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My fiance has a history of cheating – can I trust him?

Ask Roe: He says he would never cheat on me because I’m ‘the one’ but I hate cheating and I don’t know what to think

Dear Roe,

I have been with my fiance for a year and a half, and we recently got engaged. We met some of his friends to celebrate, including some of his friends he has known since college. Two of the women got very drunk and asked me if I knew what happened in all my fiance’s past relationships. They told me that he had cheated on all his ex-girlfriends. I asked my fiance and he denied it, but one of the women interrupted and said he was lying, and a huge argument broke out between him and the women. The night ended in chaos and over the next few days (after a lot of backtracking) my fiance eventually told me that he had cheated in past relationships but was still furious at his friends for telling me. He says that he was never really in love with any of his exes and was unfulfilled with them and knew the relationships wouldn’t last.

He admits he shouldn’t have cheated and when I asked how I could trust him not to cheat on me, he said he has never and would never cheat on me because I’m “The One”, which is why he proposed. He understands why I would have questions but has said repeatedly he’s never met anyone like me and has never loved anyone like this, so his other relationships aren’t relevant to us. I don’t know what to think. I hate cheating, but on the other hand he has never given me any reason to doubt him and I feel the same way he does, that I’ve never loved anyone like this.

I haven’t told my friends about what happened because I’m sure they’ll all tell me to leave him, but I also don’t know how fair it is to judge him on past relationships from when he was younger. We feel stuck right now. He’s being wonderful and romantic and telling me he can’t wait to marry me, but I have been putting off lots of our planned engagement celebrations because I don’t know what to do.


You don’t know what to do? You should send those women a thank you card and a nice bottle of Prosecco because they have done you a massive favour.

Let’s start with the disclaimers first, shall we? I think cheating is usually an awful betrayal that is often treated very flippantly for something that can really shatter people emotionally. However, life is also long and complicated and people can cheat for reasons that may not be ethically ideal, but are human and understandable. People can also learn and grow and evolve. Sometimes people can make decisions that hurt their partners and betray their values – and never do it again. So yes, it is possible for people to cheat in past relationships and to become trustworthy partners.

That’s the end of the disclaimer. I warn you, dear letter-writer, you may not like the paragraphs that follow, but I promise you that this is also what I would tell my best friend if they asked me, and this opinion comes entirely from me wishing the absolute best for you. Shall we continue? Deep breath, let’s go.

It is entirely possible for people to cheat in past relationships and to become trustworthy partners – but I do not think your fiance is one of those people. As ever, I am not an omniscient being and can only respond to the information that you have given me, so I may be wrong. But there are red flags wildly flapping around this entire situation, and more seem to be falling out of your fiancé's mouth every time he speaks.

First of all, he never told you about the cheating himself. And yes, people should have some right to privacy around previous relationships if they wish – but someone who cheated for understandable reasons and has reflected upon it, learned from it, grown from it, is far more likely to be open to talking about it than someone who just likes getting away with things. Secondly, he continued denying it when confronted, and tried to deflect by being outraged at two women who were simply telling the truth about a pattern of behaviour they had witnessed. And thirdly, and most importantly, is everything he has said about the cheating since.

If your fiance had shown you a level of self-awareness, self-reflection, empathy for his exes, regret from hurting them and evidence that he has really considered his patterns of behaviour and taken steps to address this, like apologising to his exes and going to therapy – maybe then I’d be more hopeful. But that’s not what he did. Instead, he created a self-serving logic for his cheating where the problem isn’t in his inability to end relationships when he gets bored, or his repeated betrayal of women who trust him, or his desire for validation or attention or whatever was driving his repeated cheating – no.

He is outright telling you that if you ever stop feeling like ‘The One’, he will feel justified in cheating on you

According to your fiance, the problem was that the women he was in committed relationships with weren’t incredible enough, weren’t special enough, weren’t “The One” – and that’s why he cheated.

Here’s the problem with that logic. He is outright telling you that if you ever stop feeling like “The One”, he will feel justified in cheating on you. If you two ever hit a rough patch, or if you’re not being incredible every moment of every day, or if he just simply gets bored with the routine of a long-term relationship, then he will happily find distraction in the next new, shiny, pretty novelty person who walks by – and he will blame you for not holding his attention.

His reasoning is selfish, lacking in empathy and self-awareness, and it is setting him up to cheat again. Because here are two things you need to know.

One: good people don’t only treat partners with respect and honesty if they’re The One. They treat partners with respect and honesty because that’s what people deserve, no matter if you end up at an altar together. And your fiance has repeatedly hurt his partners and has chosen a justification that lets him off the hook.

Two: marriage is long.

And there will be times where it is boring, and hard, and there will be times where one or both of you must actively decide to show up and keep choosing each other even when doing so feels unfulfilling. And in those moments, you have to not just be in love with your partner – you have to be in love with the idea of marriage. You have to be fully committed to the idea of showing up and staying faithful even when it’s hard – and if it gets too hard, leaving respectfully. Your fiancé's belief that you being The One will prevent him cheating is unrealistic, unsustainable and places the onus not on him to be a loving and faithful partner – but puts the onus on you to stop him from finding other women appealing.

This man has had many years to change, a year and a half to be honest with you, and the past six weeks to decide who he wants to be – and at every turn, he has chosen to be someone who lies about, justifies, and excuses his own bad behaviour.

You have to make your own choices now. You have only known his man 18 months. You have learned very important information about him in the past six weeks. Choose to be someone who makes good decisions about who she spends the rest of her life with.