Friends in forest
Better to drift apart with love—remembering and valuing the great times you had together—than to strangle a friendship by trying to make it work when it doesn’t. (Photo: Boris Jovanovic/Stocksy)
Tough Love

When to Break Up with a Friend

Better to drift apart with love than to strangle a friendship by trying to make it work when it doesn’t

Friends in forest
Boris Jovanovic/Stocksy(Photo)

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Welcome to Tough Love. Every other week, we’re answering your questions about dating, breakups, and everything in between. Our advice giver is Blair Braverman, dogsled racer and author of Welcome to the Goddamn Ice Cube. Have a question of your own? Write to us at

For two years, I had quite possibly the world’s coolest job, running around in the North Woods, teaching middle schoolers all about nature at an environmental learning center. As is natural in any remote little corner of the world, where you have such a distinct, shared experience among a small group of people, I grew really close to my coworkers. Now that many of us have moved on from the center, we’ve started to connect in the real world. My closest friend up north, we’ll call her Dani, was always somebody I found a lot of joy in. She made me laugh a lot after hard days at work, she always had my back, and she was a real comfort to me when I went through a time of great loss. 

We’ve met up a few times in the real world and now I’m having a really difficult time connecting with her. I used to find her funny, but now I find her embarrassing to be around. She has the ability to be really loud and angry. This first brought us together because it manifested itself in the form of loud, angry feminism, which I appreciate. But now I’ve come to learn it can take the form of loud, angry arguments with strangers about things that don’t matter, or loud, angry singing that wakes up sleeping neighbors, or loud, angry flirting with unavailable friends I’ve introduced her to. It gets less and less endearing with time, and as someone who’s naturally pretty shy, it also gets more and more challenging. 

I’m starting to worry that we’re not “real world compatible,” if that’s a thing. Am I a bad person for thinking that? She contacts me frequently to hang out, and I’m finding it hard to say no. How do I balance valuing the love I have/had for her with the direction I’m feeling our friendship evolving?

You used the phrase “real world” three times in this letter, which is interesting, because it suggests that the two whole years you spent at an amazing place—the world’s coolest job—were somehow not real. This might be insider language, the way that you and your coworkers always referred to the outside world from your little nest in the North Woods, but it’s worth stopping for a moment to consider. Those years at your last job were real. They were real life. They were your life. And the friendships you made there were real, too; they don’t stop mattering now that you’ve moved to suburbia (or a small town, or Disneyland, or New York City—whatever the “real world” actually means to you). 

That said, some friendships, even very close ones, are circumstantial. Just because you’re compatible in one situation, especially an isolated and unusual one, doesn’t mean that you’re compatible everywhere. And that’s nobody’s fault. It’s just how things go.

If Dani had one particular behavior that was getting on your nerves (say, her habit of waking up the neighbors) you could talk about it, but it sounds like it’s her personality itself that’s bothering you. She’s loud and bold and passionate, which may have felt great when you were in the North Woods, but it makes you self-conscious in public. It’s not fair to you to regularly go out with someone who makes you want to disappear into a hole. But just as importantly, it’s not fair to Dani. She deserves friends who respect her emotions, who are happy and proud to be out with her. And if you feel embarrassed around her, no matter how well you hide it, she can probably sense that something’s wrong.

That means that if you want to preserve this friendship, you need to find places where you can appreciate Dani’s boldness. Instead of heading to a bar together, suggest camping or canoeing, out in the woods where her antics make you burst out laughing. Hang out at her place (where her neighbors and roommates are, presumably, used to her volume) instead of at yours. Think of the situations where you felt closest at your old job and see if you can replicate them, or some part of them, in this new and different place.

If that’s just not possible, or if you find yourself dreading time together, it’s OK to distance yourself. Better to drift apart with love—remembering and valuing the great times you had together—than to strangle a friendship by trying to make it work when it doesn’t. And anyway, it doesn’t have to be all or nothing: you don’t have to see each other often, but if she really needs you, you can choose to be there for her. Who knows? Your friendship changed once, and it could change again. You might even find yourselves living back in the woods together someday, in yet another stage of your real lives.

Lead Photo: Boris Jovanovic/Stocksy

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