How can I end a strained friendship as gently as possible? | Ask Annalisa Barbieri

During university, I became close friends with a girl who I had a lot in common with. She is very loyal, a great listener, and used to be a fun companion. She has been supportive of me in tough times.

Yet over time, I realised she has other, difficult qualities: she has no boundaries and asks deeply personal, often invasive questions. She casts frequent judgment on the decisions of others, is conflict-prone and has a hard time apologising afterwards. This comes from the family dynamic she learned growing up.

A number of people have ended friendships with her. Each of these hurt her deeply. At the time, I felt she deserved the chance to grow and change. I suggested therapy could help with her relationship issues, but she stopped going almost immediately.

We’ve reached our 30s, and she may never change. In fact, things have got worse. She’s been fired from multiple jobs, lost most of her friends. She has moved back in with her family and that has exacerbated her unhappiness. The two of us went on a holiday together recently and I was miserable; I pushed back on her constant complaining and cruel comments about others, and we left on a tense note.

I don’t want to invest more time in this friendship, but I want to end it with as much kindness as possible. I recently moved to another country; we talk less and I hardly see her, but she wants to visit next year, and she expects to be invited to my wedding. I don’t want to manage her on my wedding day or risk her starting a conflict. Sadly, I don’t want her there at all.

I could let the friendship fade quietly and not send a wedding invitation, but I don’t like the idea of ghosting her. Or I could wait until she asks to visit, and then have the hard conversation. Another idea is to be proactive and reach out now. What’s the right way to do this? What should I say?

It would be an ideal world, in some ways, if we could be completely honest with people but then we seldom factor in what they might want to say to us.

I went to the conflict resolution expert and psychotherapist Gabrielle Rifkind. We both heard you that you want to end this friendship but we did want to propose some options.

Rifkind said: “Your friend has been a very good friend at the beginning, so does have the capacity to be generous and kind. I know you have invested a huge amount in the friendship and you may be exhausted, but she is only 30; and there is still time to change!

She also pointed out that your friend has very possibly lost her confidence: losing friends and jobs. “When things start to go wrong, we can become very bitter and it’s possible for the worse side of us to emerge.” It’s then we really need our friends to help us find our way back. But I appreciate you’ve really tried and possibly have had enough.

If you let it fizzle this will involve discomfort for you as you dodge her, but does keep the door open. And also she may well lose contact with you.

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If you have a frank conversation with a view to ending it, this would be final, but may not be as clean as you think (and be prepared to hear some things about you from her that may or may not be true but are likely to wind you up). Or, you could have a conversation with her and explore how she sees things and take it from there.

Rifkind suggested that if you do have a conversation, do it well before the wedding. “You could start with something like: We’ve had a very good friendship, but it has become more difficult recently – can we talk about some of these things and how we can improve it?” If therapy comes up again, Rifkind wondered if your friend would try group therapy, where how we interact with others is a factor.

“Maybe going on holiday with her was a very intense thing to do,” said Rifkind, “but there are other things you can do in friendships that aren’t so intense.”

I asked Rifkind at what point do you think “I’ve had enough” and she said: “It depends: if you’ve got a satisfying life and feel well-resourced then maybe you can tolerate a bit of bad behaviour and give her a long rein. Sometimes, we have to find our better selves however annoying people are.” I asked why. “Because sometimes people need that loving support if they are to change and if we live in a world where we have enough loving support ourselves, then maybe we can do that for others.”

Of course, no friendship or relationship should damage you long term. In your shoes I’d get some distance from your holiday and your friend and see how you feel in a bit. No one likes waiting but it’s often the most proactive thing to do.

Gabrielle and Annalisa did a podcast together about managing differences that you may also find useful.

Every week Annalisa Barbieri addresses a personal problem sent in by a reader. If you would like advice from Annalisa, please send your problem to [email protected]. Annalisa regrets she cannot enter into personal correspondence. Submissions are subject to our terms and conditions.