Once a Cheater, Always a Cheater?

Hey Evan! I’m dealing with an issue that I can’t find explicitly addressed on one of your old posts, so I thought I’d write and see if you can help. I am 38, and divorced three years. I am looking for a relationship, but perfectly happy with my life in the meantime.

I’ve been seeing a man (40) over the past month. He is very attentive, a great listener, and has put in all the effort of someone who is boyfriend material. He calls, plans dates in advance, and is genuinely interested in me. His kids are the same age as mine and we have great conversations and a lot in common. I enjoy his company and can see this continuing into a relationship, as he has told me he doesn’t want to date anyone else.

However, the reason he is single is that he cheated on his ex-wife. They have been legally separated for a little over a year, and are working on finalizing their divorce. He told me on our third date, and was very upfront about it. He said that they married young, had grown apart, and their relationship hadn’t met his needs for a long time. He had an affair with a woman that he knew (I don’t know from where) with the intention of continuing to see her.

He told his ex, they went to counseling for one session, and then decided to separate. The woman with whom he had an affair didn’t want to continue seeing him, so he’s been single for the duration of his separation. He doesn’t intend to cheat again, but also doesn’t appear to regret it. He seems surprised that people are bothered by it, like how the “couple” friends he had with his ex no longer want to get together with him. It worries me that he doesn’t regret it or even feel bad (but maybe that’s more about me than it is about him). He also said that he has worked on himself about noticing when he’s not happy, being more honest about his circumstances, and not flirting with women in his life as much (that last part also was a red flag to me).

My question is, how much weight do you give to someone’s past? Should I stop seeing him because of his prior actions? Or do I give him a chance because it’s more important to pay attention to how he is today, with me, than how he treated another person before? I appreciate any insight you have for me.

Ready for Lasting Love?
Ready for Lasting Love?


Well, you have to appreciate his honesty. He’s saved you a lot of pain and heartbreak.

I’ve written about infidelity plenty before, but I never bothered to gather any data on whether “once a cheater, always a cheater” is, for the most part, true.

Turns out, it is.

Those who cheated were three times more likely to cheat again.

Those who cheated were three times more likely to cheat again. Which isn’t terribly surprising. Nor is it surprising that women who’ve been cheated on are twice as likely to get cheated on again (thus making them feel like all men are cheaters. They’re not. Some women are just bad judges of character and are drawn to certain types of men.)

Now, is it POSSIBLE for a man to have cheated and still be worth a chance? Sure.

If he kissed a stranger on a Vegas weekend when he was 23 and he’s 45 now, we can probably write it off as a drunken, youthful aberration.

If he had an affair when he was 30 and felt terrible that he wrecked his marriage, it may be forgiveable.


Hell, even if he cheated because his relationship was miserable and sexless and he saw no way out that wasn’t really painful and expensive, I’d be willing to listen.

But he didn’t. You’re dating a guy who cheated who feels absolutely no remorse.

That’s some sociopathic shit, right there.

As a dating coach for women, I tend to be risk averse.

  • Don’t sleep with guys you barely know.
  • Don’t commit to any man who hasn’t committed to you.
  • Don’t fall in love with men in other states and countries.
  • Don’t stay in a relationship where you don’t feel safe and happy.

I think it would be pretty safe to add:

  • Don’t embark on a relationship with an unrepentant cheater.

Like hiring an embezzler to be your accountant or electing a con artist to be your president, you can’t be too surprised when the shit hits the fan.

I hope you have the strength to walk away now, rather than doubling down on your chemistry and his potential. I GUARANTEE there’s another great guy out there who HASN’T proudly cheated on his wife.