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


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

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, sex, movies, 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 ... 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: 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. 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 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 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 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.

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 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."

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 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?"  Keep reading...

Article contributed by

Charles J. Orlando


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Email: advice@charlesjorlando.com

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