I really really like him. But should I tell him?
January 11, 2012 7:42 PM   Subscribe

I have a crush on my brother's roommate. I was going to tell him this, but...

...there are some complications that have made me hesitate. Please help me sort out my feelings!

This person has been living with my brother for the past four years. He moved into my brother's apartment shortly after I moved to another state for college. I've gotten to know him during my return visits, and I really, really like this guy. He's very warm, friendly, and funny. His amiable nature swept me off my feet, made me feel important, and in my heart of hearts, led me to maybe maybe maybe think that there was a chance he's interested. But I've always been careful to counter the giddy feelings he inspires by reasoning that he's just naturally friendly. He's also six years older than I, so it's possible that he feels enough of an age difference that he wouldn't want to date me.

Previously, I never even allowed myself to consider the possibility of telling him, since he is my brother's and occasionally my roommate. But a male acquaintance of mine has recently been sending mixed signals, and even though I personally wouldn't date him I've thought about what an ego-boost it would be if it turned out that he did like me (I have low self-esteem issues, and I have never dated because I am so shy). That led me to think that maybe I should let my crush know I like him, just to give him an ego-boost (although unlike my self-esteem, his is intact and healthy--but not in an arrogant way) while emphasizing that I'm only doing it to let him know what a great person he is, and not because I think there's a chance for us.

But I recently graduated college, and depending on how my job search turns out, I may be living with my bro and his roommate on a more permanent basis. So one problem that initially made me hesitate when considering whether to tell him was the awkwardness of revealing my feelings to someone whom I may have to see every day in the near future.

Something else that is making me hesitate is recent developments. My new resolve to tell him stemmed from my New Years' resolution to address my fears/do that which I've always thought I couldn't. In a brilliant stroke of bad timing, he recently met someone whom he really likes, although his feelings are unrequited for reasons I won't go into for the sake of privacy. I was crestfallen when I found this out, and it's completely shattered my preconceived notion that I could be unselfishly happy for him once he does start dating someone again. For some reason, the idea of telling him now is completely and utterly mortifying, and I cannot for the life of me figure out why. I suppose it may be because, before he met this girl, in spite of all my dogged rationalizing that he was just being nice, I still allowed myself the teensiest, tiniest hope that maybe all his friendly gestures were signs that he was in to me, and my motivation for telling him to make him feel good was all just a ruse created by the rational side of me to cover up the hopefulness stirred up by my emotional side. But right now, I'm wondering if this embarrassment is some manifestation of the fear that I'm trying to address. I've thought about this and thought about this until I'm not sure whether my emotions are valid, considering the circumstances. Is my embarrassment at the thought of telling him warranted? Or am I letting fear dictate my actions in some way that I don't consciously realize? Would there be any benefit at all in confessing my feelings? Throughout the entire week I've been considering this, my gut inclination was that I shouldn't do it. If I were to confess, it seems like the best time to do so would be when either he or I move out (though the former would probably be the best situation), so that we could avoid any repercussions of awkwardness from living together. But I don't know. I need someone with more insight/dating/unrequited crush experience to give me some advice on this.

Furthermore, how should I go about getting over my crush? Obviously, the best answer would be to move somewhere else, but in the meantime, until that can happen, how should I go about un-crushing? I've tried staying in my room to avoid him but it makes me sad if I miss opportunities to talk to him. We're close enough to the point that I may offend him if I stopped conversing with him or acted distantly toward him. I feel as if this crush is ruining the concept of home for me, because I now associate it with him, and I can't draw the same sense of comfort from home as I could if he were absent. I realize that I have to just enjoy being home because it's home, but it's hard when one of the things I look forward to most when the pleasure I get from my visits are largely dependent on how much I interact with him. Do you have any advice for me, MeFites?
posted by dean_deen to Human Relations (17 answers total) 1 user marked this as a favorite
Don't tell him until you know you're not moving in with him and your brother. I literally cannot think of a more awkward situation to find yourself in, even if it turns out he likes you back and you guys start dating.

As to how to get over it - meet someone else. Or at least try to interact with more people and "move on" emotionally. This isn't to say you have to snub the guy, just develop a social life that doesn't always include him. Don't depend on him for every little thing. This, and time, will enable you to move on.

Or wait till you're not living with him, and then just tell him.
posted by Sara C. at 7:48 PM on January 11, 2012 [2 favorites]

I wouldn't let your new resolution force you into sharing your feelings at an inappropriate time. You seem to think the timing is not right now, which may be the case. If you think that's true, then hold off. If you think that's just an excuse to avoid telling him your feelings, then go for it.

If down the road you think you may regret not telling him at some point, then you should tell him. You seem to indicate some regret at not having said anything already since you are disappointed he recently became fond of someone else.

If you tell him and he isn't on board, then you will be free to move on. The awkwardness won't last long unless you perpetuate your own unrequited feelings. So maybe if you tell yourself, "If the answer is no, then I'll accept that and move on" then you'll at least be somewhat prepared to deal with the negative aftermath. However, if the answer is positive, then you have lots to look forward to.
posted by thorny at 7:53 PM on January 11, 2012

Confessions of feelings are awkward. How is anyone supposed to respond to that?

I think you need to jump into dating, as in, go on some dates. As a general rule, if you want to date someone, I'm a fan of asking them on a date -- that's a concrete thing that they can either say yes they will do or no they will not.

But in this particular situation, the timing is lousy. He's hardcore crushing on someone else AND you might be living with him and your brother for the foreseeable future -- not a winning combination. Give it some time. When that's all resolved, then, if you want, ask him on a date.
posted by J. Wilson at 8:22 PM on January 11, 2012 [1 favorite]

If you do move in with your brother, starting a relationship with somebody you're already living with could cause the relationship to move much faster than would otherwise be healthy.

Make sure you aren't going to live with him before you admit any feelings. Then your relationship will have the healthy start it deserves. Don't go and sabotage things from the get-go!

Also, after you've lived with the guy as a roommate for awhile your feelings may change. Seeing somebody day in and day out leaves lots of chances for their true selves to show up. For all you know this guy could only shower when guests are coming! He might wear the same clothes for weeks! He might use a spoon and then put it back in the drawer! I'm just making stuff up, but I hope you get the idea.
posted by TooFewShoes at 8:24 PM on January 11, 2012 [3 favorites]

the thing about self-revelations that you learn after you've struggled through a few of them is that they're not actually turning points, or transformative experiences, and they don't make you feel less afraid or more mature. they're just whatever they are - either awkward or cool, depending. so don't pressure yourself into doing it because you think it would be cowardice not to - it's not. my opinion is that you should go find some other cool people to hang out with - you are banging on a closed door here. another cool thing you will find out as you go through life is that there are a *ton* of cool, interesting people out there
posted by facetious at 9:57 PM on January 11, 2012 [6 favorites]

Please do not over-analyze your feelings - I don't mean this in a snarky way and hoping it comes across as a humble request to you. But as J.Wilson mentions, the timing's a bit off, considering so much "interesting" is happening to you both.

Once you have moved in and he has moved on, see if you are still attracted to him and then ask him out for a date. Sometimes, the mere thought that someone is attracted to us can be a tremendous ego-booster and can make us miss signs about a different outcome.

In case he is still hurt and does not want to go out now, saying no to you may be tough for him (he may be on rebound from the feeling that he understands how rejection can cause pain) and even if he does, it maybe awkward for you both to be room mates later.
posted by theobserver at 10:01 PM on January 11, 2012

Most of what I had reason to regret in my life has been the times I suspected that with a little courage and risk I might have gained something of value, but because of my fear I let the opportunity slip by.

There is no such thing as a perfect time to take a risk -- that's in the nature of a risk. You may wish to minimize your risk; certainly when you are moving in with this guy at a time he is crushing on someone else may not be the best time to express your feelings. On the other hand, it is amazing how quickly such opportunities are lost. Today is not a good day; tomorrow it simply isn't possible anymore because he's moved on to someone or something else.

Am I saying just go for it? Not quite. But I am say that regretting your own cowardice is a bitter, bitter thing.
posted by driley at 1:33 AM on January 12, 2012 [1 favorite]

But I recently graduated college, and depending on how my job search turns out, I may be living with my bro and his roommate on a more permanent basis.

If you really are serious about him, do not move into the house, no matter how convenient it is, because inevitably you're either going to:

1) Tell him and he says no and make it weird for you and him and possibly your brother;
2) Tell him and he says yes and then it's uber-weird for your brother (because he'll be living in the house his sister is getting...intimate in...not to mention, for a lot of people they don't want to live with a couple, so you'll be foisting that on him);
3) Don't tell him and watch him start dating someone else.

Seriously. Get out of the house first and on your own before you do anything.
posted by Rodrigo Lamaitre at 4:37 AM on January 12, 2012 [2 favorites]

Get your own place, then ask him out.

I'm about 99.9% sure that those are the right choices.

Also, 6 years is not really a huge difference, as long as you're old enough to drink.
posted by empath at 7:09 AM on January 12, 2012 [1 favorite]

Don't take the fact that he's crushing on somebody else as an indication that he never was into you. It's perfectly possible to be consistently low-grade interested in someone for 4 years, while intermittently dating someone else, especially if there's practical reasons against the one, and the other is convenient. I'm not saying you need to nurture the idea that you two are meant to be together, just saying that the logic is not there.

My advice: don't tell him. Try not to dwell on it. Be excited that you're starting a new year, with two roommates you enjoy spending time with, and take this opportunity to get to know him even better. There is such a thing a nurturing a crush - letting your mind wander, letting the castles in the air build, reading subtext into everything he says and does, gossiping with friends over whether he really meant X when he said Y, etc. Try very hard not to do that. You'll make your life miserable, you'll probably make him nervous, cause all sorts of tensions, etc. But if you can decide that you're just going to enjoy living with him and get mad when he doesn't wash his dishes and treat him like you would any roommate, eventually you'll be in a position that you can move out and start treating this like a normal person to ask out.

The smart but expensive option: plan on not living with them. Tell him it doesn't seem like a good idea because you've been interested in him for a while and it would just be too complicated. Get an apartment in the same part of town but at least 5 blocks away. Of course, if you don't have a job yet, this'll be complicated.

The dream-world option: There are scenarios in which this could work out, you and him as a couple living with your brother, but it all depends on the personalities involved, esp your brother. As well as, of course, whether you two would be a good couple. If life were a sitcom (hint: it isn't) you'd spend years avoiding any mention of a crush, and then it would turn out it had been reciprocated all along. This should be avoided. The best way to do this is to, while talking with your brother, mention that you like him. Or better yet "liked" him, takes the tension off even if the past tense not entirely true.
"Say, Bro, I really do appreciate that you're willing to have me live with you and John. I know the two of you have been happy in that house and I hope having three people doesn't make it seem too small. I'll try to be a good roommate. It's so great to have a place to live taken care of. But right now I'm thinking that once I get a job and get things settled, I'm pretty likely to want to get a place of my own... Yeah, it's not you, really... This is embarassing to admit but I don't want things to be awkward since I kind of liked John. I know he's all over the moon about Sally right now, and I'm not carrying a torch for him or anything, but there's part of the idea of living with you guys that feels a bit weird. So maybe it's a good thing if this isn't a long-term living plan."
Now you've told your brother, he knows John much better than you do, he can decide if he likes the idea of living with you two as a couple, or if he likes John as a buddy but wouldn't want his sister dating, he may tell you that, or he may just chuckle and say, deal with it. But that means that if there are weird undercurrents, he'll know what's going on, and if there's a chance at requitedness or a definite non-requitedness he'd be in a position to let you know. So if you trust your brother, talk to him.
posted by aimedwander at 7:18 AM on January 12, 2012 [1 favorite]

That led me to think that maybe I should let my crush know I like him, just to give him an ego-boost (although unlike my self-esteem, his is intact and healthy--but not in an arrogant way) while emphasizing that I'm only doing it to let him know what a great person he is, and not because I think there's a chance for us.

my motivation for telling him to make him feel good was all just a ruse created by the rational side of me to cover up the hopefulness stirred up by my emotional side.

I think your self-analysis is spot-on here. Honestly, if someone came up to me more or less out-of-the-blue and said, "I think you're funny and hot and smart and I totally have a crush on you but I SWEAR I'M ONLY TELLING YOU THIS ON GENERAL PRINCIPLE AND I HAVE NO INTEREST OR HOPE IN DATING YOU REALLY I SWEAR" my first reaction would be, "Yeah, right, sure you're not interested," and my second would be, "That's a weirdly awkward passive-aggressive way to ask me out."

So, yeah, if/when you admit your crush, be honest with him and yourself, you're admitting it because you're hoping to be more than friends.

I wouldn't worry too much about the whole "he's got his own unrequited crush on another girl" situation. In the first place, that's totally, utterly normal SOP Relationship Drama for the under 30 crowd. Just because he likes somebody, doesn't mean he wouldn't be interested in dating you. In the second place, there's really nothing you can do about his relationship (or lack thereof) with this other girl - it's between the two of them. Yeah, it'll suck if he winds up with her without knowing how you feel about him, but, well, that's life. You have to learn how to deal with the fact that things often don't work out how you hoped they would.

Rodrigo makes some excellent points above. You should listen to him. Not least because it's really really true that the only "cure" for an unrequited crush is time and distance, and you are correct in guessing that it'll be so much harder to get over the guy if it doesn't work out when you're living with him.

We're close enough to the point that I may offend him if I stopped conversing with him or acted distantly toward him.

You have to take a deep breath and realize that just being in your own head and analyzing your own behavior can skew your perceptions of that behavior. Most people are nowhere near as hyper-aware of your behavior as you are. There is definitely LOTS of room for you to distance yourself from him without shutting him down completely.
posted by soundguy99 at 7:20 AM on January 12, 2012 [2 favorites]

Moving into a place with a person you have a crush on is a bad idea if he is interested and a bad idea if he isn't interested.
posted by Adventurer at 10:10 AM on January 12, 2012 [3 favorites]

Um, this may be bad advice. But every time I've had the mind-numbing crush issue ("does he like me? what does this mean? what did his last text mean? can i analyze this differently? should i say something? should i do something") it drives me crazy. Here's what I would do:

1) move out. You have to. Get somewhere cheap for a few months. Sublet. Live on someone's couch.

2) ask him (only him, not your brother too) to grab food some time. Make it a weekend. Do it late-ish. Feel out the vibes during the meal. If they feel good, suggest going to a bar afterwards. Drink an appropriate amount (they do call it liquid courage for a reason) (don't get sloppy though). If he likes you... this is probably the easiest way to find out.
posted by amicamentis at 12:27 PM on January 12, 2012

Thanks guys. I had a feeling that telling him was a bad idea--I just needed an objective perspective to make sure this wasn't another thing where I plan to do something but back out of it for one reason or another (a bad habit of mine). I appreciate your responses!
posted by dean_deen at 1:10 PM on January 12, 2012

I don't think anyone is telling you not to tell him (I think you should!) Just make sure you aren't living with him when you do.
posted by empath at 2:01 PM on January 12, 2012

I don't think anyone is telling you not to tell him (I think you should!) Just make sure you aren't living with him when you do.

I understand that, but the potentially messy implications of telling him even if I found my own place make me give pause. What if we dated while he was still living with my brother and then our relationship ended badly? I would not be able to visit their place without it being awkward, and it would put my bro in a pretty uncomfortable position.

I guess the very ideal-iest situation would be if neither one of us lived in the house. But I don't think he's at a point where he will be moving out sometime in the near future and I myself have been considering moving to another state, just to experience a new place. So more and more this is seeming like something that's not really worth pursuing. The timing and circumstances just aren't there.
posted by dean_deen at 6:35 PM on January 12, 2012

I personally think (and it sounds like you are very healthily leaning this way too) that you might chalk this crush up to overeager, ego-boost-fuelled, late adolescent emotions and therefore not tell him. It sounds like you may first have met this guy and liked him when you were just out of high school, and he was a cool, older guy who was actually paying attention to you. Which is all awesome, it just might not be relationship fodder. It sounds like you have grown up a lot since you've known him, but also that crushing on him has been a confidence building and exciting, romantic pastime for you throughout college, so maybe your new, slightly older, wiser self is being overly influenced by that original, heart-fluttery feeling you may or may not have been nursing this whole time. As someone said above, even though you may feel like you just want to tell him to boost HIS ego, you probably do have some deep-down hopes that your confession might trigger reciprocation. So, I would not tell him. I would make other friends, focus on other things, nurture romantic feelings for other people, maintain your friendship with him as long as it's not just enabling you to keep the crush alive. Maybe you should make a goal of not living with him, because it sounds like he triggers you to flights of romantic fantasy followed by overanalyzing and leading to general making-it-more-real-than-it-is. Get some distance.
posted by dahliachewswell at 12:18 PM on January 13, 2012

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