I’m Having An Affair: Really? How’s That Working Out For You?

I'm having an affair

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

I get a lot of emails from readers who write, “I’m having an affair.” They either want to confess because they feel guilty, and/or they want to know if it’s going to work out and if so, how.

I try not to judge people having affairs because every situation is unique. That said, I think more times than not, there are big negatives that go along with having an affair. Not just for the person who is being cheated on, but for the people who are having the affair.

Here’s an email I received from a woman who writes, “I’m having an affair:”


I’m having an affair. It’s been going on for 3.5 years. He finally got a divorce that was just finalized about six weeks ago after a year of separation. Of course I thought things would just fall right into place and we would live happily ever after. Wrong! I’ve never been married before and do not have children. He has a young daughter and has joint custody of her.


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Since the divorce, we have been spending less time together and he seems more distant than ever. But when we do hang out, things are just as great as they ever were and we have the best time together, most recently an out of town trip to see a concert last weekend. He tells me he does not want any obligations, needs some time to focus on taking care of himself and his daughter, and does not want to refer to me as his girlfriend (even though he treats me like one when we are together). 

How can I find the balance of giving him time and space that he needs to heal from the divorce with my need of reassurance that this is actually going somewhere? I absolutely want a future with him, but I don’t want to waste any more time.


Many, many thoughts went through my mind reading this. The first is, when married people have affairs, it isn’t usually because they met someone and fell head-over-heels and just couldn’t resist the person because he/she is their soul mate. When married people have affairs, in my opinion, one of two things is going on:


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1. There is something not working in the marriage.

There is resentment or boredom, or their spouse has some issue that has changed the relationship. Maybe the spouse is sick or is an alcoholic, or is depressed or cheated. Maybe the couple has grown apart-one person is very active and seemingly young and wants to travel, while the other has let him or herself go and is just on a different page.

Maybe the couple never used to argue and now disagree on everything. Maybe there was some tragedy the couple faced and the two people handled it very differently. Maybe there are financial issues. Maybe they parent differently. Maybe one spouse gave all the attention to the children and the other feels ignored/taken for granted.



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Or, maybe the person having the affair has lost interest or respect for the spouse. Maybe one or both feels unappreciated, unloved, no longer cherished. For whatever reason, not being happy in a marriage could cause someone to seek love from someone else (or multiple people.) Those who are happy and committed in a marriage don’t usually have affairs, in my opinion.


2. The person having the affair is unhappy in his or her own life.

He or she might have an addiction or an unresolved issue from the past or from childhood. Maybe the person is unhappy at work or is facing some bad times in another aspect of life—a family member or parent, perhaps. Maybe he/she felt like they couldn’t turn to the spouse for support and can’t communicate so they seek attention/love in someone else’s arms. I’m not saying that cheating is justified, just trying to explain why someone might choose to have an affair.

Maybe the spouse has turned off and is cold and distant and non-communicative. That doesn’t justify having an affair either, but my point is that could be a reason why it happened. On the other hand, maybe the person having the affair never gave the spouse a chance to help him or her. Maybe that person shut him or her out and chose to cheat instead of lean on the spouse.



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So, what I want to say to this reader in regards to “I’m having an affair” is that it doesn’t sound like her boyfriend had the affair because he wanted HER. That’s not to say he doesn’t care for her, but perhaps he got divorced because he was unhappy for other reasons—which have nothing to do with her.

Also, it’s very easy for people cheating to be over-the-top infatuated, giddy all the time and dying to be with the affair every second they can. But then, after they get divorced, the forbidden relationship suddenly seems less hot. Furthermore, the person might be carrying some really bad guilt with them, which makes sex unappealing. Not to mention, this guy might be feeling guilty about what he did to his daughter, and possibly insecure as a parent, so he is trying to spend a ton of time with her.

This man sounds like he is in a lot of pain that could be stemming from years of unhappiness. As I stated above, he might feel very guilty for the affair, he might feel sad for his daughter for the divorce, he might not like himself because he cheated, and now that he is “free” to date his girlfriend—she no longer has to be a secret, he might feel kind of yucky about the whole thing. Also, maybe he doesn’t have respect for the girl because she has been sleeping with a married man for several years. I’m not saying any of these things are true, I’m just speculating.


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Insight into “I’m having an affair:”

When a relationship begins with secrecy and lies and cheating and betrayal (even if the marriage was really bad and the spouse didn’t really care who the other was with), it just has a bad foundation right from the start. I mean where can it really go from here? If they got married, would they look back and say, “Remember when we were first dating? Remember our first kiss? Remember the first time you cried to me? Remember how we couldn’t get enough of each other?”

All these questions would be clouded with unsaid truths involving a wife and daughter who didn’t know where he was, how he came home and had dinner with his family after spending the afternoon with his girlfriend, how he lied to them every time he and his girlfriend had a date. The relationship is tainted. That’s the bottom line.


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I’m not even saying that no relationship can work out if it starts out as an affair. I’m sure many do.  But I know that for myself (and maybe this guy feels the same way) I wouldn’t want that history with someone. I want a beautiful beginning with the person I marry. Maybe that doesn’t matter to some people, but I have to believe that looking in the mirror and facing the truth isn’t rosy with an affair. It’s really something to think about.


What I want to say to this woman is, she might be wise to walk away. If after 3 ½ years this guy won’t call her his girlfriend, how happy in the relationship can she be? She is most likely unhappy most of the time in the relationship, and it probably feels empty, lonely, frustrating and disappointing. These are not things that are desirable in a romantic relationship, are they?

I hope she realizes that she deserves better. She deserves to date a man who respects her, adores her, is proud to walk down the street with her, introduces her to his friends, and loves her like she needs to be loved-not half the time.


As far as the divorced guy, he needs to be in therapy to find out why he cheated and to begin to heal from his divorce. He is correct that he needs to take care of himself and his daughter. But, he also needs to be kind to his girlfriend and think of her, too. It seems he doesn’t want to let her go because he is having fun on his terms, when HE wants it to be fun. He is being selfish in this regard and it makes me kind of mad.


My reader writes “I absolutely want a future with him, but I don’t want to waste any more time.” My advice is: You are wasting your time. Let him go. You deserve better than what he is offering. Let him figure things out. As for you, you have no baggage, other than spending 3 ½ years as a secret, as the other woman. That is not good for self-esteem. YOU DESERVE TO BE HAPPY. I’m sorry to say, but I don’t think this is doing that for you.

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    Jackie Pilossoph

    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: DivorcedGirlSmiling.com

    7 Responses to “I’m Having An Affair: Really? How’s That Working Out For You?”

    1. Angela

      Thank you Jackie. Your post is very insightful and accurate. I went through my separation and divorce three years ago and my husband was having an affair. There were challenges in my marriage and my husband opted not to stay in and fight and decided to move on. And, he did not end up with the woman with whom he had an affair. I hope that the “other woman” will find enough self-love to move on and find a relationship with a man who really does appreciate, love her, and treat her as she deserves to be treated. I imagine it must be awful to be the “other woman”. She deserves more. It must be difficult for her. I always wondered how the “other woman” in my marriage felt through all of this. I will never know. I suspect we have more in common than we ever knew. Good advice.

      • Jackie Pilossoph

        It’s funny because I bet you want to be mad at the other woman, but a part of you has empathy. That said, I constantly fight hard not to judge “the other woman” so much. You just never know what the guy is promising or saying. He could be telling her “My wife and I are separated. She knows I date other women…” and then by the time he tells her the truth, she is already deeply involved. Anyhow, there must be some satisfaction seeing that your ex didn’t end up with the other woman.

    2. K

      Hello Jackie,
      I am recently divorced. I was married for 13 years and caught my husband having an affair with a Co-worker. It was devastating and unexpected. I can honestly say I was shocked along with every single one of our friends and family. Sometimes it’s difficult to hypothesize “why?” While also understanding that there must be a reason. I’ll never know. We have three children and He remains with this other woman.
      I’ve been reading your blog for a while now mostly to hear other’s experience and to try and get some perspective on some very difficult situations. However this one resonated with me. Many times you have addressed the benefits (or lack thereof) of having a amicable relationship with your ex spouse especially when it comes to co-parenting. I agree with this. Unfortunately not many people discuss the courage, selflessness and strength that is needed to continue to have a relationship with someone who has betrayed you it’s one thing when that person was your husband and the father of your children it’s a WHOLE different level of tolerance when the “other woman” is now in the picture.
      There is an expectation when socializing at kids events at soccer games, school events, birthday parties to behave as though nothing happened. To be civil, kind and gracious. This is how it needs to be because the kids do not deserve to witness anything less. With that said, it is extremely difficult for the betrayed former spouse to maintain a constant tolerance. It takes practice, many conversations with supports from friends and a Ton of self reflection to make sure what one is feeling inside does not reflect how one is behaving on the outside. The amount of social emotional strength this requires is unmeasurable. Coupled with the grieving process of a life turned upside down, it can at times feel impossible.
      The reality is I am expected to interact with two people on a regular basis who have caused so much hurt and devastation to both myself and my children (and let me further say no matter how amicable the divorce is—the children are affected). When my children ask questions, I am careful and protect their views of their father. When my children speak about the “other woman” I listen and pass no judgement (on the outside). When my friends state their opinions I listen, keep them to myself and tolerate their choices to either interact with this other woman or not (I learned the hard way on this one).
      When I read your post “having an affair? How’s that working out for you?” , It resonated with me that perhaps the other woman in my case is not as blissfull and content as my ex-spouse portrays them to be. Perhaps this inner turmoil effecting me is also effecting this “other woman”.
      One thing is for sure though, after all is said and done and years pass, time with improve my ability to tolerate them. Like a muscle I’ll have worked at it and practiced and built up a new type of relationship with him and now, the other woman. The kids will respect that when they’re older. I’m not so sure how how time will wear on a relationship whose foundation was built on an affair, lies, deceit and betrayal. So, when you write “how’s that working for you?” …I wonder.

      • Jackie Pilossoph

        I have so much respect for you. Thank you for sharing your unbelievable grace and thoughtfulness on my site. xoxo!!!

    3. Byron

      Great points. I’m the husband who was cheated on. Life was pretty hard until I was able to accept that the affair itself didn’t bring about the demise of our marriage, but another issue did (which I’m now blindingly aware of thanks to a therapist), and that statements she’d made almost nonchalantly were indicators that her happiness was completely dependent on those around her, who she then held accountable – and me in particular. Pretty much a combination of 1 and 2 above.

      Happiness really is an inside job.

      And there I found myself. Middle-aged and joint custody of a young daughter whose world had just been turned upside-down. I’ll get just one chance to be her dad, and I’m going to make the most of it before her teen years take her interests elsewhere. Oh, before the divorce was final I had thoughts of getting back into the dating game – and how much fun that might be. But, once the paperwork was signed, the prize just didn’t seem so shiny anymore? Some day, just not today…

      The fact that you’re single doesn’t mean that you have to be dating someone.

      But, watching her mother, it just reinforces to me why we’re divorced. She really did me a favor by filing. Life is so much more peaceful now. She did me a favor having an affair because I was able to make a clean, justifiable break from her emotionally. We were D-O-N-E. I don’t think I’d ever get involved with someone who cheated on their spouse or significant other – not because I’m afraid they’d do it again, but because I DO now feel that an affair is really just symptomatic of bigger problems – #1 and/or #2. An affair is just a convenient excuse to cover for them. If you’re not happy, say so. Be honest. Own it.

      Winners never cheat, cheaters never win.

    4. Tina

      As I read millions of other people’s stories nothing is like mine. I can’t grasp why. I wonder daily will my husband and the OW actually work out? Here’s mine: him and her coworkers within 4-5 days it showed it’s self. He went missing, being drunk and coming home not touching me. Started 1st time Friday night by Monday 2nd time and even drunker he says “ I love you to death, I’m just not in love with you”. Woke up next morning and never came back. He’s is dating her, relationship or whatever with her. I haven’t talked to him or seen him in 5 weeks. He communicates with our 18 yr old daughter. The OW supposedly posted pic of them. It’s been 5 weeks. Any insight please. I’m drowning


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