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

unfaithful boyfriend

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

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. 21
    George King

    Really interesting and honest post! I had those exact feelings of wanting the 97% and was definitely the wrong decision. I think the generational thing is interesting too, you do see a lot of older happier couples of various reasons. It’s not the be all and end all but I think modern society’s culture of instant gratification, social media… a smaller world with travel advances and globalisation… all contribute to people “wanting more” all the time.

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