Ask Polly: Should I Dump My Oldest Friend?

Photo: Mogens Trolle/Getty Images

Dear Polly,

I am friends with a woman I met at my first job out of college. I think our 25-year-plus friendship is beyond repair, and I don’t know how to process and make sense of it.

We were young singles together, commiserating about dating. Then we were both in serious relationships. Then we were both married with young children. But along the way in raising our kids, we each took a different turn. Now with teenagers, our very different ways of approaching life are magnified. She is hyperfocused on her kids, obsessing about the minutia of life, whether her kids or sister or mom, overseeing and managing her kids’ homework and activities. I’m a little more laid-back and no longer want to dissect every nuance and word of every conversation and interaction with others for hours at a time. That was fun in our 20s when we were both trying to figure out men. Now, my mind wanders and I start playing online games when we’re into the second hour of discussing her fight with her sister. I’ve tried to be patient.

We have had two really horrible conversations that started with me trying to offer a different perspective (no, she is not being “screwed” when her 15-year-old forgets to do homework) that quickly disintegrated into accusations and yelling from both of us. I’m not proud of the way I behaved. I tried to tell her that. She thinks I’m no longer supportive of her as a friend and it feels like she is putting the responsibly on me to make it right. I don’t how to do that or whether I should, especially if it means more of the same.

At the same time, I feel so sad and don’t want to lose someone who has been in my life for so long. Any thoughts?

Old Friend

Dear Old Friend,

Some people spend their whole lives playing the victim without noticing how they contribute to the complex situations they find themselves in. “Why is he doing this to me?” they ask when their kid forgets to do his homework. “Why is my sister so unfair? Why is my mother against me? What have I ever done wrong? Why do I keep getting hurt, when all I do is try to help?” Somehow they can only recognize their own good intentions, and they misinterpret everyone else as ill-intentioned or full of malice. They can’t see their own carelessness, but encounter everyone else as careless. Instead of slowing down and trying to understand other people’s motivations or emotions, they use their energy and brain power to evaluate everyone else’s shortcomings and failings. They marvel over each person’s missteps and build elaborate arguments against repeat offenders. If you hint that their perspective is a little one-sided, they regard you as a traitor.

It’s not the deconstruction and the analysis itself that’s the problem, necessarily. Old friends should be able to call each other and be supportive, even when it all amounts to petty griping. If you can’t call your old friend and gripe about your mom or your sister or your spouse, who can you call? Look, there are times when it feels good to be a total bitch about everything. There are times when you don’t want to take anyone else’s side, you just want to rip them to tiny little shreds with someone who knows you well and knows that you’re not ACTUALLY a complete asshole, you’re just going through a tough spot or you’re dealing with an extremely difficult person or you’re just in a terrible mood and fucking shit up feels faintly sporting at the moment.

The problem is, if a friend turns to you for this kind of talk and, over the years, you watch as most of their other relationships fall to pieces and you’re the one remaining friend who’s willing to listen, not only do you become the one person that friend calls over and over again for marathon griping sessions, but you find yourself in the tough position of not being able to support what that friend says about the world. Your old friend talks about her teenager like he’s fucking with her on purpose, and you grow silent. What can you possibly say to that, outside of “No, he’s not doing that TO YOU, and as long as you believe that, you’re going to have a terrible relationship with him”?

People like your friend are seriously fun to know when you’re both younger and you’re engaged in the same acts of mind warfare and repetitive slicing and dicing. But there’s a point where a friend’s inability to grow up, take in new information, and evolve becomes a problem for those who have managed to do so. Because most of us reach a crucial point in our lives when we look around and instead of seeing a bunch of people who are WRONG ABOUT EVERYTHING, we see missed connections, misunderstandings, self-protective measures, personality quirks, defensiveness, and differing priorities. We might want to paint a harsh picture of certain people here and there, thanks to hormonal flux and low blood sugar and weak moments when we just want to join the goddamn zombie army instead of rising above it. But we know and accept that everybody alive is a mess of contradictions. And life is about giving other people a little room to be contradictory, and also giving ourselves room to be a little self-righteous and also a little unfair, a little openhearted and a little judge-y. It’s okay. We’re all the same THAT way. We’re all compromising too much and judging too much and getting hurt and hurting.

Should you dump your old friend because she hasn’t grown the fuck up and figured out how to stop blaming other people for everything that happens to her? Maybe. But you could also simply be at a crossroads where you learn to say no to her, learn to get off the phone with her more quickly, and learn to accept her, flaws and all. This may simply be the moment when you commit to a friendship that has a lot of emotional and historical weight in your life, and you also commit to drawing firm boundaries.

In order to maintain an old friendship, you must make space for each other’s conflicted, contradictory selves. That’s why old friendships matter so much.

So even though it’s easy to say, “MY FRIEND NEVER GREW UP. SHE’S STUCK. SHE CAN’T TELL THE DIFFERENCE BETWEEN A MISTAKE AND A PERSONAL ATTACK,” those are just the shortcomings that you can see clearly because you’re stronger than her in those areas. Your friend sounds like someone who has a habit of intellectualizing her emotions, along with some self-esteem issues and a strong fear of intimacy and vulnerability. She doesn’t have enough to do with herself, so she obsesses about her kids, her mom, and her sister, instead of building something bigger or giving generously of herself in other worthwhile ways.

You should try to empathize with her, first and foremost. But you should also recognize that she sees how YOU hold yourself back and flail and fumble, too. She sees those things just as clearly as you see her flaws. Even if anyone off the street might look at the two of you and say, “Okay, your old friend is nuts and you’re pretty healthy,” that doesn’t matter. What matters is that you’re open enough and generous enough to make room for someone who has become very different from you. You can make space for her flaws. You can give her the gift of your compassion. You can imagine how terrible it must feel to play the victim repeatedly. You can gently nudge her toward a new way of being without yelling and shouting and getting defensive.

Your recent shouting outburst arises from your habit of giving much more than you want to give. So stop doing that. Cut the conversation short when you know it’s going to spiral off to infinity and beyond. I have trouble getting off the phone, too, but it’s not really MORE generous to stay on the phone rolling your eyes for two hours straight. You don’t want to live that way. You can talk for a while and then get off the phone. You can text and say that you can’t talk. It’s uncomfortable at first, but the new world order will be accepted eventually.

Recently, I also accepted that it’s not my job to help one of my old friends with her issues. I can nudge her gently as long as I’m not feeling defensive or angry or put-upon. But overall, my role is to support her and enjoy her great sense of humor and take the good with the bad. I have to maintain certain boundaries. Even though it’s sometimes tempting, when things are great with us, to think, “She’s my best friend! We’re like sisters! We should go on long vacations together and tell each other everything!” those kinds of idealistic leaps of imagination aren’t good for me or for us. I have to keep my expectations in check. When I expect too much, our relationship gets volatile. I feel hurt and disappointed in her. She steps on my toes. I have to keep our differences and limitations in mind at all times if I want to stay friends with her.

There are people you can really lean on and people you have to be careful with. Part of being an adult is recognizing the difference between the two. Sure, you can just cut out the difficult people and only keep a few truly steady, dependable people around you. Plenty of people do that. But I believe in old friends — even old, difficult, flinty friends. I like wild, creative people and hotheads. I don’t want to live without them. And I think there’s something to be said for two people who can give each other space, in spite of great flaws. We are meant to make space for each other, in spite of great flaws, because we are all greatly flawed. Your old friend, in her rambling dissections, may be fumbling for some truth. She may be trying to get what she needs from you, in order to face another day in spite of her pain, in spite of her loneliness, in spite of the countless obstacles in her path. 

Don’t give so much that you’re drained, but take some pride in this old friendship, and take pride in being able to give generously, even when she pisses you off. It feels good to love someone in spite of their flaws. It will teach you to love yourself, in spite of YOUR flaws. Nothing is more soothing than realizing that you have a purpose on the face of this planet, even if it’s only to give other people space to be who they are, in the most mundane of ways.

Old friendships show us how to accept others and accept ourselves. Old friendships show us how to give more than we take. Old friendships teach us to draw healthy boundaries. Your old friend wants you to do more of the work to mend things because she knows she’s not strong enough or vulnerable enough or brave enough to do it. She knows that you ARE strong enough and generous enough to make up for her weaknesses. Even though she probably blames you out of defensiveness, just as she blames most people in her life, she also looks up to you. You don’t have to hear her say that to know it. Take pride that you can be that person for someone else. It’s okay to feel proud of your generous heart. What else is there, on the face of this earth, to feel more proud of than that?


Got a question for Polly? Email Her advice column will appear here every Wednesday.

All letters to become the property of Ask Polly and New York Media LLC and will be edited for length, clarity, and grammatical correctness.

(Click here to subscribe to the Ask Polly RSS feed.)

Order the new Ask Polly book, How To Be A Person in the World, here. Got a question for Polly? Email Her advice column will appear here every Wednesday.

Get Ask Polly delivered weekly.

By submitting your email, you agree to our Terms and Privacy Policy.
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

All letters to become the property of Ask Polly and New York Media LLC and will be edited for length, clarity, and grammatical correctness.

Ask Polly: Should I Dump My Oldest Friend?