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I went undercover on Ashley Madison to find out why women cheat

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BY CHARLES J. ORLANDO

"Honey, I have to join Ashley Madison.”

So began the pitch I gave my wife to let me join the marrieds-looking-for-affairs website, AshleyMadison.com. It would be part of my research into women who cheat, why infidelity is increasing, and what can be done to possibly affair-proof a marriage. I proposed to “cheat” on her for a few weeks, to talk to and attempt to seduce as many women as possible, and get a real-world understanding of why women want to stay married but also need some illicit action on the side.

Of course, on my end, there’d be nothing more than conversation. She looked at me straight-faced, unflinching. I searched her eyes for any telltale sign of the Charles-I’m-going-to-punch-you-in-the-face-right-after-I-castrate-you look; nothing. After a long pause, I got her only thought: “No, I get it,” she said emphatically. “It’s a great story. But it’s kinda like asking the newly-vegetarian fox to guard the henhouse, isn’t it?”

I thought about it, and unfortunately her statement wasn’t too far from the truth. If you back me up a few years—sans wife, kids, dogs, published book on relationships and 400,000+ fans following my relationship advice on Facebook—I was a chronic womanizer. This is a past she knows about but never experienced personally.

To make matters worse, I wasn’t some weak pick-up artist using idiotic dating boot camp approaches that reeked of negativity and douchebaggery on vulnerable women in order to break them down and manipulate them into sex. No, I was far more despicable than that.

Was I looking to get women into bed? Of course, but it was more than that. I worked hard to become the embodiment of seduction. To quickly read the spoken and unspoken clues of what a woman was looking for in a man and then give her the perception I was that guy—in effect, to become so alluring that she would willingly give herself over, thinking that having sex was her idea. After all, it’s much easier to convince people of things they think they have thought of themselves. It was quite a rush, and as the wake of emotional destruction would later exemplify, seducing women became my drug of choice.

“No, babe, that’s not even close,” I told her, not fully considering the implications of the coming situations. “That was 15, almost 20 years ago. And you know that I love you. There’s nothing to fear.”

After another pregnant pause, she consented with a few words of sage advice: “Don’t fuck up.”

The Statistics

According to The Journal of Couple and Relationship Therapy, nearly 50 percent of married women and 60 percent of married men will have an extramarital affair at some point in their marriage. When you consider that these statistics are nearly double what they were a short 10 years ago, clearly this is beyond an issue; it is now commonplace.

But it’s far from a surprise; it was predicted.

Futurist Alvin Toffler wrote the best-seller Future Shock in 1970, and with matter-of-fact conviction he wrote of “trial” or “temporary marriages”—young people’s first marriages, lasting three months to three years—and of “serial marriages” that would take place after the dissolution of the “trial marriage” at specific turning points in people’s lives.

So, does this mean marriage has “jumped the shark” and become obsolete? Hardly. Marriage is not the issue. Commitment and loyalty or the lack thereof are at the crux of this. After all, marriage is a legal and/or spiritual binding of two people, but if commitment isn’t there and loyalty becomes a matter of subjectivity or convenience, the marriage is already nonexistent. Cheating then becomes a symptom of a secretly failed marriage.

But is it really so black and white, with no grey and no room for mistakes, missteps, or moments of weakness? Do people who cheat want to leave their current marriage? Are they secretly trying to get caught so they’ll have an excuse to get out? I needed answers to these questions (and many others), so I headed where any high-tech junkie looking to cheat on his wife would go: online.

The Business of Infidelity

The advent of the Internet has made having an illicit affair easier than ever before. Meeting Mr. or Ms. Right, The Sequel, is a mere mouse-click for anyone with a credit card. If you’re looking to hit-it-and-quit-it, there’s AdultFriendFinder.com, Craigslist’s Casual Encounters or Fling.com (among many others). But sex-only semi-anonymous hookups wasn’t where my investigation was headed, as women looking to merely have sex can meet a man anywhere—nightclubs, coffee shops, Facebook, wherever.

My hypothesis was simple: women who were looking for an extramarital affair with another married man were looking to connect in some way. If both parties were married, they not only started on even ground, but they had something in common—they were missing something from their current relationship. I needed to uncover the motivations behind starting and maintaining an affair.

And affairs are big business. Numerous websites are dedicated to connecting those looking to engage in flagranté delecto sans spouse. AffairsClub.com, MarriedCafe.com, LonelyWivesAffairs.com are but the tip of the iceberg, and all have women and men signing up in droves.

The undisputed leader for cheating is AshleyMadison.com, the “life is short, have an affair” website. AshleyMadison has experienced meteoric growth since its founding in 2002, with no slowing in sight. And while founder and CEO Noel Biderman doesn’t condone having an affair, he seems perfectly comfortable with others doing their infidelity thing.

Now it was my turn to get my (feigned) cheat on.

I filled out my nickname and relevant info, plopped down my credit card number (discretely billed as “AMDB” to my credit card statement), and then all I needed to do was wait. I was faced with the eternal online seduction dilemma: now what? What will make the opposite sex want me online? What do women want to see on my profile?

Recent reports state that Ashley Madison has a community that is comprised of 70 percent men and 30 percent women. Clearly women have the upper hand with choice, so I needed to stand out against all the other guys. I posted a real picture of me (I was looking to connect in-person, after all), but I listed a fake name (if they Googled my real name, I was sure to be caught). To formulate the right approach, I decided to do something I couldn’t do in the real world: get into the minds of my competition, albeit a little sneakily.

I signed up for a second Ashley Madison account as a woman, “Shelly,” and began checking out the guys’ profiles. Most of the men’s profiles highlighted attempts at humor, asking straight-out for sex to romance (“I like walks on the beach.”)

In contrast, so many of the women’s profiles were dripped with laments ranging from “lack of attention” to “seeking excitement” to “need someone who pays attention.” Additionally, it was fascinating to see “Shelly’s” inbox fill up in a matter of minutes. I hadn’t even added a picture or completed the profile for that persona.

With a firm understanding of where my competition played—and the miserable approaches of some—I got to work writing something unique and confident yet mysterious and seductive. I set up three profiles to see which would resonate the fastest and which would hit with the most success. “Scottie” was unsure, shy, and a bit weak (“I’m not sure why I’m here”), “Greg” was the quintessential Alpha Male (“You know you want me”), and the aforementioned “Cameron” was closer to the middle (“Too many men get comfortable—even complacent—and forget that foreplay starts outside the bedroom…that kisses can start soft with cheek strokes, but end with the back of her hair being pulled in wild passion”).

Early Success

Online dating is a complicated arena much like ordering fast food—in that what you get is never really what the picture and description promise. And given the demographical split on the site, I was prepared to be searching and waiting for a number of days for interest or responses. To my surprise, Cameron’s profile had 20 messages on his first night.

I responded to a few messages, and before I knew it I was invited to a chat session with “SexyCat” (profile name changed to ensure her anonymity). SexyCat wanted to know all kinds of things—and what I would do if given the opportunity.

With my wife watching TV on the couch a mere 10 feet away, here I was talking dirty to a 36-year-old married woman (whose husband was probably watching TV on the couch a mere 10 feet away from her). SexyCat wasn’t the only one. I discovered that to satisfy their deep longing for passion with minimal risk, many women sign up for Ashley Madison to have virtual sex via chat.

Over the next several days, I had chat sessions of varying length with 33 different women. In each session, I attempted to take things to the next level—an in-person meeting—but no-go. Most of these women seemed comfortable in getting what they needed online. It was arm’s-length cheating for them (and perhaps one-handed typing). I hope I didn’t disappoint them and that virtual cigarettes were ablaze in post-coital, pixelated afterglow of my cybersex adventures.

I told my wife about my hot chats, and she laughed. We got into a long discussion about the arm’s length approach to cheating these women had, and if it was really cheating. If it was borderline anonymous (read: they didn’t know much about me), it was akin to an interactive romance or erotic novel. I recounted some of the more sexually explicit material these ladies had written, as well as what I wrote in response. We both said aloud what we have known for a long time: When it comes to sex, women will get into the real detail, so much more so than most men. And with the inherent anonymity of chat, those inhibitions only grow exponentially. But I hadn’t been afraid; I can talk dirty with the best of them.

However, Ashley Madison had more in store for me than just chat sessions.

Date #1: “Ashley”

“Ashley” initially reached out to me and was eager to meet. After a brief inbox exchange on the website, we decide to meet for coffee at a cafe in Mountain View, a stone’s throw from California’s Silicon Valley. She was a dead-on match to her picture: a striking 5’8″ blonde. As we headed inside, I caught a glimpse of our reflections in the window and laughed quietly. At 5’5,″ I look like Dudley Moore to her Brigitte Nielsen.

She was confident, and as it turned out, a bit of a cheating pro. At 43, Ashley is a pure Type A personality, a Sales Executive in high-tech; she’d been married for 22 years and has had several affairs. Ashley Madison has been her “outlet” for the past number of years. I asked if her husband has an outlet, as well, and she was clear that he doesn’t. “He would never,” she said with equal confidence. “He doesn’t have time for this kind of thing.”

As we talked, our conversation turned to the philosophical and intellectual side of life and world events: Descartes, Nietzsche, politics, world history, religion and sex, subjects about which I have no shortage of opinions and personal insight. And I realized her outlet was mental and intellectual stimulation. She was fascinated that I was able to keep up with her, and she flushed, showing signs that this was more than banter for her—it was foreplay.

Ashley told me she loved her husband but couldn’t understand why he had dropped back from their relationship. He was commited to “passion and romance” when they dated but had recently become “all work and no play.” She shared briefly that as the Chief Technical Officer of a technology start-up, he was too busy for her, with travel and his company taking all his time. “But he’s always been too busy, ever since we got married,” she lamented.

I piled on to her discontent by falsely offering that my wife also has no time for me, but I then asked her: “So why don’t we leave them, then? Why are we here?” She didn’t miss a beat. “I need passion. I need to feel something, almost anything at this point. He has great qualities, but... We then dropped the subject at her request.

She was extremely intelligent and witty—and she was just as clear that sex was a priority.

“You seem a little green, so let me explain where I’m at. I’m not here looking for a husband, so you don’t need to worry about that. I’m looking for a man to take the lead; to invest his time, but not his emotions. Oh, and your height isn’t a problem.” We both laughed.

Our hour-long coffee date flew by, and under different circumstances I would have loved to continue the conversation. She was strong, funny, direct, but she seemed OK with missing out on what she really wants from a relationship and settling for something mediocre in her romantic life. I left the date thinking I might better understand her on our next date.

Date #2: “Shannon”

“Shannon” read my profile and reached out to me to begin a dialogue. When we connected, she was upfront that she wasn’t yet clear on her limits—so if I was looking for sex today, I needed to move on. I told her I wasn’t clear either, and that coffee sounded good, hoping we could share a bit of time to see how we both felt.

Shannon was interesting: 35, dirty blonde hair, smart, funny, full of life, well-read and educated. She had made the decision to raise her two kids as a stay-at-home mom. She and her husband met in college and had been together ever since, but his attentiveness waned after the first couple of years. I asked why she stayed. Her answer: “Because I love him.”

I felt strangely comfortable with her, so I shared that I hadn’t had an affair yet, and that I’m new to the site and not clear on what to do—or when. She empathized, remembering when she was new to Ashley Madison. She’d had two affairs in the past, but they were strictly for sex, and it left her feeling empty. “Sex is great, but I’m looking for some time together, too. Not dating, but just something new. My husband is a great guy, but he talks to me like I’m stupid half of the time. And I have kids; I don’t want to leave.” 

At the end of our date, I keep things cool, and she asks if we can get together again. I tell her that I’d love to (knowing I can’t and won’t), and I ask her to reach me back on Ashley Madison. She’s sent me three messages since, and I answered the last one telling her that I realized after we parted that I couldn’t cheat on my wife—it's just not how I’m made. She responded, telling me she understood and wished me well.

Date #3: “Lisa”

I found “Lisa” by searching through the profiles. She was an attractive brunette, 5’4″, 39, 130lbs., two kids, residing in the Bay Area. After reading her profile (something I’ve been told many men don’t do with online dating sites), I sent her an inbox message telling her that I really liked her snarky attitude, her bold statements, and her general approach to life (which I had read about in her writing). 

Her profile stated that she wasn’t sure what she wanted from being a member of Ashley Madison, but she was clear that she wanted to chat with me.

We took the chat off the site to Yahoo! Messenger, and within seconds it was clear that she wasn’t after cybersex, she was trying to feel me out—no overtly intrusive questions, just getting to know me a bit. We talked about books, sex, great places to travel, music, movies and more sex.

After about 40 minutes of banter, I went in for the kill: “Want to grab a bite to eat this week?” I wrote, asking her to lunch. My convincer: “It’s just lunch. 60 minutes. If there’s no connection, no harm, no foul. And I know a great place in The City. Come join me. ;)” I typed, dripping with confidence. She agreed.

We met the next day at Albona Restaurant in San Francisco’s North Beach restaurant district. It was crowded, but she recognized me instantly from my profile picture, and I had already secured a table. We exchanged pleasantries, ordered a mid-day cocktail (I think I needed one), and began talking—me sprinkling in my interview questions throughout normal conversation. Over the next hour I played the part of the guy who was married but just couldn’t get into the humdrum of married life. I needed something. She quickly agreed with me and then spouted answers as I took mental notes.

I asked her why, with all the choices available to her, she had answered my email. Her answer: because of how I phrased things on my profile. Aside from the raw passion I had exhibited, she said I showed “thoughtfulness, intelligence, and a confidence” that came through in my writing—and I didn’t send her a picture of my penis.

At 39, with two young kids, she lamented that her marriage had grown cold, and her husband complacent. Her relationship was good in many ways—financially stable, secure, friendly—but it lacked... She stopped. I probed, “Passion?” and she almost leaped off her seat in agreement. She longed for spontaneity, the freshness that accompanies new relationships, and the effort that her husband had put in 10 years prior.

Midway through the meal, I started flirting with her. The challenge: I couldn’t get my wife out of my head. 

But as I continued, I found myself returning to the guy I was years before: focused on seduction, listening for clues to her wants and needs. We were now done with lunch, and I turned my attention to how far I could take her. As it turns out, she was the one who gave me the in by asking, “What do you find the most attractive about me?”

This question is a pick-up artist’s dream for a number of reasons. First, it speaks to her not having been complimented often enough, as she was fishing, apparently insecure and looking for validation. It also shows that she wants to know where my head is at; what do I see first when I look at a woman, and how does that relate to her? And lastly, it’s an inviting question, in that she wouldn’t have asked if she wasn’t interested in me. So, her simple question tipped the scales in my favor.

“You have a great walk,” I told her. She looked at me like I was crazy. “No, really,” I said. “You can tell a lot about a woman by the way she walks and her body language as a whole. Is she looking at the ground, unconfident, or is she standing tall, greeting the world? And, you have a swing when you walk,” I added playfully.

She was taken aback—as I knew she would be. A clever man might talk about a woman’s intelligence being a turn-on, but most men don’t usually talk about confidence in this fashion.

I moved the conversation from confidence-building to sex, and she followed along, clearly digging where I was guiding things. She was very interested in how I saw her, hungry for the compliments and clearly longing for the passion I started putting out. She reversed the question on herself and then told me what she liked about me, and the conversation tumbled into her passionate thoughts, how I was making her feel: relaxed, free, feminine.

At this point, I was in a dicey situation. I didn’t want to sleep with her, but the challenge of having her commit to giving herself over was intoxicating. So I kept pushing the limits and pouring it on, all the while hoping that my wife would understand the true motivations for my actions.

Fifteen minutes later—an hour-and-a-half after we arrived at the restaurant—I made The Ask: Was she interested in heading down the street to a nice hotel and experiencing what I have been describing? I told her I haven’t prepared for this but connections like this are rare and that I’m having a hard time controlling myself. I didn’t want to be so forward, but...and I stopped talking, letting my look fall to the floor. This gave her the illusion of being in control of the situation with a choice. A short pause and a coy smile from her told me instantly that she is absolutely hooked, and mine for the taking.

She agreed to go to the hotel with a whisper, and leaned across the table to kiss me to seal the deal.

And I froze. My body language changed instantly, and I sat back from the table and put my hand up to stop her advance.

“I can’t.”

“What?” she laughed.

“No, really. I can’t do this.”

“What are you talking about?” she asked, with genuine confusion. With a sigh—and for the first time realizing that I didn’t have an exit from this situation—I explained: “I’m working on a research project on adultery. This is a part of it. I’m sorry, but I can’t cheat on my wife.

I paused and she stared at me in disbelief. I had effectively brought her to the apex of her wanting, and now I was pulling the rug out from under her.

“So, this was all bullshit?” she asked through her teeth, not wanting to cause a scene in the restaurant. I sat motionless, unsure of what to do when she made the decision for me. With a look that would level an army, she seethed out, “Fuck you, Cameron,” and threw what was left of her martini at me. She turned and stormed out of the restaurant.

It wasn’t her fault. I’d be a liar if I said I wasn’t tempted—but my wife, my honor, my word and my humanity are not worth it, no matter how attractive she might have been. After patting myself dry amidst slack-jawed looks from other diners, I left the restaurant and headed home. I was emotionally spent.

The Fight

As I pulled into my little suburb-of-a-town, I arrived at a local coffee shop down the street from my house, and I called my wife to see if she would join me. She agreed, but when she arrived I knew something was wrong. My thoughts were confirmed when I greeted her. With a smile on my face and my arms out to embrace her, I was greeted with, “Don’t even touch me, I can smell you from here. You smell like liquor and whores.”

This was not what I planned on, and this isn’t the way our open and honest relationship normally runs. She sat away from me, her arms folded in front of her, sipping her coffee and barely looking at me. I told her the story of what happened: the restaurant, the lunch, the flirting, the advance from Lisa, the cocktail. Her anger intensified.

“That’s bullshit, Charles. No one throws a drink on someone for nothing. What did you do? Just tell me. What did you do?”

For much of the afternoon, she fought with me. Given what my investigation was trying to uncover, and in light of my recent actions—even though they were “allowed” actions based on what we had discussed—I felt I had nothing to stand on. I tried to explain that I didn’t do anything, but she wasn’t buying it.

After three hours of not speaking to me, it became clear what was really bothering her when she told me emphatically: “You know, Charles, it’s amazing. I don’t care about your ‘date.’ And for all I care, you could have slept with her. But tell me this: When was the last time you took time out of your day and took me to lunch for no reason?”

A Revelation

Her statement to me was an eye-opener, and in polling 250+ women in the days that followed, I reached an important understanding. When an adulterous man is found out, there are many, many women that can get past the sex act itself.

But the real problem is where his effort has been going. As his wife sits idle, being supportive, holding down her half of the relationship, house and kids, a cheating man will put boat loads of effort into seducing the other woman: four-star restaurants and hotels, gifts, laughter, spontaneity, passion, sex.

From there, it’s a sad realization for his wife that translates to “I’m not worth the effort.” This is a fatal blow to her self-esteem and self-worth and terminal to the relationship. My wife and I got past it, but I had to relent to the fact that I hadn’t done those things for her recently. It wasn’t purposeful, but it was a mirror into my own accidental complacently (and I’m supposed to be an expert). It’s not that I take her for granted. But in acting like a cheater, I had fallen into my own trap. Accidentally? Perhaps, but does it matter? Isn’t the end result the same?

With all my experience and expertise, I keep learning.

Reflection

Contemplating all of my experiences with the women of Ashley Madison—chat sessions and in-person dates—several things became painfully clear. First, there isn’t one “type” of woman looking to cheat online. Some were looking to have sex, period. Others were looking to subsidize their current relationship with a human connection—and if it led to sex, even better.

But all were clear that they were not leaving their current relationship. These weren’t monkeys getting a grip on the next branch before letting go of the first. They just wanted to feel what they used to feel from the man in their life.

The most common complaint was a lack of passion and effort by the man in their current relationship. It makes sense. When a man begins dating a woman, he puts in tons of effort; he woos her. Once she’s “his,” he stops putting in that effort, but she still longs for it. She wants to be desired, seduced, and connected with on a regular basis. So many men seem to be missing the boat. They start strong, having a decent sense of how to capture a woman at the beginning, but upon entering a relationship they are unprepared for the long haul and investment a successful relationship demands past the dating phase. The situation starts to reek of complacency and satisfaction in mediocrity.

Should the women of Ashley Madison leave their current relationships before starting a new one? Yes, but the sad truth is that these women weren’t looking to start a new relationship. I got the distinct impression that they were filling their needs outside their relationships until such time that he noticed he was disconnected, it became unbearable, or it ended on its own. And until then, they were willing to settle for a half-marriage with a side of passion.

I still feel that cheating is the wrong thing to do, but this is the grey area I didn’t see before.

To the men thinking of getting married: being married isn’t like dating. Marriage doesn’t take “work” per se, but it does require concerted effort and investment in each other, and in you. If you aren’t into it, don’t do it, as you will be setting yourself up for failure—perhaps finding your wife on Ashley Madison. Or worse, out with a guy like I used to be, enjoying passion because you stopped bringing it.

Men in established relationships and marriage need to remember that women are women first and foremost—and wives and mothers second. If a man stops bringing passion and effort to his relationship and stops treating her as a desired woman, he shouldn’t be surprised when she feels forced to fill her needs elsewhere.

Charles J. Orlando is a relationship expert, bestselling author, and television and radio personality best known as the author of the acclaimed relationship book series The Problem with Women is Men. This piece was originally featured on Your Tango and republished with permission.

Photo via Jen BFO-CFN/Flickr (CC BY 2.0)

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