Dear Wendy
Dear Wendy

“Should I Tell My Roommate How I Feel About Her?”

Guest columnists and contributors are generously sharing their talents and insights while I’m taking some time to care for my new baby. Today’s letter is answered by columnist and blogger, Billie Criswell.

I’ve been living with my roommate for the past year and a half and so far I couldn’t find a better roommate. We just moved out of a group home and in to a 2-bedroom apartment a few months ago. For the past 6 to 8 months I’ve became very attracted to her and now that we’re living together I have grown to develop feelings to the point where I think about her all the time. We have a great relationship and chemistry. We IM constantly about random things and if we’re not IMing, we’re texting. We have so many things in common and enjoy each other’s company. If we’re home watching TV we have a great time; if we go out we have a great time.

Often, if she’s had a few drinks she becomes affectionate towards me. I did make a pass at her once but got rejected. This was when were lived in the group home. I’ve had mutual friends ask me if we we’re dating by the way we act towards each other. My concern is that there is a bit of an age difference — she’s 26 and I’m 39 — though that’s not a problem with me but for some people it is. Plus, it’s a roommate situation (I’ve dated a roommate before and when it went sour the living situation was very uncomfortable) and I don’t want to lose her as a friend if the feeling isn’t mutual. We once had a conversation about about how she hates it when guys don’t speak their mind about their feelings, and it’s killing me that that’s what I’m doing now. My question is: do tell her my how I’m feeling or let it go? — Crushing on the Roomie

As a person who has lived with dozens of roommates in my life, I have one hard and fast rule about them: no dating! Now, of course, there are always exceptions to every rule, but this doesn’t sound like one of them. Look, you may have a crush on the girl, but you sound like you are her BFF. There are no indications that she has any feelings for you and you said yourself that once you made a pass at her, but she turned you down. There is your answer.

It’s 2011, if this chick liked you, you would know. I doubt that she is harboring any unrequited feelings, and I think that you should put a lid on it and find a new love interest. It sounds like the two of you are great friends, and I think you need to keep it in the friend zone and not confuse love with convenience.

As for your conversation where she said she hates when guys don’t speak their minds, I’m sorry to say to you that you are reading too much into it. Obviously you are looking for a sign that makes you feel you can express your feelings, but I think it could potentially add a lot of weirdness to an otherwise great friendship.

My advice is that you look outside your home for someone suitable for you to date. Let it go with your roommate–she is one of many people you probably click with. If things change in the future, let her take the lead, but don’t hold out hope. Just enjoy the great friendship you already have with her and leave it at that.

* Billie Criswell is a columnist and blogger from the “Delaware Seashore.” She loves zumba, bloody marys, and cooking. You can follow her shenanigans at Bossyitalianwife.com.


27 comments… add one
  • FireStar November 25, 2011, 8:29 am

    I have no idea if the roommate is interested. The earlier rejection would suggest no. Maybe she likes things as is – knowing about your crush and just keeping you as her adoring fan. The situation sounds soul draining for you. Life is short. If you want to reap the rewards of life there is going to be an element of risk. Are you prepared to move on and find another roommate if things don’t work out the way you hope? Are you prepared to lose the friendship? Ready to move on to look for love somewhere else if she rejects you again? If so, then make your move. If not, then accept that you already suspect how it will play out and start focusing your attention where it will be appreciated. You are a grown man. It’s time to stop acting like a puppy.

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    • theattack November 25, 2011, 3:36 pm

      Am I the only one who assumed this was a woman writing in?

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      • FireStar November 25, 2011, 5:03 pm

        the letter said she hates it when guys don’t speak their mind – the implication is that he is a guy

      • caffeinatrix November 26, 2011, 2:47 am

        I thought it might be a female LW too, until I read the part about the roommate not liking guys who don’t speak their mind. Something about how it’s written, not sure how to explain it.

  • Will.i.am November 25, 2011, 8:58 am

    It’s a bit of a perfect situation for her. She’s gets all the stimulating conversation with you, but with none of the pressure for a relationship. Then, once she dates a guy that treats her wrong, she will be coming to you to cry on your shoulder.

    Like what was said earlier, if she wanted to be with you, you would know. You two live together so it wouldn’t be hard for her to show her feelings for you. Find someone else or risk losing a roommate and a good friend.

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  • MiMi November 25, 2011, 9:23 am

    LW, I’m sure the advice you’re hearing is not what you hoped but it does sound spot on.
    To protect yourself, when your roommate gets tipsy, go do your laundry or get out of there so you are not the unhappy recipient of her sloppy affection-that-doesn’t-mean-anything.
    Consider finding a new place to live – this life is no rehearsal and unrequited love never did anyone any good. You deserve better than to be toyed with.

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  • jess of citygirlsworld.com November 25, 2011, 9:39 am

    Exactly what Billie said!

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  • Jiggs November 25, 2011, 10:50 am

    She already told you what she felt when she rejected you earlier, even if she didn’t actually say the words “No, I’m not into it.” You’re also right about the awkward potential, except I think it’s going to get there even faster if/when you admit you want to date her. She’s clearly not interested, and she may (probably) be uncomfortable living with someone who wants more.

    Get out there and do some dating, and let this crush on your roommate die a natural death. It’s better for your living situation and since it’s unlikely you’ll get what you want anyway it’s better to preserve the friendship and move on.

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  • Allison November 25, 2011, 11:01 am

    Additionally, I’d consider a new living situation in the future if you’re unable to get over your feelings for her. Seeing someone every day who you can’t be with is rough. I think I’d also be slightly creeped out if my roommate harbored such strong feelings for me and I was unaware (more so if I was aware, though). But you seem to like the situation a lot (hopefully for more reasons than your crush), so as long as you work on moving on to someone else, you may be able to salvage it.

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  • Carolynasaurus November 25, 2011, 11:06 am

    There are a couple of options I think you have:

    1) Make a pass at her again when you live with her. Odds are she’ll reject you again and it’ll just make things hella awkward and potentially ruin your friendship.
    2) Start dating someone new. I would put good money on her getting jealous that someone else is getting all your attention and trying to win you over. You break up with the other girl, the roommate gets bored because the chase is over, and things fizzle out.
    3) You move out of the house, hoping the friendship can develop into something more. However, without the close proximity, she lets things fizzle with you.
    4) You still live together and nothing changes.

    I know these are mainly worst case scenarios, but there’s not exactly a best case scenario, is there? Think things through, but I’m sorry, I can’t imagine things going too well here.

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  • McLovin November 25, 2011, 11:12 am

    I’d leave it alone. She sees you as a trusted friend and has already set boundaries, even without actually stating them. And who doesn’t get affectionate when they drink?

    If you can set aside your “crush” then remain roommates, but spend more time with other people. Don’t make this awkward for both of you.

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  • atraditionalist November 25, 2011, 12:08 pm

    I’m going to be the bad guy here and say that you need to move out of the house. Not just for the sake of not being awkward but also because you are 39 years old and it’s time to not live with roomates anymore. I know for myself that would be something that I would find unattractive in a man – but then again I’m old fashioned.

    Anyways if you move out it could give her the chance to not just see you as a roomate and show that you are able to support yourself in your own place. And if that changes nothing then you’d at least avoid having those feelings thrown in your face when a new guy stays the night in her room.

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    • theattack November 25, 2011, 3:53 pm

      Considering the LW just got out of a group home, having a roommate may not be something he can just choose not to have. Group homes are often for people who have a difficult time finding housing, or who cannot live alone for some medical or psychological reason. It sounds like he’s done a good job finding what he’s got. Leaving that situation may place him at harm, or he may not be able to get other housing.

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      • ele4phant November 26, 2011, 3:32 pm

        Oh, I didn’t catch the group home thing, I just assumed he meant they had lived in a house with multiple other people before moving down to an two bedroom apartment.

      • theattack November 26, 2011, 3:42 pm

        Yeah, I can definitely see how most people would probably read it that way. Since I’m an almost-social worker (just a few months left to go!), those sorts of things stand out to me.

  • cdubs November 25, 2011, 12:14 pm

    I don’t know. Just because there was an earlier rejection doesn’t mean something couldn’t happen in the future (especially since she gets affectionate when drinking). My college boyfriend liked me a lot when we first met, but I wasn’t interested that way. But I kept hanging out with him because we got along, despite the fact that I knew he liked me and wanted to date. As we hung out more, I did develop feelings for him, and we ended up dating for a year and a half. Not saying this is necessarily the case here, and she might just look at you as a friend (not trying to give you false hope). But just because you get rejected once doesn’t mean it will be like that forever.

    I would say, if you’re feeling brave, find another possible living situation. Then, when you have your Plan B in place, let her know how you feel. It’s obvioulsy making you miserable just being friends, so you might as well get it out now, before it instead blows up into a mess one day when you can’t take it anymore (and maybe have had a few drinks – I know I tend to be WAY more honest when I’ve been drinking…). And that spells disaster. Better to tell her on your own terms, when you’re calm, and it hasn’t built up anymore.

    Then, if she rejects you, be polite, be an adult, and let her know that you understand, and you respect her decision, but you’re sorry, you don’t think you can be friends (or roommates) anymore, and move out. (Although you should be prepared to still have to pay your half of the rent. Obligations you know! So maybe you should wait until the two of you are thinking about renewing your lease..)

    Short version: go for it, but make sure you have a backup living situation.

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    • ele4phant November 26, 2011, 3:38 pm

      I don’t disagree that just because a rejection happens earlier doesn’t mean everything is shot forever. However, he made the pass last time, the ball is in her court now. She is aware he’s interested, if she reciprocates that then she should be the one to make that clear.

      IMO, he shouldn’t make another pass, but instead wait for when and if she returns his interest. There’s nothing worse than the guy who repeatedly hits on you despite the fact you’ve made it clear you’re not interested. I can’t imagine what it would be like to have that guy be your roommate. If she’s interested, she knows where to find him.

      Perhaps he should look for another place to live though. If its difficult for him to be near her but not be with her, it may be in the best interest of his mental health to not be with her all the time.

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  • Skyblossom November 25, 2011, 12:22 pm

    I think you need to spend less time texting and IMing with your roommate because that’s keeping your emotions focused on her. Remain friends but don’t let the friendship drown out your chances of a real relationship with a woman whose interested in you. Take the time you’re devoting to her down from an infatuation level to a friendship level.

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  • Will.i.am November 25, 2011, 12:26 pm

    Having a roommate near 40 that isn’t your girlfriend, wife, or child is a bit odd. After college, men and women don’t find the living at home situation very attractive. When I moved out I thought about having a roommate, but then I realized entertaining guest and having dates would be difficult.

    Sometimes, you just want to have that privacy to do what you want. Even if your roommate was to leave, they could come back home at anytime, since they are most likely on the lease with you. I agree with the commentor, and maybe it’s time for you to find a one bedroom to yourself.

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    • LSS86 November 28, 2011, 1:08 pm

      They were previously living in a group home, which suggests that they are perhaps not capable of living on their own. Though I do find it very interesting that a male/female pairing could leave a group home and live together. Group homes usually have case managers who serve as sort of life coaches/aides for their residents, and I can’t imagine that the case managers would be too thrilled about the two of them living together when they’re not in a relationship.

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  • Painted_lady November 25, 2011, 2:04 pm

    So your roommate shot you down when you made a move, and yet you think you might still have a chance. You admit it’s gone really badly before when you’ve dated roommates, and yet you still think you should go for it. Have you heard Einstein’s definition of insanity as doing the same thing over and over, expecting different results? Right now you’re two for two, friend.

    First off, your roommate TOLD YOU NO. She did it in a way that indicates she was trying not to embarrass you or she isn’t assertive enough to be unequivocal in her refusal, but she did. You made a move, she shot you down. I realize many women play hard to get, but this isn’t one of those situations. She sees you as a friend – a nice, asexual friend. She may enjoy that you’re attracted to her, but she also enjoys that you have respected her right not to be attracted back. If you press the issue, what you are saying is, “I don’t believe you know your own mind, and I believe I know better than you that you’re attracted to me.” This is incredibly disrespectful, no matter what Hollywood would have you believe. Many women are bad at “No” for many reasons, and we need to get better at it, but many men also need to get better at hearing it. You are one of them. She’s told you no, and if you didn’t hear it the first time, you can be damn sure she’s going to say it in a way you can hear it the next time, and it will end badly between you as roommates. Again. Or you could just learn from what’s already happened.

    Also, if you’re a dude past 30 and you’ve still got a roommate? That’s weird. Every male I’ve known – my ex included in this – who has a roommate always has this incredibly bizarre dynamic with said roommate. Male or female, there’s always this either parental or romantic vibe that reads to me, no matter the gender of the roommate, like one person needs to be told what to do, and one person needs to do the telling. And no romantic partner coming from the outside is going to feel comfortable or welcome in that environment. If the roommates are straight and opposite sex, it’s worse. So you’ve basically ensured that you and your roommate are each other’s only romantic prospects. And then you wonder why the dynamic is so fraught.

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    • Painted_lady November 25, 2011, 2:30 pm

      Actually, I occasionally joke to people who know my ex and his roommate that I was the “other woman” in their relationship – even though the roommate was straight and male. Everyone who knows the two of them completely agrees. I guess I shouldn’t be surprised that neither of them has had a relationship since The Vegan and I broke up two years ago. And everyone knows by now the situation with my roommate and her boyfriend, but a huge part of why I was moving out anyway is because my boyfriend is moving here and it’s too hard to have a long-term relationship as an adult when you live with someone else.

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  • theattack November 25, 2011, 3:50 pm

    LW, You said you just got out of a group home and now you are living with one of the girls there. This makes me assume that your living situation may be something you worked hard to get, and it may be one of your few options. I’m not sure what sort of group home you were in, and what qualified you for that program. But it sounds like you really need this housing. In a normal situation, I would consider “going for it” as a possibility (albeit a bad one). Do not give up what progress you’ve made toward stable housing and a supportive friendship over a crush. Try to set your crush aside and just focus on your roommate relationship with her. Find some other friends so you’re not spending so much time with her. And stop IM-ing her and texting her all the time! That’s only making this worse for you. If you feel that you cannot live with her without these feelings growing and pestering you, then first find another place to live. You can pursue a relationship with her after you’re not living together. But this is risky, as housing may not be something that comes easily to you. Do not consider this option lightly.

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    • LSS86 November 28, 2011, 1:10 pm

      Agreed wholeheartedly. I would also suggest talking to someone from the group home about finding a different living situation if it’s too much to bear living with someone you have feelings for. Just because you’re not living there anymore doesn’t mean they don’t still have your best interests at heart. They might be able to help you find a more comfortable living situation.

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    • William Lyons November 29, 2011, 4:49 pm

      You need to dramatically reduce the time you spend with and talking to her. She is using you as a backup / non-sexual boyfriend because you are always available and she knows you harbor feelings for her. Trust me, I’ve been there. Most people don’t have it work out like it did for me. If you pull back one of two things will happen: 1) She gets jealous and annoyed and tries to get back more of your attention (This doesn’t mean she necessarily has feelings for you). or 2) She won’t care and that will show you she definitely doesn’t have feelings for you.

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  • caffeinatrix November 26, 2011, 3:09 am

    I think Billie is right on here. I hate to echo the sentiment, dude, but it sounds like she is not into you like that. I might even venture a guess that she already knows how you feel about her, since she’s shot you down before. So, she knows that there’d be no risk in confessing her feelings to you- the problem is, she has none. She likes the attention, sure, but she’s not interested in dating you.
    Do not pursue her. Do not tell her how you feel. Focus on other friends or throw yourself into a hobby to distract yourself, and quit talking to her so much when you’re not at home. There are plenty of other people out there to date. Hell, sometimes dating is easier than finding a roommate you actually enjoy living with, so why would you go screwing that up?

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    • theattack November 26, 2011, 3:39 pm

      I very much second your last statement!!! So much. So. So. So. Much. Having a good living situation is one of the most important things to have. It took me years to find someone I could even tolerate living with. The boyfriends are not that difficult to find.

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