How To Tell Your Best Friend You’re In Love With Him

Dear Veronica,

No offense, but I never thought I’d have to write to an advice columnists about my problems — I’m the kind of person who’s introspective to a fault and very cautious in my personal/romantic affairs. Now, however, I think that’s working against me. I found your column by (of all things!) googling my problems in search of advice. It was your article on the difference between romance and friendship which lead me to think you might be able to help me (

In your article, you told the girl who wrote to you that she was founding her friendships the wrong way, and preventing men from considering her a romantic option. Like that girl, I’m in a lonely and frustrating spot, and like her, I’m a socially/romantically viable, likeable, attractive woman. However, in my case, I founded this friendship so long ago that sex, and even romance, weren’t part of my vocabulary. I’m in love with my oldest friend. My best friend. And he’s single. We both just graduated college, and he lives across the street from me. I see him every day. The thing is, I can’t just risk this friendship haphazardly, the way you suggest in your column; I need him in my life. This friendship means everything to me. I can’t explain it — I don’t have the words. But I think you know what I mean. The time we spend together is beautiful. The thing is, I’ve spent almost a year doing nothing about it and I don’t know how much longer I can take it. What do I do? I think we’re past the point of flirting and seeing what happens; I think I need to go all-or-nothing. But I just can’t bring myself to do it. I’d appreciate any advice you can give me.


- hate signoffs, sorry

Dear Thanks,

I’m going to be straight with you: I think you’re right that your choices are “all” and “nothing,” and I think you have to choose “all.” Why? Because you’re miserable right now, and you’ll only be more miserable if you keep doing this. And although being miserable over someone you love is beautiful in its own way, misery is misery, and misery sucks. If it doesn’t work out, it may take you years to get over it (and you’ll probably have to move); but that’s going to be the case whether you tell him or not, if you think about it. You might as well get a head start.

Because you’re eventually going to fall in love again. I promise. I know you don’t believe me, but think about it: you’re so young that the fact that you’ve fallen in love once already almost guarantees that you’ll be able to do it again. It’ll probably take a while — there are no shortcuts, unfortunately — but I have no doubt that it’ll happen for you.

The question, then, is how to approach this thing. I agree that flirting isn’t going to do it. However, if you’ve been in love for this long, and he knows you so well, I suspect that he understands your feelings, at least at a subconscious level. What you need to do is “raise the subject” in a nonexplicit way: wear something flattering, something sexy, one night; have drinks another night and talk about the kind of love you believe in and what it would look like. And then, after he’s had a week or two to think about all of that, make a move — physically. He’ll either respond or rebuff you, and you’ll have your answer. If he rejects you, you can talk about what it means later, or you can agree not to talk about it. If he’s been feeling the way you have, he’ll be thrilled. Who knows? He may even make the first move, if you make yourself clear enough. Either way, you’re on the path to happiness.

If he rejects you, I know you’re going to be tempted to pretend it never happened. I think that’s a really bad idea. I know that when you’re in love, it feels like just being around that person is enough; but the thing is, while you’re obsessed with him, you’re not going to be able to fall for anyone else, and you’ll only get more and more miserable. At the end of the long day, you’ll be happier knowing that you did everything you could to find someone who could offer you the love that you needed — even if you fail — than realizing that you never gave yourself the chance.

The wonderful thing about human nature is that it changes. We’re easily influenced, and our memories are terrible. Right now, you probably feel like your love is so central to your identity that you wouldn’t be yourself without it. And you’re probably right. But after a while, your identity will change, and you won’t be yourself — your current self, anyway — any more. And you’ll fall in love with someone who represents everything you now want to be. The most important thing for you right now is to trust in your own ability to change and adapt, to find and create beauty in the future that’s greater than or equal to what you have now. No matter how big the hole he leaves in your heart, I know you’ll find a way to fill it.

Best of luck.


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Veronica Mittnacht is a lifelong New Yorker. She has written for,, Soap Opera Digest, Flavorwire, Boldtype, The New York Egotist, and Human Rights First, and once attend more


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