When it’s time to break up with your best friend

Cutting ties is never easy. Whether you've outgrown your bestie or can't figure out how to let a good person go, breaking up is oh-so hard to do.


So I have this friend. I used to call him a “sister,” but now I just want rid of him. 

He has betrayed me by sharing my secrets more than once, and he’s just plain mean. The problem is that our lives are so enmeshed that I feel stuck with this vitality-sucker in my life.

I’d like to say he’s changed, but the fact is that he’s always been this way. I thought it was funny when I was 22, but seven years down the road, I see the world differently. He builds himself up by putting people down, laughing at others’ expense, and being gossipy. 

I’ve matured, at least beyond those petty ways. I’m not saying I’m perfect, but I’d be better without him. How do you break up with a friend?

Dear Over It:

Some friendships just aren’t built to stand the test of time. Depending on how close you are, you might try slowly disengaging. If that won’t work, suck it up and put the genuine truth out there.

A few considerations: Consider your decision, because you probably won’t be able to take it back. Consider his feelings, because this makes you a good person. Consider your words, because he may remember them for the rest of his life.

Here’s some dos (and don’ts):

Do it yourself. Don’t involve third-party mutual friends to do your dirty work. You’re the mature one, remember?

Do it in person. Don’t write it in a text or chat message. This can be copy-pasted and used against you, or against himself long after you’re gone. 

Do be nice. Don’t be just as mean as you perceive him to be. Don’t stoop to his level. He is a fellow human being.

Still reticent? Here are some kick-start phrases: “We don’t have the same perspective anymore.” “I can’t be the friend to you that I used to be.” “I’m glad about the years we had.” “I no longer have the energy.”


I’m dating the sweetest woman. I’ll always care, but I’m just not feeling it any more. I’m at my wits end about how to break up without hurting her.

Dear Done:

Stop thinking about it as a hard thing for you, and think about it as something that’s going to be better for her. Tell her the nice things you told me, then say she deserves someone who’s feeling it as much as she is.

The Q is for entertainment purposes and not professional counseling. Send your burning Qs to [email protected]

Illustration by Brad Gibson

This article originally ran in Q magazine. Read the full issue below, and pick up your copy around town.