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Is it ever acceptable to date a close friend's ex-boyfriend?

The Independent

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October 09, 2025

The Indy's agony aunt Victoria Richards is here to help

- Victoria Richards

Is it ever acceptable to date a close friend's ex-boyfriend?

Dear Vix, A close friend of mine was dating someone for a few months - nothing big, nothing serious – and then he ended it, because he didn’t feel they were compatible, long term. They're very different: she’s an introvert, he’s extroverted. She likes quiet nights in, he likes going out clubbing. I can see how he came to that conclusion.

My friend didn't seem that upset about it - she said, too, that she didn't think they had a future together; that it was just a short-term, fun fling. She's already dating someone else she appears much more comfortable with. She seems happy.

The problem is: the first time I met her ex, I was super attracted to him - and we were so compatible! I couldn't believe she had met someone so suited (to me) and I'll admit I was pretty envious. But, given he was dating my friend, I put him out of my mind... until a few weeks ago.

We ran into each other at an event and the spark was definitely there - nothing happened, but now I feel so guilty. He asked for my number and yes, I confess: I gave it to him. Since then, we've been talking a lot and he's asked if I want to meet up – but I keep hesitating and putting off answering, because I don't know what to do.

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