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

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A married relationship expert joins Ashley Madison and learns a valuable love lesson.

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.

Article contributed by

Charles J. Orlando

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