Why Women Cheat: A Married Man Goes Undercover On Ashley Madison

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why women cheat, ashley madison
A married relationship expert joins Ashley Madison and learns a valuable love lesson.

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 (who's 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 (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 (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, and 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. 

But 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 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 ask 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, 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 "passion and romance" when they dated, but had 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 ..." and 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 since, but his attentiveness waned after the first couple of years. I asked why she stayed. Her answer: "Because I love him."

I feel strangely comfortable, 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." We talk more and it's clear she wants to laugh, to live, to love. I wonder why she stays with her husband.

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/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… just not how I'm made. She responded, telling me she understood and wished me well.  Keep reading...

Article contributed by

Charles J. Orlando

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