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I struggle to make and keep friends. What am I doing wrong?

I have a wonderful husband, happy children, good health and a close relationship with my family. But I’ve always struggled with friendship.

Every time life has changed (new job, change of home) I have a new optimism that this time I’ll get it right. I long for the joys of getting to know people, of laughing and sharing together, or even just casual conversations. But whatever the reasons, something always seems to go wrong and the pattern repeats: I meet people I hope I could be good friends with – fun, kind, interesting, down to earth people – and we get on for a while, but slowly and surely I feel myself being pushed away. Texts and emails go unanswered. Invitations turned down. The spark fizzles and the friendship dies.

I’ve learned to manage my disappointment, but I wish I understood what I do wrong. I do have a really good relationship with my (kind, gentle and intelligent) husband and with my sister, and I have two good female friends I’ve known for many years (although they live some distance away and I don’t think either of them would consider me their best friend). I mention this as I hope it indicates I’m not completely flawed in my approach to other people. But I just can’t get friendship.

This has come to a head because recently I’ve started to get to know some of the parents at my children’s school, who I like, and have taken the first tentative steps towards making friends. But I’m so scared the same pattern will repeat itself and I’ll mess this up again.

Your longer letter gave me some insight as to what might be the problem. You told me about being bullied at school, then sent away to boarding school, where you were very unhappy, the sabotaging of your exams, the self harm, the eating disorder. I think you’ve developed a coping carapace. Your letter started off bright and breezy – but the more you wrote, the more you let the real you out. I wonder if this is how you are in real life? Maybe you attract people who aren’t really right for you. I wonder if you think the “real you” is not someone people would like?

Do you see every new person as a potential friend? This isn’t meant critically, but I think maybe you need to be more discerning, not less. That may seem counterintuitive, but in your letter you came across as someone who is self-aware, kind and has rather a lot going for her. I know it’s easy to define ourselves according to how others see or treat us, but isn’t that giving them too much power?

I wonder how much you test your friendships, and if you do this too soon?

You’ve had a lot to deal with. And yet you have managed to carve out happiness and success. There is a line in your original letter about your parents leaving you on the school steps and driving away leaving you crying. “Why didn’t [they just] turn the car around,” you ask.

You also mentioned that at times you purposely provoke members of your family, forcing them to prove they still love you. And I think this is absolutely key. I wonder how much you test your friendships and whether you do this too soon?

It’s scary to make yourself vulnerable, and if you do this with the wrong people, or too soon in a friendship, and they don’t give you the affirmation you need, it can strengthen your fears. (Some of the examples you gave me of how your “friends” behaved in the past were not friendship, and really rather shoddy behaviour.)

Your child now being at school will have put you back into a place of unhappy memories. So go slowly with these new friends. Be interested in them and responsive, but remember that friendship is not about one person doing all the work, and that almost everyone is insecure about meeting new people. Be kind, but also be kind to yourself; allow yourself the luxury of asking, “Do I really want to be friends with this person?”

Also think back to that little girl crying on the steps, and ask, “What did she need?” Then see if you can provide it for yourself before looking for it in all the potential friends you meet.

• Send your problem to annalisa.barbieri@mac.com. Annalisa regrets she cannot enter into personal correspondence.

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