Dating a Man Who Has Been Cheated On

I have been dating a guy I met online for about 3 months now. He has been divorced for 16 years. I have never been married. He’s 42, and I am 40. Unfortunately, his ex-wife cheated on him, and married her lover the day after their divorce was final. My boyfriend seems to be VERY obsessed with never allowing anything like that to happen to him again, and is easily upset by any talk of men I dated before him, even though all of those relationships were extremely superficial and I maintain absolutely no contact whatsoever with any man I ever dated before him. My boyfriend has many good qualities, and I really like him a lot (I’m starting to love him). I just wanted to know, in a general way, what does it take for a man to get over being cheated on by an ex-wife, particularly if it has been many years now, and he still seems to be putting up walls? Most of the information I have found on the internet dealing with divorced men pertains to issues surrounding the recently divorced, and most of the information about cheating has to do with divorced men who cheat, not men who were the cheatees rather than the cheaters. Do you have any general advice for a (never married) woman dating a long-divorced man who has trust issues going back 16 years to an unfaithful first wife? I REALLY want my relationship with him to work out. What should I do?

Vicki

If you were ever cheated upon, what would your partner have to do to convince you that he’s safe?

Dear Vicki,

Great question. Straightforward answer. All you have to do is look at it from another angle.

If you were ever cheated upon, what would your partner have to do to convince you that he’s safe?

In a lot of circumstances, there’s not much someone can do explicitly to instill trust. I think back to a girlfriend of mine who had a boyfriend who was polyamorous. This arrangement pretty much meant that he openly cheated on her while she remained faithful to him, hoping that he’d change. She was free to do the same, except she didn’t want to. This experience scarred her and all of her trust issues came to the surface when she started dating a very flirty burgeoning dating coach. She could never believe that a man like me who appreciated other women wouldn’t cheat on her, and she broke up with me (about three times, to be exact.)

I only share that story as an example of how you can have your heart in the right place, but still not do anything to assuage someone with deep-seated issues from their past relationships.

On the other hand, my wife was cheated on by her ex-husband and other long-term ex-boyfriends. How she managed to trust me even when she found a pair of panties in our new hamper after a business trip, is beyond me. But the main reason, I’m guessing, is that I haven’t given her any reasons to doubt my integrity.

And ultimately, Vicki, that’s really all you can do when you’re dating a man who has been cheated on. You can’t erase his past, his hurt, or his shame. All you can do is make him feel safe and loved and lucky.

You can’t erase his past, his hurt, or his shame. All you can do is make him feel safe and loved and lucky.

He may never “get over” the experience of having blind faith in a partner; I know my wife hasn’t. But, if he’s emotionally available — and thereby, a suitable partner — he’ll realize that you have nothing to do with his ex-wife. To keep you at bay because of an awful mistake made by another woman 16 years ago, would effectively mean the end of your relationship. He’s gotta let you in.

The woman who let me in, despite her trust issues, became my wife. The woman who didn’t is just another ex. Which is just a long-winded way of saying: do your best, but it’s not really up to you.