I Went Undercover On Ashley Madison To Find Out Why Women Cheat
How I learned to be a better husband by pretending to have an affair.
TONL | Canva "Honey, I have to join Ashley Madison." So began the pitch I gave my wife to let me join the married-people-looking-for-affairs online dating site, Ashley Madison. It would be part of my research on why women cheat, why infidelity is increasing, and what can be done to possibly affair-proof a marriage.
I proposed that my wife let me "cheat" on her for a few weeks on Ashley Madison.
I asked that she allow me to talk to and attempt to seduce as many women as possible at that time 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-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, 1.5 million+ readers and fans following my relationship advice on Facebook — I was a chronic womanizer; 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 reek of negativity on vulnerable women to break them down and manipulate them into being intimate. No, I was far more despicable 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 being intimate with me was all 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 situation. "That was 15 ... no, 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. Mess. Up."
Vlada Karpovich / Pexels
According to The Journal of Couple and Relationship Therapy, 45-55% of married women and 50-60% of married men will have an extramarital affair at some point in their marriage.
When you consider these statistics are nearly double what they were a short 10 years prior, clearly this is beyond an issue; cheating is now commonplace. But this information is 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. 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 already failed marriage.
But is it so black and white, with no gray 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 advent of the Internet has made having an illicit affair easier than ever before, a mere mouse-click for anyone with a credit card. If you're looking for a quick fix, there are apps for that. But intimacy-only semi-anonymous hookups weren't where my investigation was headed, as women looking to merely be intimate can meet a man anywhere — nightclubs, coffee shops, Facebook, wherever.
Alexander Mass / Pexels
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 intimate relations sans spouse. The undisputed leader for cheating is Ashley Madison, the website originally known for its cheeky motto — "Life is short. Have an affair" — only to be rebranded under the tagline "Find your moment" following a major hacking scandal in 2015.
At the time, Ashley Madison had been experiencing meteoric growth since its founding in 2002, with no slowing in sight, regardless of that big leak of its users' confidential information in 2015, which left many a cheater exposed.
And while founder and former CEO Noel Biderman says he doesn't condone having an affair, he seems perfectly comfortable with others doing their adultery thing. Works for some — and now, it was my turn to get my own (feigned) cheat on.
I filled out my nickname and relevant info, plopped down my credit card number (the charge was discretely billed as "AMDB" to my credit card statement), and then all I needed to do was ... wait a second. I was faced with the eternal online seduction dilemma: now what? What would make women want me online? What would women want to see on my profile?
Reports following the aftermath of the hacking scandal revealed that only 15% of all Ashley Madison accounts belonged to real women, though at the time they claimed statistics their community was comprised of 70 percent men and 30 percent women. Either way, women had the upper hand when it came to 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 named "Shelly" and began checking out the guys' profiles as well.
Most of the men's profiles highlighted attempts at humor, asking straight-out for intimacy, to ... uh ... romance, i.e., "I like walks on the beach." Really? Walks on the beach? Come on, now ... no, you don't! I mean, we all like walking on the beach, but that's not why you're on the site. And besides, the 1970s called, and they want their pick-up line back.
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, confident, and (hopefully) 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 …" "Cameron" was closer to the middle — "Too many men get comfortable, even complacent, and forget that foreplay starts outside the bedroom."
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.
Andrea Piacquadio / Pexels
Given the demographical split on the site, I was prepared to search and wait for several days for interest or responses, but to my surprise, Cameron's profile had 20 messages in its inbox on his first night.
I responded to a few messages, and before I knew it, I was invited to a chat session with "HotCat" (profile name changed to ensure her anonymity). HotCat wanted to know all kinds of things, including 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).
HotCat wasn't the only one. I discovered that to satisfy their deep longing for passion with minimal risk, many women signed up for Ashley Madison seeking intimacy via chat. Over the next several days, I had chat sessions of varying lengths with 33 different women (hmm ... it is online ... I wonder if they were all 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. I hope I didn't disappoint them and that virtual cigarettes were ablaze in the bedroom of my cyber 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 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 explicit material these ladies had written, as well as what I wrote in response, and we both said aloud what we have known for a long time: When it comes to being physical, women will get into the real details so much more so than most men. And with the inherent anonymity of chat, those inhibitions only grow exponentially.
But Ashley Madison had more in store for me than just chat sessions:
Real-life Ashley Madison 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 and 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, intimacy — 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 all passion and romance when they dated, but had become all work and no play since they married. 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 ..." and we then dropped the subject at her request. She was extremely intelligent and witty — and she was just as clear that intimacy 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, and direct, but she seemed okay with missing out on what she wanted 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.
Katerina Holmes / Pexels
Real-life Ashley Madison 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 regarding intimacy. 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, with dirty blonde hair, smart, funny, full of life, well-read, and educated. She had decided to raise her two kids as a stay-at-home mom. She and her husband met in college and had been together 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, so I shared that I hadn't had an affair yet and that I was 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 intimacy, and it left her feeling empty.
"Being intimate 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."
We talked more and it was clear she wanted to laugh, to live, and to love. I do wonder why she really stays with her husband. At the end of our date, I kept things cool and she asked if we could get together again. I tell her that I'd love to (knowing I can't/won't), and I ask her to reach out to me back on Ashley Madison.
She sent me three messages following our date, and I answered the last one telling her that I'd realized after we parted that I couldn't cheat on my wife; that it's just not how I'm made. She responded, telling me she understood and wished me well.
Real-life Ashley Madison date #3: "Lisa"
I found "Lisa" by searching through the profiles. She was an attractive brunette, 5'4", 39, 130 lbs, with 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 a message telling her that I 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 a hookup; she was trying to feel me out. No overtly intrusive questions, just getting to know me a bit.
We talked about books, intimacy, great places to travel, music, intimacy, movies, intimacy. 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 was 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 — that and I didn't send her a picture of my private parts.
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 ... and 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 was that 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.
When we were done with lunch, I turned my attention to see 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 several reasons.
Firstly, it speaks to her not having been complimented often enough, as she was fishing, apparently insecure and looking for validation. Secondly, it shows that she wanted to know where my head was at; what I see first when I look at a woman, and how that relates to her. And thirdly, 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 intimacy, and she followed along, clearly digging where I was guiding things. She was very interested in how I saw her, hungry for compliments and 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 and 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 hadn't prepared for this, but that connections like this are rare, and that I was 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.
A short pause and a coy smile from her told me instantly that she was 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 cheating. 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 a lie" she asked through her teeth, not wanting to cause a scene in the restaurant. I sat motionless, unsure of what to do when she decided for me. With a look that would level an army, she seethed out, "Screw you, Cameron," and threw what was left of her martini at me. She turned and stormed out of the restaurant.
My heart went out to her. 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 weren't 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.
As I pulled into my little suburb of a town, I arrived at a local coffee shop down the street from my house and 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 other women."
Whoa! 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 a lie, Charles. No one throws a drink at 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 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 to take me to lunch for no reason?"
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, many, many women can get past the physical act itself. 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, kids, etc., a cheating man will put boatloads of effort into seducing the other woman: four-star restaurants and hotels, gifts, laughter, spontaneity, passion, intimacy.
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 … and it wasn't purposeful, it was a mirror into my own accidental complacency (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 trap. Accidentally?
Perhaps, but does it matter? Isn't the result the same? With all my experience and expertise, I keep learning.
Diva Plavalaguna / Pexels
Contemplating all of my experiences with the women of Ashley Madison — chat sessions and in-person dates — several things became painfully clear, the main being that there isn't one "type" of woman looking to cheat online.
Some were looking to hook up, period. Others were looking to subsidize their current relationship with a human connection, and if it led to being intimate, 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 regularly.
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 she was disconnected, it became unbearable, or it ended on its own. 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 a gray 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 yourself.
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 her passion because you stopped bringing her yours.
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.
*All names have been changed to ensure each individual's privacy.
Charles J. Orlando is a relationship expert best known as the author of the acclaimed relationship book series, The Problem with Women… is Men.