Sometimes, you just have to let a person go. It happens all the time in the corporate world and the metrics are fairly clear: the person didn’t make the sales goals, never showed up on time, stole money.

But it’s much harder to know when to let a friend or lover go. We want to hold on and make it work, against all odds.

When is it time to move on?

  1. You spend a lot of time making excuses for their behavior

Maybe they’re just always like that when they’re drunk. Maybe they’re mean to waiters. If you spend a lot of time explaining that he or she has a good side, too, it’s time to move on.

  1. You can’t get them to see you for who you are now, instead of the tubby/goofy screwup you used to be.

You’ve spent a long time improving yourself, and your new friends know you as a fairly competent person. That’s why it’s so hard when an old friend downplays your every achievement by reminding you that you’re still that same fat, clumsy screwup you always were. There’s having friends who ground you, and having friends who bury you. Move on from the latter.

  1. You know every detail of their dramas but they know nothing of yours.

Every friend goes through hard times and needs support. But when the whole friendship is an endless loop of her troubles and she never asks about your life, there’s an imbalance. When you’re tempted to put the phone down while they ramble on and on about their sad little lives without stopping for breath, it’s time to move on.

  1. You need a drink or a nap to recover from time spent with them.

Some friends are exhausting, and not in a good way. They’re like emotional vampires and you need recuperation after every visit. Let them go.

  1. You hate yourself, just a little, for the person you are with them.

Some friends or lovers are just a whole lot of fun. But maybe they’re catty bitches, inviting you to snark along. Or maybe they’re always filling your glass a little too much. Whatever the reason, you leave them and feel like you’ve failed yourself somehow. Time to move on.

It’s understandable that we feel loyal, or we want to fix someone. But sometimes, you just have to tell a loved one that it’s just not working. And, unless there’s a divorce in the mix, there will be no severance package because, don’t worry, this is no wrongful termination.

Firing a Friend


  1. mitternight

    Thanks, John — it’s the way I always judged my daughter’s boyfriends, by what she was like when she was with them.

  2. I think that women, in particular, have this need to fix. It’s a romantic notion, thinking we can make a person a better person. But in the end, that thinking reeks of hubris. Because by not acknowledging your #5, we’re really looking to feel better ourselves when we are with them.

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