Should I Be Worried If My Boyfriend Cheated on His Ex

When it comes to affairs of the heart, we are all beginners. Some of us, however, at least speak with authority. Introducing Shon Faye, author of The Transgender Issue (2021) and the forthcoming Love in Exile (2025), whose advice caught our eye. Contact her at [email protected] for your own chance at enlightenment. 


Dear Shon,

I’ve been seeing a guy for about a month and it’s been going really well. We get on great, he treats me well, and he’s serious about building something long term. I’m really enjoying getting to know him and was just starting to get excited about the prospect of a relationship with him.

However, recently he confessed that he’d cheated on his ex. He’s been very open about it and his story matches with information that a mutual friend (of his ex’s) has told me.

He said he’s learnt from his mistakes and would never do it again. But the relationship was only two years ago, and they have been in each other’s lives since. They even slept together a few times recently. I believe that it’s over with her, but I don’t know if I should continue seeing him now that I know what he’s done in the past.

I want to believe that people shouldn’t necessarily be judged on past actions, as everyone makes mistakes, and he says the cheating took place after the relationship had pretty much broken down. But the circumstances were premeditated and callous—not a drunken one-night stand, which I feel is more forgivable.

I thought I’d finally found a good guy. He’s really keen to continue seeing me, but understands that I need time to figure things out. Should I see where it goes or cut him off now to protect myself from something that might happen in future?

At a Crossroads


Dear At a Crossroads,

You’re in turmoil because you’re afraid that if you stay with this man, he could repeat his past behavior and hurt you. But if you do not give him the benefit of the doubt, you could be missing out on a shot with a great guy. The first thing I want you to keep in mind is your own worth. This man should have to demonstrate why he is a valuable partner beyond initial chemistry. When considering what to do next, try not to let social pressure that tells you this relationship is a wonderful opportunity slipping through your fingers create a sense of panic.

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