Advice For: “I Got Divorced Because I Cheated. How Do I Tell My New Girlfriend?”

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

Advice for: “I got divorced because I cheated. How do I tell my new girlfriend?”

I have a guy friend who got divorced a few years ago. I have seen him go through immense remorse for having an affair while he was married, and guilt that was so intense that he was unable to think about moving on or dating for years. If I recall correctly, after the cheating, he wanted to work it out and his wife was the one who decided to get divorced. He contacted me recently for some advice and we ended up talking yesterday.

“I met someone,” was how the conversation started.

I love love love when I have these conversations with divorced people who really never expected to find love again. It gives me hope and inspiration that divorce doesn’t mean your love life is over—as we all think while going through it.

“She is just like me. We finish each other’s sentences. We’re both Christians. We share the same values. We’re both nerds,” he went on.


Katz and Stefani


I wanted to cry I was so happy for him (and he is not a nerd, but even if he is, he is a cute nerd!). But, in the true light of divorce guilt—that I think takes years of therapy to get over, he continued with, “I haven’t told her why I got divorced yet, and I’m afraid if I tell her I had an affair, she will break up with me.”

Ugh, talk about the shoe dropping. I can definitely see his point, as it sounds like after years he finally found what could be the right match for him, and losing this girl would be devastating. But, he has to tell her. There is no question about it.

I think it will be OK, and I think hearing his story, she will be understanding. But, it has to be the right presentation.

The best way for me to give my advice on what he could say is to put myself in the place of girlfriend, and what I would hear that would make me stay. So, here goes:

“I have to talk to you about something and this is very difficult for me because I really really like you and I’m scared you are going to be upset by this. We’ve never talked about why I got divorced, and I want to tell you the truth. I had an affair and that is why my wife left me. I am not going to justify it and tell you that I don’t regret it. I absolutely regret what I did and I know it was very very wrong. But, my wife and I had been growing apart for a long time and we had lost our connection. I was very lonely and I happened to meet someone who paid attention to me and showed me the affection I was seeking. I realize now that instead of having the affair, I should have gone to my wife and talked to her. I should have gone to therapy or done anything I could to prevent this from happening. But I didn’t and I can’t take it back now.

During the affair, I felt temporary highs that led to me feeling the worst about myself than I ever have in my life. I hated myself and in a sick way, it fueled the affair. I have since gone to therapy and also turned to God to ask forgiveness. All I can do moving forward is–like any divorced person, learn from the mistakes I made and aim to be a better partner for someone else in the future. Humans are not perfect and God knows that, which is why God forgives. You mean the world to me already, and I hope you can forgive me too, and know that I am a much better, wiser person that I was in the past.”

I’m not saying he should say this exact thing, but as a divorced woman, I would be comforted and understanding of this explanation.

I used to be a lot more judgmental when it came to divorced guys who told me they cheated in marriage. I remember one guy I met, I asked him, “Why did you get divorced?” and he replied, “Well, my wife and I were having problems, we were disconnected and I did some things I probably shouldn’t have done.”




I was very judgmental at the time and was disgusted by his answer. Now, if he’d have given me the answer I just wrote, maybe I would have felt differently.

The thing is, learning from our mistakes and being better people is a gift you get in divorce. It’s the only gift, actually, but it is a very valuable one. Think about it. You get a do-over. If you have the grace and self-awareness to admit you were at fault about some things or all things having to do with your divorce, then there’s no stopping you to change, and be the kind of spouse you want to be in your next serious relationship.



It’s hard not to be skeptical and critical and judgmental when dating after divorce. But try to open your heart and empathize that everyone messes up. Didn’t you? Of course you did. So did I.

The key is, both people have to be willing to own up to their mistakes, and willing to get help either through faith or therapy or an addiction program or something else to make sure they don’t repeat the bad behaviors. That’s when second marriages and serious relationships after divorce really work out, and when divorced men and women find true happiness and love that includes peace and clarity in your past. That’s when you can embrace your bright future.


Buy novels by Jackie Pilossoph


Buy novels by Jackie Pilossoph



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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

One Response to “Advice For: “I Got Divorced Because I Cheated. How Do I Tell My New Girlfriend?””

  1. Sensei

    Coming clean about the mistake (and including evidence of self-awareness and accountability while you do it) is the only way forward if you ever want to have a real relationship with someone new. It may or may not repel the new love interest, but it’d come out at some point eventually anyway. Better he/she hears the news directly from you. And better for you to know up front how much capacity your “new love interest” has for being nonjudgmental.


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