I Have a Crush on My Friend. How Can I Tell Him?


How do you tell a friend you’ve known for years and never considered as a potential mate that you have changed your mind? Reality is, as I’ve evolved and grown, I realize that he is absolutely amazing.

Thanks, Anna

Dear Anna,

Good for you that you’ve evolved and grown to appreciate a man that you’ve never before considered as a potential mate. The only issue standing between you and eternal happiness is this minor one: does this guy think that YOU are absolutely amazing and a potential mate?

If not, this might be an ill-fated love affair.

The only issue standing between you and eternal happiness is this minor one: does this guy think that YOU are absolutely amazing and a potential mate?

Your email is short on information, so I’m left to extrapolate based on my experience as a dating coach. But one thing I can say definitively is this: if this man once had a crush on you and you turned him down because he wasn’t your type, you have a MUCH better chance of entering into a relationship with him. Men, especially nice guys, often stay “friends” with women in hopes of some miraculous situation like yours, where one day, you wake up and realize that the love of her life is right under your nose. (Don’t hold your breath, nice guys, women still tend to prefer the cocky unavailable types.)

On the other hand, if you’ve never had any indication that your friend has had any romantic interest in you before, what makes you think he might be interested in you? Because you’re interested in him? Sorry, but there’s no correlation. Unless he’s a super shy guy who doesn’t understand what every man has been taught since he’s 10 years old – men ask out women – my reflexive reaction is to wonder why he hasn’t ever made a move on you in all of your years as friends? My guess is not that he “didn’t want to ruin the friendship” but rather that he wasn’t attracted to you in “that way.” So, to me, the future of your crush isn’t really at all dependent on how you tell your friend, Anna. It’s dependent entirely upon whether he’s been holding a torch for you for all these years. If he has been, you’re in luck. If not, prepare to have a very, very awkward conversation with your close friend. Either way, I recommend you do it under the influence of alcohol.

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  1. 21

    I’m in a similar situation to Anne. I’m interested in dating a male friend.   We met in college but were never really close and reconnected a year ago purely as friends.   We’ve known each other for 10 years.   We started hanging out platonically a lot the past year and he used to live two hours away so he would drive from far away to see me.   I thought nothing of it.   Then he moved to my city and we were close to each other now. One night we went out and he made a move on me.   I froze.   And we pretended he didn’t try to kiss me.   This was three months ago.   We kept hanging out then, pretending nothing had happened, me sending mixed signals, both of us casually dating other people.   But I recently broke off casual dating because I realized I had strong feelings for him but now I wonder if it is too late?   I still spend a lot of time with him and I don’t want to emasculate him by not letting him make the first move.   He’s a macho type of guy and I’m trying to apply EMK’s philosophy in his book to embrace being the girl and do nothing, let him come to me.   But I feel like that advice applies more to strangers dating versus friends potentially dating.   We recently got back to a great momentum where it isn’t weird after all the mixed signals, we’re having a good time hanging out and enjoying the present and I feel like I am ready to tell him I wasn’t rejecting him when he initially made a move on me but was just scared and surprised.   So should I make a move (physical or verbal) or will that emasculate him?   And if we do date?   Do the same rules apply?   Should I wait to sleep with him?   Because I feel like we already have been on 100 dates (platonically), so I don’t feel weird about sleeping with him sooner if he were ready to commit etc but I guess that is more of a down-the-road concern?   Now I’m just freaking out on how to exactly let him know I like him but not nudge or nag or pressure him.

  2. 22

    So, it appears as though I have developed romantic feelings for my best guy friend. And guess what?   It’s terrible.  
    The worst part about it is that I’m struggling to “move on” with things because we are in a close social circle.   I can’t ignore him because he’s well, my best friend.   And I can’t just turn off the “I like you” switch because if I could then, I would be the luckiest girl in the world.
    He’s not crazy about me; I know this.   I haven’t told him that I have feelings for him, but I’m pretty sure he knows and he doesn’t want to deal with it.   After reading through this blog, I’ve convinced myself that he cares for me as a friend and he’s lonely and so, I’m the “fill-in” girl for now. In some ways, I feel as though I could say the same for him.   I’m not crazy about him, but I love him, I trust him, he’s entirely entertaining and bright, and I want the best for him.
    We have really solid boundaries, well not so sure about the emotional ones.   We share quite a lot about ourselves with each other.   Physically, he never hugs me though, in fact, he never touches me at all. This is probably a good thing.   I think if he actually touched me, it might actually burn.
    However, on occasion, he has done very date-like things (asks me out to shows/movie, comes over to cook dinner, wants to hang out over the weekend, brings me dessert, emails almost every day) but it’s never “romantic,” and it’s always done in the spirit of “best friends.”   Pseudo girlfriend right here, don’t you think?
    He has dated other women over the course of our friendship.   He used to volunteer information about his dates, but now he will only talk to me about other women when I ask him point blank.   And then, no details, just unenthusiastic answers.   I assume he’s down because things aren’t working out with these women, including me.
    There are a couple of guys who seem interested in me at the moment but I’ve kept them at arms length. However, I’m emotionally exhausted from this current situation and I’m ready to move on.   I’m ready to date.   Deep down, I’m scared of how this will affect our friendlationship, but really, its not making me happy anymore.
    I don’t plan on befriending any more men; they’re too easy to fall for.

  3. 23

    Here’s another approach you might try…. Next time you’re hanging out, you could mention that you have a female friend or, perhaps, co-worker etc. who has told you she has a crush on her male best friend. You might then ask his opinion, as a male, what this girl should do.
    Or you could ask whether he thinks male/female best friends could ever be more than just best friends. All this in a light-hearted, casual manner, of course…..
    His reaction should give you a pretty good idea of what his thoughts on the subject are.
    Good luck, and hope it all works out for you!

  4. 24
    attracted to stoff

    Keep in mind that when your reality is revealed…….Things will never be the same between you and your friend.   So ask yourself do you want to Sabotage the existing friendship? Chances are things won’t work out once you cross that line.   Seriously,   Look Before You Leap!!!!!

  5. 25

    My advice would be to tell him how you feel about him if he feels the same way then great if not the friendship needs to end

  6. 26
    Not Jerry

    Never, never pass up a good thing.   You just must get to the bottom of this.

    What if this is the one?

    I have known people who have been dating around, and ultimately found the love of their life was there all along.   Right there!   Right in front of you.

    Make a move.   You’re an adult. You should be able to grab what you want.

    If it ruins your friendship, that is unavoidable.

    1. 26.1
      Becky Bryson

      Agreed 100%, “Not Jerry”. I’m currently struggling with a similar situation as the OP & have been doing a lot of thinking as of the past couple of mo. A LOT. I mean it’s seriously unavoidable & something I can’t stop thinking about, to the point i’m almost nauseous. I’ll be 47 in Aug, never been married, & have no kids. Both by choice of course. However, the older I get, the more my thinking changes……in every aspect of my life. Anyway, I decided i’d perform a Google search on this topic even though I pretty much already decided what i’m going to, just to see how crazy my thinking really is. Your response was almost an exact match with what I have planned to take place real soon. I figured wth, if things go South & become incredibly awkward, so be it. Move on. At least i’ll have it off my chest & can stop worrying about it. I have to disagree with other responses in regards to ruining a friendship or in my case, a friendship of over 25 yrs. IF this person IS IN FACT A TRUE FRIEND, NOTHING should come between that. A true friend is a true friend, no matter what comes between you & that person. If he runs away, in MY OPINION, he wasn’t really that true of a friend. After all, he’s going to know you are most likely going to be hurt, feel let down, upset, etc. Wouldn’t a true friend want to be supportive of you, & help you get through this? Perhaps my definition of a true friend is old fashioned or not what everyone else’s definition of a true friend is, but it is what it is & this “old lady” is stubborn & set in her ways. lol

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