How To Tell Your Guy Friend You Like Him

Dear Heather,

I’ve been friends with this guy for almost five years now, and I’ve had a crush on him for four years. I’ve never told him how I truly feel because I’m so afraid I’ll ruin our friendship. We have both established that he’s like a brother to me and I’m like his little sister, so it feels like he’s off limits. I’m so afraid of losing him, but I know I want to be more than that. He has always been there for me but I also know he’s like that with a lot of girls. He doesn’t mean to flirt, I don’t think he even knows how to flirt, he’s just genuinely nice to everyone. I love that about him. I’m just worried that if I say something it will get awkward, or worse, we’ll go out and I’ll end up hurting the most important guy in my life.

This has been eating me up inside for years because I know I can go to him for anything but this. Now we’re both seniors and most likely going to go to different colleges and I feel like no matter what I do I might regret it. I can either tell him and possibly damage our friendship, or not do anything and regret never telling him. Please help.

michael cera

You’re probably not going to love my answer, but here goes: you have to tell him how you feel. I mean, okay, you don’t have to, but I think you should. You’ve liked this guy for four years. Four years! That’s such a long time. It sounds like you really care about him and really want to be with him, and he also sounds like a pretty great guy from what I can tell. You’re right – if you don’t say anything, you might regret it for a long time. That feeling sucks, and honestly, it’s better to get this off your chest than to wonder about it forever. 

I also want to be totally honest about this, even if it’s going to suck to hear. If you two are seniors and are headed to different colleges in a few months, then this is the perfect time to speak up. Why? Well, if you guys are just friends, chances are pretty good that you’re going to drift apart in college as you both meet new people, make new friends, start new lives, and yes, potentially develop crushes on other people. I’m not saying your friendship will disappear – if it’s very strong, you’ll stay in touch – but you will definitely drift apart a bit. So, if you tell him you like him and he doesn’t feel the same way, things will work themselves out.

The downside to this is that, again, you’re going to different colleges where you’ll both start new lives. If you tell him you like him and he says he likes you back, things will be complicated. Long-distance relationships are tough, especially when you’re both college freshmen. BUT it is not impossible to make things work, and telling him now gives you two months to be together in that way before you have to start school.

All of that aside, you should absolutely tell him, and I would say that even if the college thing wasn’t an issue. You don’t know that he doesn’t feel the same way. You don’t know that it will ruin your friendship. You don’t know if you’ll hurt him in the future. You’ll never be able to predict any of that stuff. Your friendship could get ruined from something else, even if you don’t come clean! The point is not to be cynical, it’s to say that you shouldn’t avoid doing this because it could ruin things, because honestly, it’s just not a good enough reason. Imagine years from now, you find out he liked you too, in what could be a movie plot but really does happen IRL (I swear, I’ve watched it happen). Imagine how you would feel knowing nothing ever happened because neither of you tried? UGH. You don’t want that regret.

So, ready to speak up? Hold on, girl. You should start off slow by testing the waters. Flirt with him a little more than usual, and see how reacts to it. If he’s feeling the vibe, he’ll be into it. If not, he’ll back off. Try getting a little touchy-feely with him to see how he likes it. Spend time with him alone, if you guys don’t already do that. Maybe, if the moment is right, try kissing him. It sounds crazy, but it could be easier to do that before having a conversation about things.

If you don’t want to do that, or you do that and then you feel ready to really make the move, it’s time to be honest. You can tell him in person or through texting or on the phone, whatever you’re more comfortable with. Just be real with him. Say that you have a crush on him and you want to try to be something more, but you don’t want to ruin your friendship. Tell him to be honest with you and then respect what he says. Even if he doesn’t feel the same way, though, I promise you’ll feel better that you said something. Just go for it!

Good luck!

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Posted in: Dating, Love Advice
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  • TheMCMushroom275 YT

    Ok, but what if this guy that I am practically besties with is dating one of my other best friends? Also, they don’t see each other THAT often because they go to different schools, but they feel really strongly about each other? I don’t want to lose either of them as friends and I am moving at the end of the year and he is moving to the same school as my friend. It’s just so painful and confusing, I don’t know what to do.