please… don’t take the route of sometimes cuddling with him on the couch hoping that you can eventually convert your roommate into a boyfriend. That won’t work.

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  • Jaq Attack March 27, 2014, 9:27 am

    Well my boyfriend and I have been together for 3 years and we started out as……. Roommates!
    We lived together for the summer, started dating, so then I got my own place one town over. We did that for about 7 months, decided it was a pain, so we’ve been living together since.

    I think it’s important to have your own space for a period of time while the relationship is developing. You need to have you time – it’s hard to start a new relationship AND have to be around them all the time. Where will you have girl time to talk about him??

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  • Lindsay March 27, 2014, 9:27 am

    I like Wendy’s suggestions. Aside from the idea that forbidden fruit is tempting, sometimes people just get interested in each other because they’re there. Roommate and other situations sometimes put you with people that you’d never otherwise be friends with, and then suddenly you’re there, and it’s like, hey, this is easy to start. I actually almost got involved with a roommate for this reason, and I’m glad I didn’t. So, it’d be nice before you went down this road to see if he’s someone that you’d actually want to date otherwise, and vice versa. (You also don’t want to find out that he’s interested in you just because you were a girl in a bed who was kissing him.) And you also want to make perfectly clear that he means it when he says his hesitation is that you’re roommates. I know this all sounds really cynical, but you know.

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    • SasLinna March 27, 2014, 9:48 am

      I’m with you. I think “we’re roommates, so we have to stop this” is a pretty bad argument because they could stop being roommates quite easily. The argument against getting involved with roommates only really holds water when you haven’t yet started being involved. Once you’ve already made out etc. if the roommate continues repeating this he’s probably not that into her.

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  • Lolabeans March 27, 2014, 9:29 am

    That was like reading a YA novel!

    Go with option 4.

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    • lets_be_honest March 27, 2014, 10:48 am

      And I loved every minute of it!

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  • LlamaPajamas March 27, 2014, 9:45 am

    This is such a sweet, straightforward problem! LW, your roomie sounds like a great guy – you know he’s sweet, thoughtful, and a great friend. I think you need to talk to him about moving out regardless of whether or not you end up dating, but I’d definitely let him know you’d like a relationship. Good luck!

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    • j2 March 27, 2014, 10:05 am

      Yes, a refreshing change!

      It might help to know the ages, though the “Christmas break” phrase seems to imply college age.

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  • rosie posie March 27, 2014, 10:00 am

    I agree with Wendy. Option 4. Without any spoilers for people who may watch the show it was absolutely brilliant of Wendy to use a pic of Nick and Jess from New Girl.

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    • GatorGirl March 27, 2014, 10:02 am

      Man I love that show.

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      • rosie posie March 27, 2014, 10:24 am

        Me too! My love for Schmidt is so strong! There hasn’t been enough of his douchiness lately.

      • LlamaPajamas March 27, 2014, 11:44 am

        I love Schmidt. I want to watch New Girl and write him poetry with my body all day every day.

      • GatorGirl March 27, 2014, 11:50 am

        I’m so glad they brought Coach back, but I think Winston is my favorite. And that cat!

  • muchachaenlaventana March 27, 2014, 10:01 am

    I know a few people who have done this. I don’t really see what is so bad about it. I mean you have already been living together a good deal, your lease is probably up soon. Why not date and then each move out into respective new places (or not, whatever) and see where it goes.

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    • SasLinna March 27, 2014, 10:27 am

      Yes, it’s totally fine and I know of cases where it’s worked out! The only problem is that so far he doesn’t seem to be on board. Which is why I think she should be more explicit and let him know what she wants. Otherwise they’ll just have weird friendship with unclear boundaries.

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      • muchachaenlaventana March 27, 2014, 10:47 am

        Yeah I agree, I sort of only skimmed the letter but definitely if he is not on board than my advice holds no water.

  • bethany March 27, 2014, 10:17 am

    I like options 2 and 4, depending on how much time is left on your lease. Say your lease ends in June? Then go for it, and just don’t renew the lease and look for separate places. Say your lease ends in Feb 2015? See if one of you can sublet your room and move out.

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  • No Pants March 27, 2014, 10:22 am

    My friend ended up marrying her roommate, so you never know! Go for it.

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  • peachy March 27, 2014, 10:39 am

    I don’t like the part where he pulls back when it’s face to face, but gets carried away and puts his hands on her while she’s asleep (I think that’s what it said). Mixed Message Borderline Creeper Dude has got to go.

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    • GatorGirl March 27, 2014, 11:06 am

      YES! I kinda stopped reading at the “drifted off to sleep…woke up to his hands all over me” part. That’s cree-pyyyyyy. (Disclaimer: if there is a precedent set where waking the other up while loving on them is accepted/encourage- totes cool. But that’s not this situation.) How far would it have gone if she hadn’t woken up?? Eck.

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    • LlamaPajamas March 27, 2014, 11:43 am

      I picked up on this too (the “practically attacked me” part really bothered me) but decided to ignore it in the hopes that she was just trying to convey their level of passion. I’m always crying “rape culture” (IRL, not on here) and didn’t want to be that girl today, but I’ll still give the LW a bit of big-sisterly advice: consent is cool! Being snuggled up in bed with someone doesn’t mean they have the right to grope you or do anything that you’re not comfortable with. You can stop at any time! Pay attention when a guy will do this while you’re sleeping but not while you’re awake. I’m not saying anything bad happened here, just be alert. Always be alert!
      This post brought to you by the uber-feminist LP who taught sex ed in college but still didn’t know how to set boundaries in her own sexual relationships until her late 20s and really regrets that.

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      • lets_be_honest March 27, 2014, 11:53 am

        That’s how I read it too (saying attacked as trying to describe a level of passion).

    • lets_be_honest March 27, 2014, 11:48 am

      I read it as though she woke up from his heart racing and then it happened, obviously could be wrong though.

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      • GatorGirl March 27, 2014, 11:49 am

        How does a racing heart wake another person up though?

      • lets_be_honest March 27, 2014, 11:51 am

        Well, she’s just saying some time after falling asleep, she noticed his heart was racing, so not that that “noise” woke her up, but she must’ve been awake in order to notice a racing heart beat. Right?

      • GatorGirl March 27, 2014, 12:00 pm

        Yeah, I mean it could go either way…a passionate make out session that started spontaneously or a creeper feeling her up while she sleeps. With out clarification I’m a little sketched out.

      • Banana March 27, 2014, 12:41 pm

        If he’s secretly a robot and he has a mechanical heart. LW, DON’T DATE A ROBOT, IT WILL NEVER WORK OUT BETWEEN YOU!

  • othy March 27, 2014, 11:16 am

    My brother and SIL started out as roommates. They lived in a big house with about a million other people. But they tried option 2, and it worked. They moved in to a place with just the two of them after about a year of dating. They’ve been happily married for 4 years now.

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  • fast eddie March 27, 2014, 10:49 am

    Why not go with the flow and enjoy each other. If it doesn’t work out, no matter how that evolves, you can always move or find another roommate. Life is too short for regrets.

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    • Anonymous July 27, 2020, 5:04 pm

      Yep!! My sentiments because life is too short. Seize the day!

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  • Jamaymay April 24, 2017, 1:14 am

    This thread has been so helpful. A guy I used to work with and who I thought was cute back in the day recently moved in and or paths haven’t crossed yet, but I’m already getting the sense that I’m going to be attaracted to him and be interested in dating him. He’s tall, smart, cute, outdoorsy, has a good career, super nice, considerate… what’s not to like? I’m so grateful for the 4 option breakdown. I’m all for clear communication and boundaries but am also open to a little magic. I’m going to proceed with transparency and the move-out option #4 is mg favorite. If I like him and we’re into each other and he moves out, we can date, fall in love and perhaps someday he can move back in. No need to freak out about this now after having read this, so thanks ya’ll. 🙂

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