The Cheaters’ Club
From the moment that Spencer, in a white blazer and designer jeans, sauntered through the door of the swanky downtown Manhattan restaurant, I wanted to speak to him. From the time he chose the seat next to mine and started talking, I wanted to latch onto him for the rest of the evening. Long before we climbed into the backseat of his chauffeured car, I wanted to sleep with him.
By two a.m. I lay naked next to Spencer (as with others in this story, that’s not his real name), a devilishly handsome thirtysomething entrepreneur, on a couch in what felt like someone’s apartment but was an office that had been abandoned for the weekend. I envisioned our Happily Ever After scenario.
Then came his confession: “I’m married,” he said.
Had I ignored the ring subconsciously? There it was on his left hand, which was cupping my lower waist. I stared at the shiny gold band and started to think about Spencer’s wife: What was her name? What did she look like? Was she faithful to him? But it was surprisingly easy to look away. Instead, I focused on him, and on our instant connection.
That moment several years ago marked the beginning of a two-year affair, and of my interest in what social scientists call extra-pair copulation—and the rest of us call cheating.
According to Maggie Scarf, the author of five well-regarded books on adult psychology, the consensus among experts is that between 50 and 65 percent of husbands and 45 and 55 percent of wives become extramaritally involved by age 40. At the same time, according to a 2001 Gallup poll, 79 percent of Americans consider it “always wrong” for a person to engage in sexual relations with someone other than his or her spouse. To investigate this disconnect, I set out to infiltrate ashleymadison.com, a Web site devoted to facilitating adultery.
The Ashley Madison Agency is an online social network whose slogan is “Life is short. Have an affair.” (They have it trademarked.) Apparently plenty of people are heeding that suggestion, because the site has nearly four million members worldwide. Posing as a 27-year-old newlywed named Collette Cantrell, I decided to join them.
By getting to know a variety of people who use Ashley Madison, I hoped to explore a few thorny questions: What kind of men seek out illicit relationships online? Can adultery be a healthy way to fulfill one’s needs without alienating one’s partner? Is cheating really as bad as society makes it out to be?
Using my coquettish pseudonym, I purchased a basic Ashley Madison membership for $49. (The most expensive membership, the Affair Guarantee Package, costs $249 and offers a refund if you don’t find someone within three months.) After settling on the personal tagline “Seeking an adventure,” I completed my profile by writing a few sentences about myself and checking boxes in three categories: (1) Preferences and Encounters I Am Open to (spanking, erotic tickling, sensual massage); (2) What Really Turns Me On (stylish/classy, sense of humor, disease-free); (3) What I Am Looking for (shopping for sexy clothes/lingerie, daring rendezvous). I uploaded a photograph of myself and created a “private showcase” with additional shots.
Within a few days, I was sitting on 100 or so e-mails (as of this writing, that number is well over 1,000). Granted, many of these were merely “winks,” or notifications about being added to someone’s list of “favorites.” Others were “keys” granting me access to members’ private showcases, the contents of which ranged from headshots to bare asses, to women performing fellatio. The onslaught of attention was strangely gratifying, even if some of it was weird, and even if, as I later learned, the ratio of men to women on the site is nine to one.
To narrow my pool of suitors, I immediately eliminated anyone with a user name like “SexRus69” or who had used one of the site’s formulaic templates to contact me. Soon I settled on three candidates. Each was new to the site, in his late 30s, and physically attractive—and each had written me a personal note while refraining from sending me a picture of his erect penis.
To begin with, I reached out to Thomas, an Oxford-educated Brit who used my favorite sign-off: cheerio. As we shared our thoughts on marriage and relationships over e-mail, I began to feel a sense of intellectual kinship with him. We agreed, among other things, that monogamy is an unreasonable expectation, and that while others should be free to pursue their dull, suburban ideals, they shouldn’t impose their prudish views on the rest of us.
As our exchanges became more frequent and more intense, I found myself eager not only to see Thomas’s next message but also to meet him in person (he pressed for this, but he never pushed).
Thomas answered all of my nosy questions. He told me he was happy with his wife, and said he advises friends that when it comes to marriage, “if the person is a good buddy and you enjoy a good shag, then that’s as good as you’re going to get.” In his opinion, this is not cause for dismay; it’s a simple fact of life. Thomas admitted to having had several affairs already (though none with people he’d met online) and called himself a “big believer in monogamy through adultery.” His view—one he shared with his partner, allegedly—was that it’s unwise to “pull down the shrouds” with the unhealthy aim of knowing everything. Thomas guessed that his wife had cheated on him, but this thought didn’t trouble him; nor, he professed, would the idea of his affairs torment her.
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As the weeks went on, we shared our thoughts on New Yorker articles, David Foster Wallace, and the poetry of John Donne (his favorite line: “Full nakedness; all joys are due to thee”). We also discussed Brazilian bikini waxes, the “lost art of the hand job,” orgasms, and favorite body parts. Thomas said his pulse quickened when he wrote to me. Our blossoming relationship was a pleasant distraction from day-to-day troubles; it didn’t feel wrong or dirty, but natural.
Eventually, Thomas insisted on trading explicit photographs. He wanted a picture of me splayed across my bed wearing nothing but a coy expression. Wanting to please my cyber-beau, I seriously considered taking the shot, but ultimately I chickened out—in the age of the Internet, who knows where it might end up?
Our relationship fizzled, but with no hard feelings. In fact, Thomas wrote to me a week or so later, wishing me well in my Ashley Madison endeavor. Like Spencer, Thomas seemed perfectly able to have an affair cavalierly, rationalize it easily, and live happily.
The next man I met was significantly more conflicted. Jackson, as I’ll call him, wrote in his first e-mail to me that he had dithered over the prospect of having an affair throughout his decade-long marriage. He finally surrendered to the idea after reading about Ashley Madison in The New York Times.
Jackson’s early messages dripped with guilt and paranoia. He emphasized what he called a Mutually Assured Destruction Pact, asserting that he had too much at stake (i.e., three kids) to let anything get out of hand. Jackson also took such precautions as paying for his membership by money order, clearing the history on his Web browser routinely, and buying a spare phone for communicating with me.
Mindful of my experience with Thomas, I suggested an in-person meeting with Jackson rather than waiting until we reached the point of nude-pic request.
Early one Friday evening, I rode my mint-green bicycle to Grumpy Café on West 20th Street, dressed in a short floral dress and loafers. I was somewhat apprehensive that Jackson might expect an impromptu bathroom-stall romp, but mostly I felt torn between possible icebreakers (“Greetings, fellow adulterer!” versus “Iced coffee or hot?”).
Jackson had advised me that he’d be wearing green cargo pants and a light-pink shirt, adding that if I didn’t think he was “the one to feed [my] hunger,” I should feel free to make a stealthy exit without approaching him. That remark made me wonder if he’d be as handsome as he looked in his photos, but once I saw him, any concerns I had about his appearance vanished. Indeed, Jackson was everything he had claimed to be: bright, well educated, and financially successful—and sexually starved. I, too, was everything I’d claimed—a Georgetown graduate and bond trader turned writer who likes to read and ride her bike—save for one crucial detail: I was actually unmarried and unattached.
“Why me?,” I asked. “What are the other women on Ashley Madison like?”
“Well, for one thing, your skin is the color of purity,” he said, as if admitting his darkest secret. “It gets me thinking about the irony of finding you on some filthy cheater’s Web site. It doesn’t match.”
“So I embody a contradiction,” I said, aware of my starring role in some hard-core porno playing in the back of his mind.
“Yes. I love it.”
“And the other women, how did they seem?”
“I got some weird messages—women whose husbands wanted to watch and women who wanted to be peed on. That type of stuff.”
“Sounds like my competition was tough.”
“You definitely stood out … So what do you want, sexually?”
“We’ll get there,” I assured him. “I want to know if you’re happy.”
“Are you?”
“I asked you first.”
“I don’t want to disrupt my life,” Jackson said in a monotone voice. “I have three little ones. I want to wake up at home, to cries of ‘Daddy!’” After a brief pause, he added, “But my wife, she’s so conservative. She doesn’t fuck me, you know? Like really fuck me.”
“How conservative? You didn’t exactly answer my question, by the way.”
“She thinks watching porn is cheating,” he said.
“Yikes. How often do you have sex?”
“Never!” he exclaimed with a mix of bafflement and hostility.
“I’m sorry.”
“Are you happy with your husband?”
“Ummm … ” I stalled while conjuring my fake life. “Happy enough. I mean, we do have sex. It’s just that we married so young.”
“Well, just think about this: It only gets worse. It’s been downhill since day one for me. And I can’t imagine the rest of my life like this, let alone any worse. I can’t live this lie forever.”
“And you won’t consider divorce?”
“Kids. So tell me, what do you want sexually?”
“You first.”
Jackson eagerly listed a host of sexual positions and described various fantasies, none of which were outlandish. He wanted to experiment with a vibrator and sex toys, to be seduced by a woman in lacy lingerie wearing deep-red lipstick, and, on occasion, to be awoken by oral sex. He followed up this recipe for fulfillment with complaints about his wife’s shortcomings in bed. She doesn’t know how to move her hips, he said, and was apparently never briefed on the all-important Avoid Teeth While Performing Fellatio rule. Still, Jackson insisted, “my life is absolutely perfect, except for the gaping wide hole left by lack of sex.”
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“Why not visit a prostitute, then?”
“Never. Never have, never would,” he said. “I need some degree of intimacy.”
“And have you expressed any of this to your wife?”
“No point. Remember—porn is cheating.”
“Right,” I said, although I was beginning to feel for his wife—how could she satisfy him if she didn’t know anything was wrong? “What about therapy?”
He shrugged off the suggestion.
I’d warned Jackson that I had to be somewhere by seven p.m., so our first encounter was brief. It ended with Jackson pleading with me to get Skype so that we could masturbate together and inviting me to join him in Montreal, where he would be on business later that week (the $1,500 flight and the room at the Ritz would be his treat). The open-mouthed kiss he planted on me in public took me by surprise, but he seemed fully immersed in our escapade by then, his pent-up sexual energy at a boiling point. Meanwhile, I felt a little bit scared—not because Jackson was too aggressive, but because I was truly attracted to him. I kind of wanted to go to Montreal.
What stopped me from flying to Canada was the shame that Jackson projected, and the fact that he hadn’t exactly exhausted his other options, refusing to talk to his wife or a therapist. Whereas Thomas and Spencer seemed at ease, as if they were abiding by the terms of unspoken agreements with their wives, Jackson’s actions reeked of deceit. Then again, Thomas and Spencer may simply be smoother adulterers. Whatever the case, I refused Jackson’s next three weekly invitations to travel with him. As an excuse, I could easily claim that it was difficult for me to get away from my imaginary husband.
For the sake of my experiment, though, I obliged Jackson by conjuring up several explicit “visuals” via e-mail while he was away. I also participated in a few rounds of real-time cyber-sex, despite confusion over the whole typing-while-touching thing. The transcripts of those e-mails and conversations make me laugh, cringe, blush, and feel aroused all at once, but they’re way too graphic to print.
I managed to hold Jackson’s interest for weeks without sleeping with him. Our relatively innocent relationship was an outlet for his sexual frustration and, he said, gave him plenty of material to masturbate to (something he did in the shower, hurriedly, so his wife wouldn’t get suspicious).
Though we stopped short of fornication, I’d say it was a moderately successful Ashley Madison adventure for Jackson. I still wonder whether his wife might loosen up if she were presented with his honest sentiments. But assuming she is in fact uninterested in sex, wouldn’t everyone be better off if I were to quench Jackson’s lust without his wife’s ever knowing about it? Wouldn’t it make him happier and, in turn, make her happier? Is it so far-fetched to think that Ashley Madison could be the answer for Jackson?
For my third test subject, I settled on Leonard, who said he was in a serious but “open” relationship. His profile boasted: “I promise you won’t be disappointed. Handsome, smart, funny orthopedic surgeon. I’m looking for a nice lady to enjoy occasional dates and sexual fun.” He sounded a bit conceited, but my interest was piqued, and I replied.
Following a few brief e-mails, I met Leonard for a drink at Olives, the restaurant in the W Hotel in Union Square. I wore a short gray dress with a white tee underneath. Leonard said he’d be in black pants and a caramel-colored button-down. Fortunately, I responded appropriately upon hearing the name “Collette” called outside the restaurant. Only then did it occur to me how terrifying it would be if someone I knew were to spot me and call out my real name during one of my Ashley Madison dates.
In person, Leonard was a lot smaller than advertised. His “private showcase” photos must have been taken years ago, after a six-month-long creatine diet. As it happened, I liked the way he looked in person better, but the casual act of deception put me on my guard.
He sat down, and I asked Leonard about his career: “So, you’re an orthopedic surgeon?”
“Nope,” he replied. He actually specialized in a slightly less impressive branch of medicine. “I wrote that because I don’t want my colleagues or patients to know I’m on the site,” he explained.
“Oh, O.K.,” I said, uncomfortable with this, his second lie.
“So maybe I’ll start,” he offered after a sip of his vodka soda.
The speech that followed seemed well rehearsed. Leonard had been in a relationship with the same woman for several years, he told me, and they had tried both monogamy and something closer to “friends with benefits.” Currently they abide by a strict set of rules (as elaborate as a Donald Trump pre-nup, it seemed to me) that allow them to see other people but still maintain a committed relationship. Leonard believes this lifestyle works because neither he nor his girlfriend is interested in getting married, and neither wants children (he had a vasectomy in his late 20s).
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“So why didn’t monogamy work?,” I asked.
“For me, the problem is that she’s difficult to please.”
“You mean she doesn’t orgasm easily?”
“Exactly.… It makes me feel like less of a man, truthfully … I want to be able to please someone in more than one way. But I do love her. And I’m happy with her as my primary partner.”
“So how’d you hear about Ashley Madison?”
“Howard Stern,” he answered.
“Right. And why’d you contact me?”
“You were just one of the girls who popped up on the home screen when I logged on one day.”
Leonard certainly knew how to make a gal feel special. We finished our cocktails and chatted a bit more before parting ways. In the following days, he called and wrote me several times to propose getting together again, since we’d “clicked” so well. I don’t know if that means I’m a decent actress or Leonard is utterly oblivious, or both. Maybe what turned me off about Leonard was my suspicion that he is in part responsible for his girlfriend’s problem. He came off as arrogant and clueless, two traits that rarely go along with sexual aptitude. As for his open relationship, to me it seemed more regimented than liberating.
The three men I met through Ashley Madison were very different, but they all had a common goal. That goal might strike some people as depraved, but I don’t think Thomas, Jackson, and Leonard are bad people. Those who remain faithful to their partners—whether out of religious conviction, prudence, lack of libido, or supernatural willpower—might deserve praise, but their ability to repress their baser instincts does not make them superior in my eyes to people who indulge theirs. I don’t wish to champion adultery, but the notion that strict monogamy is the right path for everyone strikes me as narrow-minded, even holier than thou.
I know from experience that affairs don’t have to destroy the lives of everyone involved. A successful dalliance, if such a thing exists, requires candor and discretion—two things Ashley Madison specializes in. Spencer and I remain friends to this day, and he knows about this article. He was forthright about having built his life with someone else, and about the fact that he couldn’t, or wouldn’t, give me what I needed. Sure, there were times when I felt lonely, exploited, and neglected. But I knew what I was getting into.
If and when I find a life companion, I can’t say with certainty that I’ll be 100 percent faithful—not because I don’t want to be, but because it seems presumptuous to assume that strict monogamy is my fate when the majority of people who attempt it fail.
Maybe I’m jaded. Maybe, as some social scientists would say, I’m a sex addict incapable of achieving healthy intimacy. Or maybe, as Dr. David Barash suggests in his provocative book The Myth of Monogamy, when it comes to marriage we ought to apply Churchill’s maxim about democracy: among lifestyle choices, it’s the worst possible option except when you consider the alternatives. 
