‘I’m dating my friend’s ex-boyfriend and she’s furious with me’

Dear Roe,

I've started going out with my friend's ex-boyfriend and she's incredibly angry and I don't know what to do. We're all late 20s and have known each other since college. My friend and this man went out for about a year when they were about 19. My friend moved abroad three years ago but we still keep in touch a bit on social media, and we try to meet up when she comes home a couple of times a year.

In college, her ex and I were friendly but never close, but before Covid he moved into the same area as me. Over the summer, we saw each other in our local park and started walking together regularly, then started calling and texting each other a lot, too. Over Christmas we both said we had feelings for each other. Because of Covid, we haven’t got to enjoy the usual dating markers so I think we were both a bit unsure of our official “status” but we’re in a relationship now.

Someone told my friend and she called me, furious, saying I was a bad friend and had betrayed her. She said it was “obvious to everyone” that if you date your friend’s ex that you don’t value that friendship. I feel terrible but also feel like she’s being unfair. Their relationship has been over for years, she is happily with someone else and I feel like a lifetime ban on seeing her ex feels ridiculous. What do I do?

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Firstly, I’d like to apologise to regular readers of this column. We’ve had so many letters from single people asking how to date and meet people during Covid, and never once did I even think to suggest arranging walking dates with your friends’ exes – and apparently it’s a jackpot move! The negligence!

I tease, but genuinely I’m quite heartened and delighted that we’ve had a successful Covid romance story in to the column, so congratulations on finding someone during this difficult time – even if it has come some complications.

I will say upfront that there are some key details missing here, such as whether your friend (for clarity, let’s call her “Anne”) and her ex/your new boyfriend (“Barry”) had a particularly difficult relationship or break-up; whether he treated her badly; and whether she confided in you a lot about their relationship and her heartbreak. These details could explain why Anne feels betrayed.

Some people hold informal social rules about dating friends’ exes for some valuable reasons, including supporting and protecting people who have been treated badly by an ex, and not forcing them to interact frequently in social settings. If a friend confided in you extensively about the relationship, dating their former partner could also feel very uncomfortable and even manipulative because of the intimate knowledge you have about both of them – knowledge that you wouldn’t have, had you not held their trust and confidence.

Anne may also feel betrayed that you didn’t check in with her about how she would feel if you started dating Barry. Because let’s be honest; relationships do not magically appear overnight. You did have months of increasingly sexual tension-filled walks, late-night phone calls and flirty text messages with Barry to realise that you were starting to have feelings for him; to consider how Anne would feel about you and Barry starting to date; and to broach the topic with her before you fully fell head over heels. You chose not to, and to Anne that could feel like you were prioritising the possibility a relationship with Barry over your actual relationship with her.

Anne could also be holding on to the idea that your friendship with her trumps any romantic relationship – but people grow and change over time

However, I am by no means unequivocally on Anne’s side here. If Anne and Barry had a relatively normal relationship and break-up that started when they were teenagers, it does not mean that nearly a decade later, she gets to declare Barry off-limits to any woman she knows. While some of the informal social rules around dating friends’ exes can be valuable, some of them are arbitrary, immature and proprietorial – and assuming that these rules are universal and “obvious to everyone”, as Anne put it, is an unhelpful attitude to hold, and ignores any nuance. And in this case, both time and relationship priorities are very important nuances to consider.

Most people are (hopefully) very different at 19 than how they are at 29, because people grow and evolve and mature – and their relationships do, too. Unless Barry has completely avoided any emotional growth, any life experience, and any other relationships of any kind, you and Anne will be dating very different iterations of the same person. She is feeling possessive over a Barry that existed 10 years ago, and is holding on to a decade-old idea that she and Barry hold a bond that supersedes any bond you could have with him. Now, we can all empathise with certain feelings without enabling them. Anne can understandably feel some complex emotions around her old relationships – but expecting people to end relationships over her feelings isn’t reasonable.

Anne could also be holding on to the idea that your friendship with her trumps any romantic relationship – but again, people grow and change over time, and our priorities change. It is entirely reasonable that after a decade, your priorities have shifted, and that having a committed romantic relationship with someone you really like is more important than a causal friendship with someone you see a couple of times a year.

Our society has some bizarrely conflicting messages that prioritise monogamous relationships above all else, and doesn’t even have scripts for friendship break-ups or acknowledge the grieving process that occurs after a friendship ends – while simultaneously also claiming that you should never choose a partner over your friends. Assumed rules and sweeping generalisations aren’t helpful, and the gap between your perception of this situation and Anne’s perception of it prove that.

Only you know the missing details here, and only you can decide if you’re willing to lose Anne’s friendship for Barry. I think the best bet for keeping both relationships intact is to have a conversation with Anne where you listen to her, acknowledge her feelings, acknowledge the reasons she is upset – and then ask her to listen to and acknowledge your feelings. A point to prioritise is that two people can have different perceptions of a situation and everyone’s feelings can be understandable.

Though you may not be willing to let Anne’s emotions control your romantic relationships, you can still empathise with them. You can also point out that life is very rarely a zero-sum game; you can value the friendship you have with Anne and also value this new romantic relationship.

It is possible that Anne will still feel that she cannot be friends with you if you are dating Barry, and that is her decision to make. But ultimately, like all of us, Anne gets to control her own actions, not yours. Good luck.