Having An Affair? How’s That Working Out For You?

having an affair

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

Purely based on the title of this blog post, you are probably thinking two things: 1. Jackie got divorced because her husband was having an affair, and 2. Jackie is extremely judgmental when it comes to those having an affair, and has an inability to be open-minded in this regard.


So first of all, NEITHER of these things is true. So why would I choose a title that sounds like I’m bitter or judgmental towards those having an affair?” Because there are some big negatives that go along with having an affair, not for the person who is being cheated on, but for “the other woman” as well.


A good example is this reader, who is the other woman:


We had an affair 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.


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 that is their soul mate. When married people have affairs, in my opinion, one of two things is going on:


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 kids and the other feels ignored/taken for granted. 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 will 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 their 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 taking sides. Maybe the spouse has turned off and is cold and distant and non-communicative. Not that that justifies having an affair, but my point is that it 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.



Katz and Stefani Family Law Attorneys


So, what I want to say to this reader 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 obviously, he got divorced because he was unhappy for other reasons—which have nothing to do with her.


So now, being extremely naïve, this woman thought that she would move right in and they would live happily ever after. What she doesn’t realize is, this man is in a lot of pain, that could be stemming from years of unhappiness. 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. Maybe he doesn’t have respect for the girl because she has been sleeping with a married man for 3 ½ years. I’m not saying any of these things are true, I’m just speculating.


The thing about affairs is, when a relationship begins with secrecy and lies and cheating and betrayal (even if the marriage was really bad and the wife didn’t really care who he 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 first met? 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.




I’m not even saying that no relationship can work out if it starts out as an affair. I’m sure some do. In fact I can think of a few right now. 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 someone 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, (and I feel badly if this post upsets her-I’m just trying to help) is that 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? Not very.


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. 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 for now. 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.

Like this post? Check out, “A Cheating Spouse Doesn’t Automatically Mean Divorce.”




Buy novels by Jackie Pilossoph




Featured Expert Articles

Jackie Pilossoph Jackie Pilossoph
Creator, Editor-in-chief, Divorced Girl Smiling
20 Things I Wish I Could Have Told My Newly Separated Self

20 Things I Wish I Could Have Told My Newly Separated Self

Elaine Koby Mossr Elaine Koby Moss
Vice-president and Senior Advisor, Vestor Capital
Want Financial Security After Divorce? Here’s Your Checklist

Want Financial Security After Divorce? Here’s Your Checklist

Dan Stefani Dan Stefani
Divorce Attorney, Principal, Katz & Stefani
Thinking About Divorce? Here Is Your Legal Consultation

Thinking About Divorce? Here Is Your Legal Consultation

Jeremy Woods Jeremy Woods
Senior Residential Mortgage Banker, CIBC
Your Mortgage And Divorce: 4 Reasons To Refinance ASAP

Your Mortgage And Divorce: 4 Reasons To Refinance ASAP

Leslie Glazier Leslie Glazier
Real Estate Agent, @properties, Certified Real Estate Divorce Specialist
Hiring a real estate agent

11 Questions To Ask When Hiring a Real Estate Agent During Your Divorce

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.

6 Responses to “Having An Affair? 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


Leave a Reply

Your email address will not be published. Required fields are marked *