Dating, Relationships, & Sex, Theory & Essay

Why Cheaters “Win” At Relationships

“Running a mile in under five minutes and thirty seconds”

This was my response to an interview question about the most difficult thing I’ve done as an adult; a “safe” answer that 1) allowed me to segue into some faux self-depreciating discussion about my star-crossed college basketball career (I started off with “Oh yeah. I played ball in college a long, long, long time ago.” It’s not a game with my faux self-depreciation game.), and 2) was a lie.

Ok, it wasn’t a total lie. The 5:30 mile — a somewhat pointless feat of mental and physical anguish my college coach forced us to complete before we were allowed to practice — still haunts me. While others have nightmares about death or falling or getting chased by groups of especially irascible midgets with full clown costumes, thoughts of track shoes and stopwatches give me cold sweats.

But, while running the mile was definitely daunting, it’s nowhere near as difficult as breaking up with a woman — a completely draconian task I’ve (unfortunately) had to do twice.

What makes breaking up with a woman so hard for a man to do? Well, it’s always difficult to give bad news to a person you care about. More importantly, though, much of a man’s life (and much of a man’s “success” in life) is predicated on convincing women we find attractive to say “Yes.” — “Yes, you can have my number,” “Yes, we can have sex,” “Yes, you’re allowed to cum there” and so on. This ongoing socialization has left most of us somewhat ill-equipped to say “No” to a woman we’re even marginally physically attracted to and completely ill-equipped to deal with the guilt-ridden emotional fallout of telling a woman “You know those things you do — the things I practically begged you to do when you still weren’t sure if you wanted to do them to me? Well, I no longer want to do them with you. Sorry!”

But, when I reflect on each of those failed relationships, I can’t help but come back to this one act, an act that could have saved each and prevented my break-up anguish if I’d been willing to do it.


Yup, you read that correctly. The general sense of relationship melancholy preceding each of the break-ups? Solved if I spiced things up by occasionally stepping out. The feeling of “This isn’t working. Maybe I need to end this and explore other options” the aforementioned relationship melancholy eventually leads to? Not an issue if I decided to explore other options while still attempting to work things out. The inevitable frustration with the idea of monogamy? Cured if I completely eschew the entire notion.

This issue goes well beyond me. Even the oft-cited reluctance of many “good guys” — and “good guys” in this sense are eligible men interested in healthy and monogamous relationships — to commit can partially be traced back to how most good guys feel about cheating. Basically, you can argue that it takes longer for a person invested in monogamy to commit because they understand that commitment to be somewhat final, whereas a person not concerned with monogamy will “commit” at anytime to anyone.

In fact, if I’d been willing to cheat — and assuming I was either clever enough to never get caught or with someone willing to forgive my repeated transgressions —  not only would I have “saved” myself from having to break-up with a woman, I’d probably be married (with children) right now.

I’m assuming these last couple paragraphs — which can be interpreted as pro-cheating — comes as a surprise to those familiar with my work. From “five completely selfish reasons why i’ve never cheated” — an entry listing, well, five completely selfish reasons why I’ve never cheated on a mate — to “35 reasons why he cheated,” I’ve made no secret my absolute abhorrence for cheating.

That feeling hasn’t changed. I still abhor cheating, but I’ve began to wonder if this abhorrence is less due to what I thought was some moral code than just plain ole envy wrapped in a layer of self-righteousness. Maybe I just hate the fact that while I’ve had to deal with relationship acrimony and break-up anguish, cheaters seem to take the “easy” way out.

I mean, if you’re spending countless hours and sleepless nights cramming for a final exam while your roommate has a cheat sheet with all the answers, how soon before you either start hating that roommate or just say “F*ck it” and ask him to make you a copy?

Who knows? But, do you know why I lied when asked to name the most difficult thing I’ve done as an adult? I knew the real answer would lead to a conversation I just wasn’t interested in having, and I wasn’t prepared to share what it would say about me.

Hmm. Kind of reminds me of the reasoning behind the lie we tell ourselves when saying “Cheaters never win.”

—The Champ

Damon Young

Damon Young is the editor-in-chief of VSB. He is also a columnist for and EBONY Magazine. And a founding editor for 1839. And he's working on a book of essays to be published by Ecco (HarperCollins). Damon is busy. He lives in Pittsburgh, and he really likes pancakes. Reach him at Or don't. Whatever.

  • I dunno. I still think it depends: What are we defining as a “win” here?

    Figure it like this: My roommate’s ex-gf cheated on him for three months straight before she was caught. Within a year, she’d been just about ostracized from their entire shared social circle and started dating the kind of guy I can only describe as a Pirate Douche. I see her around some clubs these days, and there’s definitely something … gone from her eyes. I wonder what she’d say if I asked her whether it was worth it – and whether her answer would be honest.

  • I think men have a hard time for a few reasons. Women are generally the ones that decide if the relationship will begin so the end is generally at their discretion.

    Men are generally flexible within the confines of said relationship. It generally takes extreme external stimuli for us to act. So being the initiator is kind of foreign.

    This is just a thought but I don’t think men are sufficiently cruel enough. We are used to being rejected b/c of societal expectations that men make the first move. So gettin shot down becomes something you endure.

    I haven’t witnessed sober men just dismiss an “attractive” woman before. They’ll tap dance around the fact that they aren’t feeling you but they won’t say it.

  • Leila

    “A person invested in monogamy to commit because they understand that commitment to be somewhat final, whereas a person not concerned with monogamy will “commit” at anytime to anyone”

    Co-sign with this. I see it all of the time. I have one guy friend who believes that he’s single until he’s married and doesn’t feel obligated to be faithful in relationships and easily goes from girlfriend to girlfriend…..Monogamy is tough. I wouldn’t cheat, but can see why people do…

  • Mo-VSS

    So I don’t think cheaters stay winning. I guess it depends on what one considers winning. If winning is not being monogamous or leaving a trail of hurt behind, then sure. But if winning is openness and honesty then no, they don’t. I used to cheat and it was not fun when u see the hurt it causes others.

    It seems like cheaters win cuz they “get their cake and eat it to,” but in the long run it doesn’t Pam out that way. Especially not when you actually care about someone. While cheating isn’t the ultimate sin in my book, the effects can be extreme to the injured party.

    o guess if you ate talking about just a relationship thats one thing. bit a marriage…nope, cheating is too much of a risk to take lightly. House, kids…all that can be lost in an instant messing around w/stray kitty. So, again “winning” depends on what one wants out of life and that particular situation. Cheating may be a temporary solution to keep one content but rarely does of end well when folks find out.(and don’t they always find out???)

  • DQ

    Everybody gets their comeuppance one way or another. We may not always be around to see it, but whatever investment you put out there, you eventually get “your return”. So to my mind’s eye Cheaters don’t win, (or lose for that matter).

    In terms of relationships, there’s no easy way to do a hard job; whether it’s staying in the relationship and working it out, or breaking up and writing off your investment. I just believe it’s hard for dudes to break it off because if honor and character means something to you, then keeping a commitment means something as well. It’s a type of promise. And coming to the realization that you cannot keep the promise and the result will be that you hurt the one you were supposed to “protect” – that will eff with you.

    Conversely if you never had any intention of being true to your word, than breaking your word is a matter of time and convenience not conscience.

  • Tes

    I think we like to think that cheaters never win because it makes us feel vindicated and elitist that we have never done anything like that, and those who do are just losers. In actuality, cheaters bi-win, especially if they’re with a spouse who just keeps taking them back. They get the new car smell and the comfort of the old jalopy.

    Personally, I don’t think I could ever cheat on a person because I know what kind of effects that can leave behind. I have a homeboy right this minute, terrified of fully commiting to women and breaking many hearts in the process because a girl he was in love with cheated on him once (with multiple dudes, in multiple openings but that’s neither here nor there).

    I think cheating is a cop-out; the person is wanting the other person to find out and end it so they don’t have to. Sure, they come off lookin an @ss, but atleast the person was “less hurt” by what happened. I’d rather you break up with me than give me syphilis any. f*cking. day. Some gifts can’t be returned. Word life.

  • WorthwhileDude

    If you aren’t willing to end a bad relationship, cheating will definately help. Just make sure you get caught. Then she’ll be the one doing the breaking up and you don’t have to worry about letting her down easy. That, or she’ll take you back and you’ve dealt with the relationship melancholy and can come back home to her with a refreshed memory of why you don’t wanna be with someone else. Just don’t count on her actually taking you back, that’s just a bad gamble.

    I’ve had the good fortune to never have to break up with someone where the desire to end it wasn’t mutual. So take my advice with a grain of salt, it is wholly untested and not FDA approved. I am not liable to any adverse side affects up to and including death by psycho woman who won’t settle for slashing tires.

  • Bri

    Why does it have to be all or nothing? There are such things as committed relationships that do not involve monogamy.

  • “In fact, if I’d been willing to cheat — and assuming I was either clever enough to never get caught or with someone willing to forgive my repeated transgressions – not only would I have “saved” myself from having to break-up with a woman, I’d probably be married (with children) right now.”

    ^Or you might have cheated with someone that’ll have you coming home to your pet rabbit boiling in a pot. Cheaters don’t win for the reasons you stated before in your other post. For the selfishness of the moment, cheating can have a person catching disease, their car and personal property destroyed, their relationships destroyed, or hurt through violence etc. Folks never know the extent of crazy and disrupt they are letting into their lives by being dishonest and taking part in a betrayal on that level. Ask Joey Buttafuocos’ wife about Amy Fisher shooting her in the head? Tiger sure wishes one mistress didn’t go to Gloria Allred and he had to pay he!!a to keep her quiet. That’s not even including his children possibly being raised in Sweden and the major millions that went to Elin. Steve McNair has unfortunately not lived to tell the tale. I don’t mean that to be flippant or insensitive, just honest in how it can all come crashing down. Those are lives and families effected and destroyed. By not thinking things through, you can start a chain of events that can cause a lot of pain and irreparable damage. Champ, I know you are against cheating, but I’m making that point in response to this post or idea that “cheaters win”.

    In terms of breaking up: Champ, I know you were speaking from the male point of view (which I respect) and wasn’t trying to act like break ups for women are easy…But just to confirm, it is painful for us too. A break-up can be painful for all involved even if that person needed to be out of your life. In some cases, some women mourn for what could have been, not what was (I can admit I have). In others, they love things about that person and not having that person around, whether they need to be or not, is hurtful. In other situations no one did anything wrong, but the feelings are no longer there. The idea of hurting or rejecting a good person is a horrible dilemma and some people stick it out hoping and praying that God can make them like a person because they are good. People labor with it and don’t want to hurt anyone. It sucks for all of us (again, I know your weren’t saying the contrary).

  • This is interesting. I’ve heard a number of times from guys that the bad feeling from cheating on your spouse and forcing them to break up with you is far easier than the bad feeling you get from having to make the choice yourself. It’s just… interesting… considering we’re the ones who can’t generally make a decision. ;)

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