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Home / Lifestyle

Ask an expert: I’m dating my friend’s ex - is that wrong?

By Lori Gottlieb
New York Times·
16 May, 2025 12:00 AM5 mins to read

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Relationships don’t operate on a clear-cut system of “right” and “wrong.” They operate in the murky waters of feelings. Photo / Marta Monteiro, The New York Times

Relationships don’t operate on a clear-cut system of “right” and “wrong.” They operate in the murky waters of feelings. Photo / Marta Monteiro, The New York Times

Q: I have been friends with two women who have been a couple for nine years. They recently broke up. I remained friends with both of them, trying to support them equally through their breakup. One of them, whom I’ll call “Alice,” wanted me to not be friends with “Jane.” She said she needed a friend who was all hers. I told her I could not do that and wanted to remain friends with both.

After a couple of months, Alice started dating someone else and seemed happy. She told me she was moving on.

About a week after that, Jane and I started having romantic feelings for each other. After we determined this might be a serious relationship, we told Alice. At first, Alice said she was happy for us and that these things happen. But after getting off the call, she texted that she needed space. She will not talk to me now and has told mutual friends untrue things about me. Most of our friends are trying to be friends with both of us, but some are excluding me.

My relationship with Jane is going well. We are not getting any younger and really want our chance at a lasting relationship. But I miss my friend.

Was I wrong to start dating my friend’s ex so soon? How long are people “supposed” to wait?

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From the therapist: The problem here is that relationships (friendships included) don’t operate on a clear-cut system of “right” and “wrong”. They operate in the murky waters of feelings.

Feelings and morality are two different things, and you’ve been considering the situation from what you believe is a morally defensible stance. You supported both friends during their breakup – a tricky and delicate balancing act. When it became clear that a romantic relationship with Jane was brewing, you reflected, talked and disclosed. And from your perspective, Alice had already reached a new chapter in her life – at least externally.

But here’s the hard truth: Alice might have said she was moving on, but feelings don’t always keep pace with our words or intentions. This was a nine-year relationship, and only two months had passed since it ended. Sometimes we think we’re ready to handle something until we’re actually confronted with it. Seeing her ex with someone else – and someone who’s been a longtime close and trusted mutual friend – could understandably cause her pain.

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I think a part of you knew this would be the likely outcome. If Alice felt insecure about your friendship with Jane in the emotionally fragile aftermath of their relationship, she probably would not take well to your dating her.

There’s no universally accepted “waiting period” after a breakup that magically absolves everyone from various people’s expectations. But keep in mind that Alice’s reaction isn’t really about “the rules of dating etiquette” or who’s technically allowed to love whom and when. It’s about grief: the grief of losing a partner, a close friend and a loyal confidante, in the span of months – even if Alice initiated the breakup (you don’t say which way that went), or began seeing someone new, or you believed she should be fine. The fact is, you made a decision to date Jane while your friend Alice was grieving her own relationship with her.

But here’s another truth that exists alongside the first one: You can choose to prioritise your joy.

What you’re experiencing now – loss, confusion, a social ripple effect – is the price of this complexity. You miss Alice because losing a friendship, especially a long-standing one, is deeply impactful. You wish Alice could see your happiness as separate from her pain, and maybe one day she will. But for now, the space she’s asked for might be necessary for both of you to find your own clarity.

You might consider honouring her need for space with a single thoughtful message indicating that even with this space, she matters to you. Something like, “Thinking of you. I’m sorry we’re not in a good place right now,” while also letting her know that you’d welcome a conversation if and when she’s ready. No demands, no justifications, just a reminder, as she probably feels betrayed and abandoned, that you have her in mind and are leaving the door wide open for whatever might happen next, whenever (if ever) next might be.

As for the mutual friends who are excluding you – this happens in breakups of all kinds. Some friends take sides based on loyalty, whom they knew first or whose version of events they heard. Others may simply be uncomfortable with the complications. Focus on nurturing the friendships that remain supportive.

In matters of the heart, we can’t always time our feelings conveniently. What matters most is that we handle them with grace and integrity, and accept the consequences that go with our choices.

This article originally appeared in The New York Times.

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Written by: Lori Gottlieb

Photographs by: Marta Monteiro

©2025 THE NEW YORK TIMES

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