How Do You Know That YOU’RE Not Going to Be Unfaithful?

black and white photo of a guy with closed palms

Infidelity might be my favorite subject in the world.

Favorite is probably the wrong term. Fascinating is more like it. I’ve written about infidelity in a bunch of screenplays, touched on it in both of my books, and, needless to say, have considered the impact of cheating as a dating coach.

In fact, it was quite predictable when I realized that all of my favorite authors have dealt with infidelity in both painful and comic fashion: John Updike, John Irving, Philip Roth, Jonathan Franzen.

If I had to explain why, it’s that infidelity cuts to the core of who we are, and who society wants us to be.

We know that we’re supposed to be honest. We know we’re supposed to have integrity. We know what The Ten Commandments say about adultery. We know what our spouses say about it. And yet…

And yet… well, you know “and yet”…

People are people. We mean to do good, but we do bad. We preach one thing but live another.

Studies show that anywhere from 80-95% of Americans feel that extramarital sex is always wrong. Those same studies show that between 20-40% of married individuals have had extramarital sex by the time they reach their sixties.

Such is human nature. We act on emotion, lust, and passion. We kill and lie and screw — all for selfish purposes. And we find a way to justify it or explain it away or deny, deny, deny.

We are a society of hypocrites.

And that brings me to my greatest fear.

I’m not kidding. I’ve never written this down or said it like this before, much less in a public forum.

The scariest thing to me is not that my future wife is going to cheat on me, but rather, that I’m going to cheat on her.

That I’m going be become all the things that I, and the rest of polite society, decries.

A liar.

A hypocrite.

A disappointment.

Now, for the record, I’ve never cheated on anybody.

Unfortunately, for a 35-year-old guy, that’s not quite as sterling a record as it might seem.

I’m a serial dater. I’ve gone out with hundreds of people during my adult life. It was never by design, or for research. It was the process by which I was searching for true love. My parents were married for thirty years and I always wanted to emulate them. If I didn’t feel a relationship had a chance to meet that high standard, I pulled the plug on it quickly.

Which means that my relationships have been measured in terms of months as opposed to years. And staying faithful for five months at a time doesn’t say anything about my ability to resist temptation for five years. Or ten years. Or thirty years.

Which is why I’m afraid….

I’m afraid because my parents told me about their friends who broke up due to infidelity.

I’m afraid because I hear stories of people in their thirties who are already cheating on their wives.

I’m afraid because every one of my girlfriends has had some guy who broke her trust and her heart.

All we have is our word. The word that we give when we say we’re going to call someone. The word we give when we shake hands over a business deal. The word we have with ourselves when our heads hit the pillow at night.

How could I possibly live with myself if I cheated? I couldn’t. I wouldn’t even want to put myself in that position.

And yet…

And yet.

I’m human. I like women. I’m a flirt. I’m a dating coach. I’m always looking for the next best thing — the cheaper flight, the nicer camera, and, of course, that Rhodes Scholar-Supermodel-Top Chef girlfriend who seems to perpetually elude me.

I’m a classic maximizer, as defined by Barry Schwartz in the amazing, paradigm-shifting book, The Paradox of Choice. I could have 93% happiness, but I’ll want 97% happiness. Presuming that 97% even exists.

What maximizers like me rarely consider is the cost of maximizing. The effort to gain a marginal amount is usually far greater than what you gain in “quality” from your endless search. The people who figure this out are the happy ones. The rest of us run around pursuing perfection to our own detriment.

It was a similar concept that spurred me to write the “Hitting On 20” chapter in Why You’re Still Single, and, to this day, it might be the best dating metaphor I’ve ever come up with.

Simply put: Dating is like blackjack. When you get a relationship that is a 20, you stick. If you hit, you’re probably gonna bust.

All I can say is that I hope I have the wisdom to listen to my own advice.

I really don’t wanna mess this up.


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  1. 1

    my favourite quote about infidelity comes from the journalist Tony Parsons-

    “Paul Newman says he wouldn’t go out for a burger when you can have steak at home. But aren’t there times when you just really fancy a burger”

    1. 1.1

      I so do agree with that quote !

  2. 2

    My favorite quote comes from Silent Bob (AKA Kevin Smith):

    There’s a million fine looking women in the world, dude. But, they don’t all bring you lasagna at work. Most of ’em just cheat on you.

  3. 3
    mrs. vee

    Thank you for your extremely brave post, Evan. I think it’s safe to say you speak for all of us in committed relationships.

    Through my own observations, I’ve found that a person’s propensity to cheat is related to his/her ability to be generally satisfied in life. If you agree with that, then it indirectly ties cheating to one’s self-esteem. In fact, if you Google the words “cheating” and “self-esteem” you’ll find roughly 843,000 pages where the two words occur
    in combination.

    From what I can tell, the relationship between cheating and self-esteem
    exists because self-satisfaction depends heavily on trusting
    enough to know and do what’s best for you, forsaking all
    others’ opinions and external pressures. Simply put, if you like
    yourself, then you’ll be confident in your choice in partner, and if
    you’re too busy being deliriously happy with your loved one, then you
    won’t have the time and inclination to look outside the relationship. If,
    on the other hand, you’re more concerned with the relationship’s tangible assets – how much money, attractiveness, social status – a partner can bring to the table in order to make you feel desirable and look good to
    others, then you’ll always be hoping something better will appear around the corner.

    That’s why it’s cliché but true that you must first be happy with yourself before entering into a relationship. Learn to be happy alone, then find someone who fits your mold of happiness. Too often, people work the other
    way, under the belief that a relationship will COMPLETE their happiness, rather than COMPLEMENT it. I know so many lovely individuals who succumb to the powerful illusion that their happiness depends on having a relationship. That’s when the most common mistakes are made, such as
    entering into a relationship with the wrong person and trying to change that person to fit their concept of a happy relationship, or alternatively, trying to change themselves or adjust their expectations for the sake of keeping the relationship afloat.

    All that strife to make it
    work, to shoehorn two people who might be wrong for each other into being together leads to – you guessed it – dissatisfaction… the kind of
    dissatisfaction that could have been avoided if the self-knowledge and
    self-esteem had been there to let go of a partner or pass on him or her person from the outset. And that’s also the type of dissatisfaction that primes a person to seek temporary relief/pleasure/validation in the arms of outside party. In the meantime, fear and insecurity makes one willing to lie to hang onto the current relationship in hand.

    The bottom line to averting an infidelity disaster, I suppose, – and I don’t profess to its foolproof-ness in any way – is to just try to be as happy as possible. We all often forget that we have the power to take
    little steps to make each day better for ourselves. Find out what those things are – whether it’s hugging your cat, watching the History Channel or dancing in your underpants – and focus on those things. Pretty soon
    you’ll find that if you make a habit of having your own contentment as your focus, you’ll be when the right one comes along. And if you take that
    practice with you into your relationship you’ll be ready to cultivate a
    durable relationship, and stronger and better prepared to laugh in the face of temptation when it inevitably strikes.

    All those little things we’ve learned we can do to make ourselves happy become our toolkit to resisting the lure of an enticing extracurricular prospect. You can say to yourself, “why risk wrecking my integrity and losing my fulfilling relationship when I could just as easily go and shoot some hoops/reconfigure the veggie garden/call up my friend and laugh about how much that babe in tight pants turned me on just then?”

    I know it sounds oversimplified, but the mechanism itself is perhaps really as simple as that. It’s happiness that’s never easy. It could take a sizeable part of your life just figuring that bit out. So my recommendation is to throw all your energy into that, and in doing so, you build up your resistance to the temptation of cheating in the process.

    I, too, pray that I’m right. The best of luck to you, Evan.

  4. 4


    Good post and I don’t usually comment but feel compelled here.

    Your parents and their marriage are actually from a different culture but probably a much wiser culture and generation. They don’t have the maximizer mentality (probably in their favor) and so are willing to work harder for something that will work for them.

    Holding out for 97% is a fairy tale akin to Snow White and Sleeping Beauty (or holding out for winning the lottery). Getting 93% and having to do work makes the relationship a keeper to both sides. Anything you have to work for is much more valued.

  5. 5

    How do you know you’re not going to cheat?

    You just don’t.

    It really is that simple. Cheating is a choice some people make, it’s not something that’s forced on them. No matter what excuse or rationalization they want to use to cover up their own personal responsibility.

    All psycho-babble-bullshit aside, if you don’t want to cheat, you just don’t.

    You. Just. Don’t.

  6. 6

    I’ve read books where the author advocates sticking with a relationship if it’s 51% good. To me, that’s settling… putting more faith in scarcity than in abundance. My personal cutoff was 80% good — moving on when I could see early on that criteria was not being met — and I wound up with my own personal version of 93%. Any time I find myself looking askance at the dirty socks on the hall floor I remind myself how grateful I am every time he scoops the cat box without my even asking. Any time I get impatient with his smoking, I remember that, “Hey — he doesn’t nag me about my eating, even though I could stand to lose weight.” I automatically look at the flip side of the annoyance: What does my partner do that’s wonderful? What do I get from my partner I’ve never gotten from anyone else? What do I do that I’m quite sure drives him insane, yet he doesn’t complain about? Do I occasionally look at another guy and think, “Whoa, is he ever hot”? Yep. Do I ever look at Hot Guy and think, “Hey, baby, come to Mama”? Nope. I can appreciate beauty (hotness) in the abstract without having to “own” it. It’s enough for me to look at Brad Pitt without wanting more. Deep contentedness and being happy with what you have — in my case, a marriage that is blissful 93% of the time — is its own reward.

  7. 7
    The Exception

    I tend to believe that people aren’t truly ready for a committed, long term relationship until they have lived a bit and know themselves – like really late 20’s and older. I suppose I feel that one has a better idea of what love is and what will make a marriage work.

    That said, I am not sure that monogamy is truly possible. Yes, there are men and women that do it. I am a monogamous person, but I am also not against the idea of taking “cheating” off the table by simply saying, you tell me about it and I am okay with that.

    The infidelity, in my case, is the lying and loss of trust over anything that is done physically. I can accept curiosity, an interest in someone else, hormonal/biological/chemical response. I can accept that the idea of sleeping with the same person for fifty years can get boring. These are all issues that can be accepted.

    I can not accept dishonesty and lying.

    Why can’t we set realistic expectations for marriage and one another? Is it a realistic expectation to sleep with the same person for decades without venturing out? If you are married in your early twenties? Even if you are married in your thirties your marriage could last 50 years if not longer. Marriages in my family are truly life long experiences.

  8. 8

    Regarding your Rhodes Scholar-Supermodel-Top Chef desire. So if she is 28% Rhodes scholar, 28% Supermodel and 30% Top Chef, it looks like you’re doing really well. Can you expect to get more than 96%. That’s still and A by educational standards!

    Also, is that what most men really want? Or just you? and if so, do you have a brother!? And is he a Rhodes Scholar-Zoolander-Top Chef?Cause I’d love me a guy well dressed man who can sear a foie gras while reciting great Lit or historical facts about the development of the western world an it’s impact…oh who cares. If he’s smart it’s hot! 😛

  9. 9
    Carrie Freeman

    Having sex with the same person for 50 years is only boring if you let it be. Call me crazy here, but there is something completely wonderful and amazing about having a partner who knows how to make you scream, who knows what buttons to push, who knows how to tease and play just the way you like it. Developing a wandering eye, or hand is (in my humble opionion) a sign that you are not trying to re-invest yourself. You have allowed youself to become “bored”, or as I normally put it, you just got LAZY. Relationships, the long ones, the BIG ones, require WORK, every day for the rest of your life. 🙂 You can’t just forget there is someone who loves you, depends on you, needs you and trusts you. Make a choice, don’t let others chose for you. You chose to cheat, then have at it, but please, do it AFTER you let your partner know!! After all, if you can’t stand by your choice, then you are making the wrong choice.

  10. 10
    chris nussbaum

    Our heads are chock full of so much bullshit, its hard to figure out what we as individuals really want sometimes. When you work too much, overboil with stress, strive, strive, strive, and feel overwhelmed in your life, an affair looks and feels like a vacation, a getaway, a place where you need not deal with a daunting and exhausting reality. That’ sthe main attraction — a getaway from reality.

    So – take more true vacations. Set boundaries at work, and commit to more time off. Take your partner with you, and hold onto what’s good and satisfying and relaxing. Shitcan what doesn’t fit in. You won’t need an affair, you’ll feel better, and your partner will draw closer.

    Trust me, it works.

  11. 11

    I am recently seperated from a 9yr marriage. I ended it as I was finding after 9 yrs of being good and saying ” I would leave before I cheated” I found my head turning and often being attracted to other men. I never looked until the last 2 yrs of my marriage, I was married in my mind and heart, then I started to stray, started going out without him alot. And a year ago I met Justin in a town 45 minutes away, my old hometown. I was 34 he was 26, I felt old and unattractive as a married mom of two, so to have someone young and so cute flirt was me was a huge ego boost. I never flirted, but as a married woman I probly shouldnt have gone to an after bar party where I met him to begin with, my 20 yr old niece liked him alot and was very upset her OLD aunt was stealing him. Now I must say I was honest told him I was married but unhappily, he was fresh out of a marriage and she had cheated on him and he was against cheating, I gave him my email and he gave me his number, we spoke a few times and a few emails and my niece caused issues she was so jeolous, we stopped talking because of lies she told us, so did I cheat because we emailed and talked a few times, and I found him to be cute, I never even hugged him? So we stopped speaking and 11 months later I see him at bar in same town we met, I go to that town to get away from hubby, we were on path to divorce for awhile, so I went out to get girl time without him. Again even though marriage is ending I didnt hug Justin, but my thoughts were naughty and he tryed…Will I become a cheater? I have always been very against it, always swore I would end a relationship before I cheated…And I did. Oh and so you know I tryed to leave marriage for past 2 1/2 yrs hubby kept convincing me to stay and financially my job sucked I couldnt leave and finding new job wasnt going anywhere either in small town. But my lovely niece was mad at me and told my husband about Justin even though it was a year ago and nothing happened, and now I have been labeled a cheater, it bugs me, I didnt even hug him. My husband was very jeolous and if I closed my email as he walked in the room I was cheating on him, I closed the screen cause i was talking to a guy, hen really I was done reading my email… I am now seperated and moved to the town I met Justin in, but behaving have not seen him yet, rethinking that one, I am 35 he is now 27, but I think he is too young for me. But I just left husband a week ago and only been in town a week, our paths will cross, we go to the same bar, I am trying to behave and staying home for a few weeks before the newly single girl goes out, give me time to be alone and get head on straight, although I am very happy to be single, ending marriage was mutual, were not fighting, better friends then lovers. Do I have cheater blood in me, because I thought and looked at other men, or is it because after years of boring sex that only lasted 2 minutes and he is only one that enjoys it, did I finally get sick of it and start wanting more? Is it because sometimes you just dont marry mr. right, or does mr. right exist? For some he does, will we ever have what grandma and grandpa had in todays world, with so many divorcing? AM I doomed to be like my family, is it in my blood, sister on hubby 2, mom divorced from number 3, and dad is on wife 5 if you dont count that he married my mom twice thne it would be 6, is that my future…

  12. 12
    Cheating Girlfriend

    Well she did it, she cheated. I still can't believe it.

  13. 13

    Evan, from experience Ive learned that men cheat whether their girlfriend or wife makes them feel good or not. Ive known men who have the nicest girlfriend/wife, the most coolest, the most supportive woman YET they cheat nevertheless. Often times its not about her or how she makes him feel, its how he feels. Men are very selfish beings, all humans are, but men on a much larger scale than women. We can see this in most cultures, society, human history, and even when you examine animals. Most males are prone to think of themselves first, thus as you mention, they are maximizers.  

    From my own experiences, I get hit on by MANY MANY taken men and am absolutely astonish to find that often times these men have very “happy” wives/girlfriend. Men are like babies, they want what they want, often not realizing what they can lose in the process. I can examine this in my nephews, ANYTHING that can excite and make them feel good, they will want it immediately…often times not realizing it comes at a cost. But my nieces even at young ages, as women are, are indefinitely more complex as they process more in their mind before acting.

  14. 14
    Jenny Wren

    My husband has an exhausting job, works long hours and feels angry and resentful about it. Being married is just another boring chore with unwelcome demands. He would really rather be on his own even in a caravan without me or the children. He has just had enough of other people altogether so he refuses all intimacy and says sex has long ago turned into a boring chore which he has refused to even talk about for years. But last September he stopped off in Thailand with the express purpose of using prostitutes and he tells me that he had about 7 or 8 in three days. On his next trip he did the same but met a shop girl who became the object of intense romantic fantasies. He showered her with money, gifts and promises of monthly maintenance. He planned trips to Italy and france, called her his princess and said how hot she was and how he couldn’t wait to be together. He arranged the best five star secluded hotel getaway with private pools for naked bathing. Then her husband found out and she had to call it off. I had already found out and begged him not to fly half way round the world to Thailand to take her on this romantic holiday, but when I begged, it made no difference. It was only her husband finding out that made the plan fall through. Within a week he was abroad again for work, this time another continent, another prostitute, but this one he invited to accompany him on a ten day luxury road trip. A slip of the tongue during a phone conversation with me, when he spoke of ‘we’ checking into a hotel, meant that he thought I’d guessed what he was doing so he confessed it all to me when his trip was finished. What I genuinely don’t understand is why he wants all this, with his lies and the girls’ insincerities, rather than a real connection with a passionate and pretty wife who loves and desires him.

    1. 14.1

      I’d be quite worried about what disease I might catch from him. The marriage sounds finished. Probably time to care for yourself and your children and cut him loose.

  15. 15
    Saint Stephen

    @Jenny Wren-
    Are you still married to this man?
    You must be very brave to stick with this man in the very face of dishonesty, unfaithfulness, lies and insincerity.
    I’m no relationship expert- but in case you harbor the feeling of making your marriage work, you can look around you and try to see what have changed over the years.
    Maybe if you have added some pounds- you can work out a bit and look for ways to “rekindle” your sex life. And the both of you will also need to have a deep seated conversation to see if you can smoothing up the rough edges of your marriage.
    -Good luck which ever way you choose…

  16. 16

    I see this is quite an old post but I wanted to offer this insight to Jenny Wren, perhaps more so for the benefit of anyone in a similar situation that ends up reading this string. My dear… I strongly suspect your husband struggles with depression. My ex husband deals with depression and the situation you have described sounds similar to my own, however more extreme. I did read a lot about depression when trying to decide what I should do and there were many stories written by wives of depressed husbands that sound similar to yours. You may want to read some of those but I recommend brushing past the articles that speak only of your need to give unwavering support to your husband and, instead, opt for those that speak more of how to get yourself and your children through it.

  17. 17

    Evan, coming from someone who was “the other woman” at one point in my life (I got over it, it was brief, it’s ok but a huge eye opener), you should not be married. You should let your wife someone who will be 100% loyal to her, as I explain further below…

    If you have fears/desires to cheat even if you are in a happy marriage, then you shouldn’t have gotten married in the first place. Why not just be a single dad and date multiple women if you love to flirt? You are the classic case of you want your cake and eat it to. I think it’s ok to look at women, but don’t touch or verbally flirt.

    If I had a guy tell me that our relationship was happy, fun and great and that he had his cake and told me he had fears of wanting to eat it to or possibly might act on it, I’d walk away like a self respectable woman. I will not put energy into something like that or feel like I’m in a gray area. That tells me right there that he has no confidence in himself to just 100% commit to me or just have confidence in himself! And telling me that would make me feel sad and fearful like I’m being hung on a string and some kind of back up plan that he could run home to because he feels “safe” and “comfortable?!” People like that don’t change and never will and it’s the sucker women who fall for it, in a sense I feel bad for the married ones.

    I am 37 and currently single and I am a nurturer, one man woman. Never in my life when I have been in a committed relationship I have never felt like touching or flirting with another guy. Once you’re in a commitment, you should make it grow from there.

    1. 17.1
      Evan Marc Katz

      Thanks, KC. My wife and I have now been married for nine years and are happy and monogamous. Feel free to read the rest of my blog or subscribe to my newsletter to learn more about how to make healthy relationship choices.

  18. 18

    That’s great, but are you still flirting with other women? You shouldn’t be doing that if that is the case!

    1. 18.1
      Evan Marc Katz

      My life is very different than 10 years ago. Suburbs, two kids, far fewer instances around anyone but families. But my wife and I still have outgoing, flirtatious personalities that haven’t changed. Being friendly to members of the opposite sex is normal and healthy, presuming an underlying level of trust. We have that in spades.

  19. 19

    👍🏼♠️ Yes I will subscribe to the blog!

  20. 20

    I dated my boyfriend for 26 months. We have been happily together and it was a long distance where we would visit each other every month minimum. We would do some activities together. Now he is leaving the country (Germany) going back to the States for his one year program. The last 4 month I have been very busy But we still saw each other. But I had a weird gut feeling. I still made time to see him and we spend weekends together having fun and doing some trips. This past weekend we spend together again. It is for now the last weekend and he is leaving tomorrow. And somehow I really had a weird gut feeling and I did something I would never do. While he went to the gym I checkt his WhatsApp. And I found out two month ago he met up with an other woman. They had sex. After that night they spend, he did not reply back to her messages at all, where she blasted his phone with messages. I am deeply sad right now and do not know what to do next. It is very disappointing for me to find out something like this happened. Because for me I build on trust. Ever since we met I also never had any urge to check his phone or do something like this. I have never expected him to cheat on me. I did not tell him that I check his phone and found out that he cheated. And I acted absolutely normal. But I really don’t know what that means. Why he cheated on me, and what he acts like normal, and what the problem it. Maybe you can help me to understand, why a men would cheat in this kind of situation and what his thought process is. Thanks

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