Ask Lynn-Can She Trust Him Again?

She got burned once…but he says he’s changed. Would she be crazy to date him again?

By Lynn Harris

ear Lynn,
I am so confused I don’t know what to do. When I was 18, I started dating a man who was 26. It ended about five months later because he cheated on me all the time. Now four years later, we have started spending time together again. He says when his separation is finalized he wants to try again. I do
There are two schools of thought about cheating and cheaters.
care for him a lot, but I am afraid that I can’t trust him, and that I will just end up hurt again. He has changed in the last four years but I don’t know. I am so confused. Please help.
– Confused

Dear Confused,
There are two schools of thought about cheating and cheaters. One says that a tiger cannot change his stripes—once a cheater, always a cheater. The other, more liberal school suggests that everyone makes mistakes and rehabilitation is certainly possible. I myself know people who have cheated once and never again. It can totally happen.

There are also two separate questions here. One is: Will he cheat again? The other is: Can I trust him, regardless?

As for the first question, we of course cannot know for sure. But let’s look at the evidence we have in your letter. (1) He cheated on you “all the time.” (2) He wants to try again when he finalizes his separation. (3) You are “spending time” together now, before it’s finalized. This fellow sounds to me — far as I can tell, and even if (3) is
I’m not suggesting that you should be a passive, clueless doormat…
utterly innocent — like someone who finds it hard to be without someone (at least one someone). Does it mean he’ll cheat? No. Do I see a red flag or two? Admittedly, yes.

Now for the second question. (And remember, this is a separate question from whether or not he will actually cheat.) Let’s say he is a changed man: Can you find a way to trust him? If you can’t, this relationship, if it starts up again, will be no fun for either of you. Especially you. Can you resist calling to “check up on him” when he’s not around? Can you resist watching him like a hawk to see if he’s eyeballing others when you’re out? I’m not suggesting that you should be a passive, clueless doormat—just wondering if you really do have it in you to give it a chance. In fact, it requires being the opposite of a doormat: believing that you are worthy of not being cheated on. But really, if you feel that you can’t cowgirl up the trust, don’t force it. Sure, there are great stories not only of cheaters reformed, but also of love working out the second time around. But I’ve got to say, my gut is telling me here that there are other fish in the sea—guys whom you won’t have to try to trust. Honestly, if I were you, I’d look for one of them.

Lynn Harris ( is co-creator, with Chris Kalb (, of the award-winning website — you can visit BG's blog to discuss this letter! A longtime journalist, Lynn has written about dating, gender, and culture high and low for Glamour, Marie Claire, The New York Times,,, and many others. She is currently the communications strategist for Breakthrough, a transnational organization that creates pop culture to promote human rights. Submit your own dating questions for Ask Lynn via Your question may be answered in a future column.
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