Does Guy Having An Emotional Affair With His Boss Deserve Another Chance?

having an emotional affair

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

Any kind of cheating is awful. Feeling betrayed is painful, heart wrenching and terribly disappointing. But I personally think it might be harder for a couple to come back from having an emotional affair. Here is one reader’s story:

My husband and I have been together for 13 years and married for a little over a year. months.

Two months ago, he began constantly texting his (female) supervisor. They sent hundreds upon hundreds of texts a week. I began to feel uncomfortable, but he was so reassuring that I let it go. He said he just wanted a friend, and that she was a lesbian so nothing was happening. He plays video games for the majority of his time at home. They began playing together during the day and, at night, he would spend the entire evening after dinner playing games with her.

I decided to check his phone to know if I could truly let it go, but he had deleted all of their texts. When I confronted him about it, he first lied, but then admitted that she had asked him if he found her sexually attractive and he didn’t want that on his phone.

I felt incredibly insecure, as eight years prior he had had an emotional affair with his supervisor at work. I cried, I asked him to stop spending so much time with her so we could nurture our marriage. The hours playing games together continued, usually six if not seven nights a week.

When I begged him to cuddle or go out on a date, he said I was his jailor. He said he would rather be at work than at home. He said he would rather “blow his brains out” than listen to me.

So two weeks ago I filed for divorce. I felt free, since for years he ignored my requests to help with housework or to do things together. He came home the next day and said he blames himself. He says he will move out if that is what I want. He says he ruined our marriage. He cries. He says he will do anything to fix it, and that I am his soulmate.

Then he turns around and says that I never prioritized him over our pets, my parents, my work, my school. He says I never made him feel like he was good enough, and that I don’t accept him as he is.

I am so torn about what to do… I love him. But I also think it takes more than love to make a marriage work. Do I give him yet another chance?

Here’s my advice.

I would never tell a person to leave. I would also never tell a person to stay. That is a personal decision and no one should judge what they decide to do.


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All that said, there are some HUGE issues here with this guy and something needs to change. First of all, this is not his first rodeo. He did the exact same thing eight years ago. An affair with his supervisor. Hmmm…what’s the attraction to cheating on the wife with the boss? This is really upsetting to me and stems from some kind of need/pattern/inner struggle.

Now, let’s take some other facts into this scenario: lying, meanness (“I’d rather blow my brains out than listen to you.” And “You are my jailor.”), video game addiction, not helping out around the house, and basically checking out of the marriage years ago.

I’m not going to tell this woman what to do, but I’m not really understanding her hesitation about leaving such toxicity. What is this guy bringing to the table? Now that she decided she had enough of being treated like crap, the guy is crying and saying he’ll do anything to fix it and that she is his soulmate? Soulmates don’t have affairs with their bosses and ignore their partners for 13 years to play video games. I think this guy is freaking out because he doesn’t want to go through a divorce.

To answer her question, it takes WAY more than love to make a marriage work, but she already knows this. It’s her husband who doesn’t realize it.

The only way this marriage can work is if these two people go to therapy immediately, and if the guy is willing to take accountability for all the things he has done to destroy the marriage. I don’t live with them, so I’m sure the wife isn’t perfect, but who is? But I’m saying, she might have done some things in the marriage that she needs to work on. But that’s OK.

But her husband to me seems like he took the marriage and threw it in the garbage, and that would be something that would be really hard for me to come back from. There might be too much resentment to start fresh.


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If this woman leaves, I think she will be just fine. Doesn’t she deserve to be the love of someone’s life?—someone who knows what marriage, commitment and soulmates really means?

If she decides to give him a third chance, I wouldn’t judge her. Getting divorced and being alone is scary, plus, we don’t know the whole scenario or what their life is like other than what’s in her email. But if she does try to make things work with him, I hope he learns from the past and makes an effort to stop seeking love and attention from his superiors and instead cherish his “soulmate.”

Like this article? Check out, “The Two Biggest Obstacles In Forgiving a Cheater”



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    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

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