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‘I Love My Boyfriend, But I Can’t Stop Cheating!’

Photo-Illustration: Stevie Remsberg

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Dear Polly,

I started cheating on my boyfriends in college, and it’s a habit that has followed me into adulthood. It started out with onetime hookups and escalated into full-on affairs. I always had the comfort of a loving boyfriend while the “other man” could nourish unfed parts of me — my interest in art, my inner social butterfly, my sense of adventure. It’s weird, I remember fantasizing about infidelity when I was younger but have also always craved monogamy.

I find ways to rationalize this extremely selfish behavior (“What they don’t know won’t hurt them”). I’ve even called it a “feminist act.” In other words, I’m delusional.

I’m currently in one of these situations, but it feels harder than before. My current boyfriend and I get along so well. We have so much fun together, laugh at the same things, and he really loves and cares about me. We’re on the same page about almost everything, but I’ve noticed some parts of him that I don’t love. He’s often negative, sometimes short-tempered, pretty unmotivated, and a bit anti-social. I suppose these are the things that have led me to cheating on him, even though I love him.

The guy I’m cheating on him with is also a great guy, but I don’t feel the same comfort, ease, and love with him as I do with my boyfriend. He checks a lot of my boxes (passionate, social, friendly), but I would hate to leave my loving, supportive, compatible boyfriend for someone who might not be worth it. I don’t know what to do. On the one hand, I love my boyfriend. But on the other, I’m literally cheating on him.

Who do I choose? The answer everyone has been giving is “choose yourself,” but I don’t want to give up both of these great men.

Selfish Romantic

Dear Selfish Romantic,

Romance that’s based in selfishness isn’t actually romantic. Romance is all about finding someone and showing them your whole self, and seeing their whole, sometimes unvarnished self, too. Or maybe it’s about wearing a costume and pretending you’re the Marquis de Sade, or driving to three flea markets in a single weekend looking for Wakefield furniture, or sampling the finest kombuchas of the universe while chitchatting about the changing of the guard over at The Paris Review, or eating Cheetos and watching SpongeBob SquarePants. Or in my case, romance is about slogging out to Universal Studios first thing in the morning determined to navigate a crowded, obnoxious, overpriced consumer maze for the sake of my two kids without murdering my spouse in the process.

Maybe you have to pretend or act cheerful or suspend your disbelief a little bit, but with romance, there’s a contract. Romance means you share at least a loose understanding of what you’re doing together. Romance cannot exist when one person is lying. The lies nullify the romance. The lies mean that your partner is trying to live in reality, but you’re bamboozling him for the sake of living in a fantasy world. Your fantasy depends on a heist.

That doesn’t mean that couples must tell each other the full, complete truth about their cheating activities after the fact. Coming clean is not always the most generous and kind act that a person can engage in. But those rare and particular situations are nothing like your situation. In your situation, lying is a crime against the two men you’re milking for affection and support.

Milking is a good word for it. They’re trapped by your lies while you suck the life force out of them. It’s not romantic and it’s not sexy and it’s not just selfish, it’s deeply unethical and punishing and unfair and wildly abusive.

Even if your current excuse is that you’re simply trying to choose between two men, true romance is not about selecting the absolute perfect person and then spending perfect times with that person forever and ever. Romance is not about optimization and eventual elimination of all flaws. Falling in love is not just like engineering a robot dog that will never fall down. Your motherfucking robot dog is going to fall down, over and over again. It will also shit on the floor and whine and chew up your favorite shoes. That’s because your robot dog is not a robot at all. You will come home one night and find your house destroyed and you’ll realize that your robot dog is actually a living, breathing organism with desires and needs of its own. Caring so much about the needs of another living organism that you’re willing to be inconvenienced, taxed, bored, dragged across hot coals every now and then, and even grossed out a little bit: THAT IS THE PEAK APEX MAXIMAL ORGASM OF REAL-LIFE ROMANCE.

Most people need to figure this out the hard way, the same way they eventually figure out that having a great career is not about rapidly climbing to glory and then making big piles of cash. Great careers are built on hard, slow, taxing, satisfying, sometimes frustrating WORK. Great careers are sometimes about tedium and rage and competitive anxiety, and then you have to work very hard to reset, to savor the unexpected folds of the day, to relish a few hours of focused concentration.

If you don’t appreciate or savor your work — when it’s easy AND when it’s a challenge — it is exceedingly difficult to succeed. Likewise, if you refuse to accept your partner’s various flaws, and you lie to your partner about what you’re doing together and who else you’re doing the same stuff with, it is downright impossible to emerge with a life-changing love or to call anything that happens between you romantic. You can call it a successful simulation of “romance.” You can call it a virtual approximation of something like love. But it’s not real.

You may have started down the path to becoming a serial cheater simply because you were sloppy with other people or never took other people’s feelings seriously or you had some sensitivity chip missing (as Jennifer Aniston once memorably described Brad Pitt after he left her for a virtual approximation of a dangerous babe with a heart of gold designed to save humanity from itself). But now your rationalizations are even more blatantly selfish than they were before: “I’m just shopping for the right choice!” you tell yourself, as if your goal is true love and not a kind of hedge meant to deliver more affection and support and enthusiasm than a single, flawed human could ever deliver. You are milking two trapped animals at once. And when the shit hits the fan, you’re going to feel like you’re flaying them alive. It’s not going to feel good.

You already realize that, at some level. Your cells are absorbing the unethical nature of your current experiment. That’s what I think you don’t see. You think you deserve the luxury of dating two men, at some level. You think that you haven’t gotten enough and you, personally, deserve a little more. You’re in more pain and need more than other people. Or you’re less decisive and that’s just how you are! You like cheating! Whatever, that’s you! You’ve always been this way! It’s kind of messed up, sure, but you identify deeply with your dark center. You’re a little bit of a criminal, one who has become attached to the criminal lifestyle. You think it makes you a badass. Even when you say, “I know it’s delusional,” it almost sounds like you’re bragging a tiny bit.

Trust me, you don’t know how delusional it is.

The delusional part goes well beyond the unethical nature of your activities, because the damage to your self-esteem, your daily lived experience, and your worldview at large is so enormous that it’s impossible to map. “He’s often negative, sometimes short-tempered, pretty unmotivated, and a bit anti-social. I suppose these are the things that have led me to cheating on him,” you write. This lies at the heart of your wrongheadedness: to believe that your boyfriend’s flaws are the cause of your cheating is to believe that your own flaws make you worthy of being cheated on, abused, abandoned, you name it. You believe that flaws are moral failures.

It makes sense, then, that you need two men in your life, reassuring you and giving you affection and having sex with you. It’s not just about “one is a negative shut-in, the other socializes!” It’s about trying to distract and soothe yourself in the face of your enormous flaws, which are absolutely unforgivable. This is also where too much moralizing in our discussion has to yield to forgiveness, if you’re going to find a way out of this mess. Because you ALREADY believe that you’re a moral failure. The irony is that to you, flaws are moral failures, but ACTUAL MORAL FAILURES, LIKE CHEATING, ARE MERELY TEENSY LITTLE FLAWS.

The confusion and bewilderment inherent to your current unethical, upside-down world is impossible to overstate. It’s like going to church and believing that it’s a rave, or going to a rave and believing that you’re at an orgy, or going to a hamburger stand and believing that you’re about to meet Jesus. You are reading your astrology forecast stranded on an island. You are sipping a fine cocktail out of a muddy Dixie cup. You are sleeping soundly in a spider’s web. Nothing feels real to you for a reason. You are never satisfied for a reason. You are floating in an aquarium filled with shame for a reason.

There isn’t a good way to sell anyone on ethics these days, particularly since so many of the people who bray the loudest about ethics at this moment in history are among the most depraved cretins in the known universe — and many of them are armed to the teeth, to boot. You aren’t likely to understand at first. I just need for you to INTEND to understand that you’re hurting yourself every single minute you continue to live the way you’re living. Your fantasy world is making you sick in a myriad of ways that aren’t that obvious yet, but they can only get worse. You’re permanently fucking with your balance and your senses. You’re choosing confusion over clarity. You don’t like to reflect on anything because it means letting in all of your self-hatred. This also means you have no room for anyone else. You don’t listen. People are disposable, even when you crave a permanent relationship. You are all alone on a lonely planet. That’s why you always need more. That’s why there’s never enough. That’s why neither man is quite good enough. That’s why you will never be good enough for any man, not without lies, not without the safety of a hedge, not without the reassurance that you know something he may never know, not without bamboozling the living fuck out of him.

Think about that. Love is a theft to you. You aren’t even feeling it. And you can only have enough if you take more than you actually deserve.

It’s time to turn the corner and get some clarity. In order to do that, you have to walk straight into your shame and self-hatred and look around at the world in your mind, a world where flaws are moral failures. You have to acknowledge your fear. You have to acknowledge how ugly and disgusting you feel. You’ve always felt that you had to put on seven veils and dance and charm and cajole just to have friends, or lovers, or support, or patience. You are a real living organism who can’t feel anything, so you’re pretending to be an invincible robot dog.

Once you start to feel, you’ll know that it doesn’t feel good to live a lie. Once you stop being numb, anesthetized by your fantasy world, you’ll realize that you are in a lot of pain. You will feel enormously, excruciatingly embarrassed. You will feel naked to the world. Your daring and your devil-may-care attitude will reveal themselves as swaggering cowardice. And you might end up breaking up with both men, so you can figure out where your imaginary world ends and you begin. It will be rough.

Stop and understand for a second I’m talking about something that might feel punishing at first, but it’s also incredibly beautiful: to see that you are the one being bamboozled the most of all, you are the one who feels defenseless, you are the one whose flaws seem to outweigh her strengths. That’s a moment of pure light. When you live in reality, you can say what you feel. You don’t have to dance on tabletops to feel seen. Seeing your shame clearly is the beginning of a new life, in a world where a church is a church and you can sing along and cry real tears and catch some glimpse of the divine. Feeling your pain deeply means standing up to read a poem in front of skeptical strangers and knowing that you’re at a poetry reading and not drunk at a rave or tied to the bow of a ship or stranded on a desert island. Your words tumble out and you know that you seem small to the world, but you feel big inside. You are trying to lift someone else up with your words. You are scraping yourself off the floor with your words.

Your humility makes love possible. Your vulnerability makes feeling your feelings possible. You are vacuuming your apartment for the fifth time this month because you love your dog. You are sending flowers to your mother because you know that will make her happy. You are standing in the middle of a large crowd, waiting for your kids to emerge from Harry Potter’s Terrible Quease-tastic Vertigo-rific Shake ’n’ Roll, and you are a little miserable, honestly, but when you see their faces, you’re so happy for them that it’s like you just rattled your own skull on a stupid ride right next to them. You are trapped in an overpriced, branded cement purgatory and you feel good.

That’s love. You are looking right at someone who is not perfect. You are feeling feelings for his dumb hesitations and stuttered sentiments. You are not all that sexy. You are not all that good. You are trying very hard to be better, and it feels like magic.


Order the Ask Polly book, How To Be A Person in the World, here. Got a question for Polly? Email Her advice column will appear here every Wednesday.

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‘I Love My Boyfriend, But I Can’t Stop Cheating!’