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Cheatingland

The Secret Confessions of Men Who Stray

About The Book

Reminiscent of Three Women and The State of Affairs—and based on years of research and in-depth interviews with more than sixty men—this eye-opening and explosive study explores why men cheat, how they do it, and the repercussions that infidelity has on every aspect of life.

It is estimated that one in four married men cheat on their wives. Of those, roughly half claim that they are “very happy” in their marriages. So why risk ruining it all? Is it the sex? The affirmation? The danger? Yes, it’s all of that. But it’s also so much more.

The author of this book has conducted a series of in-depth interviews with men and women of all ages and backgrounds who have cheated in the past or are currently cheating on their spouses. They talked openly and intimately about details of their affairs, and the emotions that they experience before, during, and after.

The book breaks down the five major categories of cheaters, defines the typical cheater personality, and looks at how husbands can cheat while also loving their wives. It reveals the tips and tricks spouses use to get away with secret affairs and examines everything from the influence of cheating parents on their children to the possible outcomes once an affair is discovered. This unfiltered window into the hearts and minds of men explores the psychological roots of cheating and proposes a new vision of masculinity that is more emotionally aware and could significantly change relationships for the better.

Excerpt

Chapter One: Into Cheatingland CHAPTER ONE INTO CHEATINGLAND
I was sitting in the locker room after a workout, talking about nothing with the guys, when someone I’ll call Adam kicked opened the door to another world. He looked around the room to make sure no one would overhear him and then—in a tone you’d use to tell your friends about a bank heist you’d just pulled off—he said, “I got a new girl.” His spine straightened as if a pulse of electricity had zipped through it.

“We were in the Hilton yesterday. She is crazy! The sex is insane!” He said things had been building for a while. “We’ve been flirting for years, okay, and nothing ever happened until one day it just… happened. We know it’s wrong. But the sex is ridiculous because it’s grimy.” This guy knew he was playing with fire, and he liked that. Breathlessly, he went into detail about their wildest sexcapade. Meanwhile, Adam’s wife was sitting outside, waiting to drive him home.

“The other day my girlfriend parked her car down the street from my house and waited for my wife to leave to go to work.” We were hanging on his every word. “As soon as she saw her drive away, she pulled in. My heart was beating so fast it was crazy.” After Adam finished his story, everyone walked out of the locker room, said hi to his wife, and gave her hugs, as if nothing unusual had been said.

A month later, another friend invited me out to dinner, saying that he had something he wanted to show me. I arrived at the restaurant to find that he had booked a table for three. Then he strolled in beaming with pride because he had a woman on his arm. I had dinner with him and his girlfriend of three months while our wives were at our sons’ evening martial arts class. His girlfriend was also married. They weren’t even considering breaking up their respective homes, but they enjoyed each other and loved the thrill of their clandestine relationship and their intense sex. The action took place in an apartment they’d slip off to after work, a place she referred to as “Cheatingland.” She made it sound like Cheatingland was a clandestine little country with its own customs—sort of Fantasy Island, where wedding vows were forgotten and normally mild-mannered people could morph into sexual beasts.

After those two encounters, I started thinking about how many men I knew who had cheated on their wives. I thought back to all the men who had whispered or crowed about what they’d done and all the men I’d heard about who were running around in the shadows with women they weren’t married to. I realized that there are a lot of men ducking in and out of Cheatingland. It seemed to be pretty common even though it was an extremely dangerous place to visit. The risk of ruining one’s marriage, if not one’s life, was really high—I knew people who’d been caught cheating, and it destroyed their families—so what were the cheaters really looking for that was worth the risk? If it was just about sex, you could hire a prostitute, but these men were not doing that; they were chasing and sleeping with women who weren’t professionals. I began wondering what sort of man would do that. Is there a type of man? Are there certain traits that link men who cheat? How did they keep from getting caught? And what happened when they did get caught?

I thought about the ones I knew. They seemed like a unique breed, many of them egotistical, brash, bold, thrill seeking, and hypersexual, with lots of what millennials call Big Dick Energy. But there were significant differences within the group. Some guys had been crazy when they were single and kept it up when they were married. Some guys seemed like they were trying to make up for lost time after having been not all that successful with women before they were married. Some were in unhappy unions, but plenty of them lived in happy homes. I knew men who loved their wives immensely but were nonetheless willing to leap into bed with someone else and saw no contradiction in that. There’s a Russian roulette aspect to all of it: some men get away with it for years, while others get caught and ruin their lives. Most husbands don’t cheat on their spouses, but lots do, and a lot more men get away with it than wives realize.

But what’s the real reason why men cheat? Is it really about the pursuit of sex or the thrill of the hunt, or is there something missing from their marriages that they are trying to find elsewhere? Or is it some void within themselves? Is sex enough, or do they need a relationship, too? Are they getting revenge on their spouses? Have their wives done something wrong, or are some men simply socialized to be unfaithful despite that wedding band on their finger? Are they trying to prove something to themselves? Searching for a new partner? Do they just want to have more than one woman? Or was there some emotional need they were trying to fulfill? The more I thought about the men I knew, the more I realized I knew almost nothing about this behavior that so many of them were engaging in.

As a society, it seems like we can’t stop talking about cheating. It’s a theme in countless movies, TV shows, songs, and novels. Forbidden sex is steamy, seedy, titillating cultural catnip. And it’s not just in the culture: go to any cocktail party, have a few drinks, and get deep into a one-on-one with someone who feels like he can trust you, and odds are he’s got a cheating story to tell, either about a friend, or about their spouse, or about themselves. Most people think cheating is wrong, yet a lot of folks are doing it.

Having an affair fills every day with danger: one wrong move, one wrong word, and a cheater’s life might explode. No one wants to hurt his spouse. No one wants to lose his kids. No one wants to be the reason why his family fell apart. And yet people keep flocking to Cheatingland partly because the combination of lust and risk plugs a relationship into a high-voltage electric outlet. The person you’re not supposed to talk to, not supposed to be alone with, not supposed to be having sex with? That person can be insanely alluring precisely because she’s off-limits. Many people dismiss men who cheat as dogs and women who cheat as whores, but there must be more behind the choice to cheat than a simple lack of character or an animalistic desire for sex.

As my friends’ stories about cheating swirled around in my mind, I wondered if it was possible to get guys to talk to me in depth about what they’d done. At least ten married men I knew had confided that they’d cheated at some point, but this was mostly bragging. Could I get them to go deeper, to go beyond chest-beating stories about hotel conquests and get into honest explorations of their souls and the reasons why they had left home to play? I was a little nervous even to ask—I wanted guys to drop the façade, the bluster, the ego, and tell me things they probably hadn’t told anyone, admit to a serious relationship crime, and explain their actions and motives in detail. Adultery is not against the law, but admitting to it would be more dangerous than copping to many illegal activities. It’s one thing to whisper to a guy that you’re banging a chick behind your wife’s back. It’s quite another to tell a researcher who’s recording your voice that you’ve slept around during your marriage. But I was compelled to know why they had risked so much and what their deeper whys were.

First, I called a few friends who had, in the past, boasted to me about things they’d done. Some were willing to talk further; some were not. I noticed quickly that asking a friend to talk about this topic when he wasn’t ready could mean losing the friendship entirely. Some said, “I told you that to get it off my chest, I didn’t tell you that for you to remember it and bring it up later.” So, I began reaching out to friends of friends—people I didn’t really know. That one degree of separation provided them some feeling of security, but having a friend in common also provided some trust.

The more men I found and spoke to, the more intrigued I became. Guys told me crazy stories, but they also told me about their motivations, their ways of justifying cheating, their ways of hiding it, and what their ideas about masculinity had to do with all of it. What started out as a personal curiosity and a handful of conversations suddenly became a more rigorous investigation: I would call as many men as I could and ask them similar questions. Then I would try to steer them into talking about their hows and their whys.

When men talk to their friends, they keep up their guard. It’s not a time to be vulnerable, but to show how cool and untouchable they are. Men will talk to their friends about their mistresses in ways that make them sound like sexual swashbucklers, without ever approaching the internal void or the existential pain that sent them out seeking a secret partner in the first place. Men’s default position is to avoid diving into their emotions. So I had to probe while at the same time creating a safe space for them to share. I had to make them feel heard and unjudged and get them to trust that even though I would be telling their secrets, I would protect their identities. They wanted to talk about the madcap things that happened in pursuit of extra women—I listened even though there’s not much to gain there in terms of insight about the cheater’s psyche, but sometimes you have to let men tell you their favorite stories and go on a bit about how great they are before they can shift into the self-analysis I needed. So, my interviews took time. Most men weren’t going to talk deeply about themselves without my creating the right conditions first.

After I interviewed some friends of friends, they introduced me to a few more men who’d cheated—everyone knows at least one guy, it seems—and the list grew. I viewed this as a project for exploring the thoughts, feelings, and behavior of men who step out on their wives. I would function as a sort of anthropologist reporting from inside the wildest corner of the proverbial male locker room. I wanted to peer inside the minds and souls of these men without condemning them, because, for one thing, that’s too easy, and, for another, if I did, they wouldn’t open up to me.

I wanted to know if they were in love with their wives. I wanted to see if they were disappointed by the institution of marriage itself, with its claims of true love being the answer to life’s problems. I wanted to gauge the impact of the toxic expectations of masculinity: the boys-will-be-boys culture that views women as yet more toys to be acquired. I wanted to know if they see manhood as something that must be proven endlessly through repeated feats of masculinity, strength, sexuality, adventure, risk taking, power. Was it that guys were bored with their lives? Were they desperate for a break from adulthood? Did they want to return to a younger version of themselves? Was it their wives’ fault? Could a wife do anything to stop her husband from straying? I asked questions, and more, of men who’d cheated. Their answers surprised me.

Society doesn’t incentivize men to talk about their feelings. But I believe that I was able to get those I interviewed to open up and share their feelings and their stories and get down to the roots of how they feel about cheating. I undertook to change all names and many identifying details, and ultimately decided that I should be anonymous as well. While I have made many changes in details, I believe that I have preserved the essential reality of my informants. Importantly, I am presenting not portraits of specific individuals but the exploration of a landscape, an MRI of the cheating heart in general, in order to give you a better understanding of the phenomenon.

As we talked, the men seemed to open up about their experiences and feelings. Many times we got down to their most honest whys. They talked about themselves, their wives, their past girlfriends, their mothers, their fathers, their insecurities, their vulnerabilities, their anxieties, their doubts, their fears.

A lot of men remarked on what they felt was an unusually personal conversation. “This is like a therapy session,” one said. Another said, “I feel like I’m in a psychiatrist’s chair.” Another: “I owe you two hundred dollars an hour.” Many thanked me for the chance to talk about themselves in an unvarnished way that let them pour out their truths and explore themselves. At least one person said our conversation changed his life—after we hung up, he was overcome with the feeling that he should confess to his wife. (And he did. But we’ll get to his story later.) Man after man said he’d never had a chance to open up about this topic, and many seemed relieved to be able to finally explain themselves. Many said they had admitted more to me than they had ever admitted to themselves.

As I moved through my first thirty to forty interviews, I resolved to talk only to men, because I envisioned this as a study of male behavior. But as my research progressed, I realized that I could probably learn more by also speaking to women who committed adultery. They could help me better understand men who cheat because their thoughts and experiences would add valuable context, allowing me to see how women’s experiences regarding infidelity were similar to men’s and how they were different. So, I began to search out and find women, both straight and lesbian, who had fascinating stories. They would become critical voices within this study. Frankly, the women were more forthcoming as well as more insightful. Most of the women I spoke to found it much easier to access their feelings—their whys. Women revealed that, for them, cheating is far easier to pull off than men would ever imagine, and, sometimes, it plays an important part of self-discovery. Much more about that later.

Some of the most powerful contributors to my study were lesbians, but gay men were a different story. Even though I wanted to include them, it proved tricky. I made an effort to find those voices, and, yes, there are a small number of gay men among my subjects, but most of the gay men I spoke to admitted they slept around but also said they viewed monogamy as elastic. Neither they nor their partners regarded such behavior as cheating. I was told that, for many gay couples, it’s not unusual to accept partners having sex outside their relationship as long as certain ground rules are followed. The rules differ for each couple, but examples include “Don’t fall in love,” “Never have unprotected sex,” “No sleeping with anyone your partner knows,” and “Be home by two in the morning.”

This was extramarital sex, but not cheating as per my definition, for cheating requires secrecy. It’s not condoned within the relationship. Otherwise it’s an open relationship. I didn’t interview people who said they were in open relationships—that’s an entirely different entity. Open relationships are a fascinating reshaping of the traditional boundaries of marriage, but I wanted to explore something else. I wasn’t interested in talking about extramarital affairs that were partner approved. I wanted to know about affairs where everything was at stake.

It was painstaking work to find more and more people who would talk, but over a four-year period I interviewed sixty-one men and twelve women, each for at least an hour. I also spoke to numerous psychologists, sociologists, and sexologists for their insights and context. In the end, less than one-sixth of my subjects were people I knew before I began the study. Most of my interviews were conducted over the phone. I asked each to give me their first name only, as well as the city or region they lived in, their age, race, and general area of employment.

I collected this information to make sure I had a broad cross section of people from a variety of regions, races, and social classes. My volunteers are a diverse group: white, Black, Hispanic, and Middle Eastern. They range in age from the early twenties to the midsixties, with most falling between thirty and fifty years old. They include real estate developers, sales reps, truckers, teachers, body shop managers, stand-up comics, attorneys, nurses, software consultants, restaurateurs, and more. They’re from Atlanta, Baltimore, Boston, Detroit, Houston, Indianapolis, Las Vegas, Los Angeles, New York, San Antonio, and beyond. Some had one long affair, some had several short affairs, some are currently in affairs, and some got caught or quit the cheating life on their own.

I could not find many of my interview subjects again even if I wanted to. For many, anonymity was important to giving them the freedom to be brutally honest. I asked them if they had cheated, how many people they had been with, why they had done it, who had influenced them, how they pulled it off and what they did to get away with it, whether they had been caught and what they’d done after getting found out, whether it was all worth it, if they felt guilty, and much, much more. Everyone wants to tell his or her secrets; you just need to give people the space to do it safely, including that they wouldn’t feel judged.

As I worked through my research, several subjects pushed me to reshape my definition of cheating in one critical way. When I began my study, I defined adultery as having sex that was kept a secret from your spouse. I wanted to talk to people who needed it so badly that they snuck out the proverbial back door, broke their vows, risked divorce, and then returned home. But as I met more and more women who had cheated, many of them said they were involved in clandestine affairs that felt wrong morally—but these relationships were not sexual or physical in any way. Sometimes they called these “emotional affairs.” It’s telling that very few men acknowledged being involved in this kind of extramarital relationship.

At first, I wasn’t going to include these stories because I was stuck in the perspective that cheating required a physical component. But as I listened to story after story of emotional affairs—deep, secret connections with someone outside your marriage, where there are feelings, flirting, and the intensity of a furtive relationship even though there’s no sex—I realized that quite often there is no substantive difference between emotional affairs and consummated ones. People, especially women, who engage in emotional affairs regard them as a marital violation and refer to them as cheating. They are taking the same risks, experiencing the same sense of danger, and getting most of the same returns as people in sexual affairs: the thrill of being in an illicit situation, the psychological exhaustion from pursuing the relationship while keeping their spouse in the dark, and the accompanying guilt that induces.

After hearing many stories of emotional affairs, I realized I had to redefine cheating to decenter sex and instead see it as a secret relationship that is not necessarily sexual yet is still sexually charged. You don’t have to sleep with someone to be cheating. You can devastate your partner even without touching someone else. For many people with a partner who was unfaithful, finding out that he was in an emotional affair can be even more painful because it’s not just meaningless sex, it’s a genuine connection. One woman said to me, “I’ve been cheated on, and I’ve forgiven a partner for cheating on me. If it was purely physical, I’m, like, ‘Okay, I’m not going to forget this, don’t make a fool out of me, but I can move past that.’ But emotional infidelity is a lot worse. You’re sharing really heavy romantic words and ideas, and it has elements of love and romance. That right there, oh, man, that there can crush you.”

It’s easy to pass judgment on a two-timer. He’s violating his vow to the most central person in his life. He’s risking hurting his spouse immensely. He’s jeopardizing the future of their family. And for what? Selfish pleasure? Isn’t adulthood supposed to be about sublimating the imperative to constantly please yourself and instead act as if you’re part of something bigger than you? Aren’t you supposed to put what’s best for your spouse and your children ahead of your own needs? The desire to condemn cheaters is understandable because adultery isn’t a victimless crime. People have lost the unit that shaped their childhood or their adulthood because of an affair, and that can have a devastating impact. Some men have used affairs to demean or control women.

But in order to find out why people stray, I had to put aside judgment. One man who had a string of girlfriends while his wife was at home with their three kids asked me, “Do I sound like a monster?” I told him, “No, you sound like you.” Admittedly, he did sound monstrous for fooling around while she was drowning in responsibility and diapers, but I had to give him the freedom to answer my questions the honest way he wanted, no matter how ugly it was, because without that I couldn’t uncover his true self and his real reasons for cheating. Once we established that, we could get down to ideas that might help people understand better why and how cheaters cheat.

I’m not saying that we all need to learn to accept cheating. Every situation is different, and every person will respond in his or her own way. Some people will uncover an affair and flee the marriage. Others, despite their hurt, will find a way to reshape the relationship and forgive. Either way, I hope this book can help people think through and comprehend the real reasons why a cheater makes certain choices and what to do with that knowledge.

Many couples survive the revelation of an affair. I will talk about how they did that and what cheaters need to do to save their marriages. For now, just know that I was able to get people to tell me truths that they’re not willing or able to tell their partners, so if you’re trying to understand infidelity in your own life, hopefully you can use this book to bridge the gap between what someone is able to communicate and what the rest of the truth may be. This book can help you see the underlying feelings cheaters have had, so that you can understand what it was that led them astray. Whether you choose to end things or move forward as a couple is up to you, but with more perspective, you may approach your decision with greater clarity.

How many Americans are cheating? It’s hard to really know because a lot of people get away with a lot of cheating. In fact, it’s possible that most infidelity is never discovered. Many men told me they never got caught. The old adage that the wife always knows is definitely not true. And women find it even easier to evade detection. But large surveys conducted over the last few decades have concluded that, in the United States, about 20 percent to 25 percent of men have cheated on their wives, while approximately 15 percent to 20 percent of women have cheated on their husbands. Several researchers have found that in about half of all marriages, one partner will cheat at some point, and in roughly one in five marriages, one partner is cheating right now. According to some recent studies, increasing numbers of married women are cheating, and if you include emotional affairs, some researchers say women today are seeking intimacy outside of their marriage about as much as men.

Modern technology only makes it easier to commit adultery by connecting strangers through social media sites such as Instagram and Facebook or websites created specifically to facilitate affairs, including Ashley Madison and AdultFriendFinder. There are more ways to meet someone who’s not in your everyday social network than ever before, and that expands the number of opportunities for cheating infinitely.

Cheatingland is like a grown-up’s amusement park where you can get lost on the erotic rides, find an ego boost, indulge in unapologetic debauchery, forget about the outside world, and step outside your real life for a little while. In contrast, Marriageland, on the other hand, is like the parking lot outside the circus. It’s mundane, like feeling tired from the long day and having to struggle to find your car amidst a sea of other vehicles in the train station parking lot. It’s tedious, like navigating through bumper-to-bumper traffic to get to the freeway. But it’s also joyous, as when everyone is laughing and singing songs together at the top of their lungs on the drive home, creating bonding moments that will stay with all of you forever. For most of us, Marriageland is what makes life worth living. It provides the stability, the balance, and the support that help you get through the days, it carries you through the tough times, it helps bring fun to the smallest moments. But despite the immense danger of losing your place in Marriageland, some people still find themselves lured toward Cheatingland. This book will help you understand why.

The next chapter looks at how husbands can cheat while still loving their wives and examines some of the core influences behind cheating. Chapter 3 unveils the five major categories of affairs and weighs the differences between them. Chapter 4 dives into the women of my study and their perspectives. Chapter 5 explores the typical cheater personality. Chapter 6 is about the many tricks and tactics that unfaithful spouses use to get away with it. Chapter 7 shines a light on the dark side of cheating—what happens when things go horribly wrong. Chapter 8 examines the reasons why some men quit cheating. And chapter 9 goes into what options cheaters have if they get caught.

In my talks with male adulterers, I heard a lot of things that men would never tell their wives. Chris from Chicago said at the end of our interview: “I guess women would be very frightened if they heard the conversation we just had. My wife would probably faint and have a heart attack if she heard, but the thing she wouldn’t understand is what’s really in my heart.”

This book is here to tell you what that is.

About The Author

Anonymous is a journalist who has spent a decade investigating the topic of men and infidelity. He is married with children. 

Product Details

  • Publisher: Atria Books (March 22, 2022)
  • Length: 256 pages
  • ISBN13: 9781476705781

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