The First 30 Days on Ashley Madison: A Male Perspective

Without question, the boys have it rough

A man’s profile picture on an adultery dating site.
Charles’ photo sort of looked like this in terms of theme and pose, but he was looking at the camera (Photo by Tyler Nix on Unsplash)

Last week I received an exciting offer in my electronic mailbag. It was an invitation from a man to interview him. He was just starting on Ashley Madison and had been on the site for a month. For the sake of the article, let’s call him Charles.

Here’s what Charles sent:

If you’re ever looking for story ideas, you can always interview me on my first 30 days on Ashley Madison for a male perspective. A soul-crushing experience, where no good deed goes unpunished. As a self-proclaimed high valued man, I get tossed out with the baby and the bathwater. As a feminist, I find AM a fascinating platform because it’s the only place I’ve ever seen women really in chargeWomen set the rules, women set the tone, and I wouldn’t have it any other way. If I don’t hear from you, that’s cool. I know you’re busy.

Well, first off, Charles, this girl is never too busy for a fan! But I am lazy and always looking for writers, so I asked him if he wanted to write his own story. It is still better coming from the source, but I offered to send him some interview questions as well, although, at the time, I had no idea what they might be.

Charles replied, I much prefer if you write it. Otherwise, it will just turn into a rant, full of mansplaining, and would lack perspective. Also, the written language isn’t exactly my strong suit, but I am passionate about this stuff and will probably write something in the future as my journey unfolds. But the effort required is quite significant these days, and I’m looking for the path of least resistance [aren’t we all Charles, aren’t we all]. So yes, send me your interview questions [damn].

I know my experience on Ashley Madison is very typical, but I don’t give up easily [good].

This is a bit of a shot in the dark for me, so if we don’t end up with anything, that’s totally cool. Definitely don’t want to divert your resources away from articles that may be more popular. But I do appreciate your willingness.

Divert my resources away? Not at all! My fans are my best resource because, without people like Charles, I’d have no one to write for.

I prepared for my interview by Googling some good interview questions. Not surprisingly, there were many questions a spouse could ask a suspected or recovering cheater, but not many for cheaters themselves, so I improvised a list and sent it to Charles. My first thought was to get to know him and his thoughts, ideas and experience with cheating.

My questions and his lightly edited answers are below.

What is your definition of cheating?

I must admit I have a pretty low bar here. Passionately kissing someone or engaging in sustained emotional and sexual correspondence with someone you’re attracted to without express permission from your partner.

That seems normal enough. I would likely add being on a dating site would be an issue as well.

Why do you think that people cheat?

I think we’re wired this way. Falling in love is such a powerful experience; how could we ever expect just to do it once and then not do it for a long time. Even with the full understanding of the fallout, love is a very painful experience, but it doesn’t stop us.

I think that love comes in different forms, but that hot burning love is the one that’s the most powerful and addicting, whereas longer-term love requires more of a slow-burning love.

What did you think of people who cheat in their relationships before you considered cheating?

That they’re selfish and lack self-control.

I get it. We all have a little high horse inside us. The other thing is, when you aren’t thinking about cheating or having an affair, it’s easier to be judgemental about those who are. After all, we’d never do that, right?

Why do you think you want to cheat, or why have you cheated?

Number one, I’m selfish; number two, I love sex and affection.

Well, there’s consistency there, I guess. Loving sex is a given, but the last one is interesting. Affection. This comes up time and again, and it is interesting to hear it from a man. I’ve written about skin hunger before, which is the lack of physical touch. It affects both women and men, but it’s nice to hear a man admit he loves affection, to the point he is thinking of cheating to get it.

What do you think of people who cheat in their relationships now?

I really think it’s more of a systemic problem. If it were more socially acceptable to cheat, it would be more socially acceptable to have relationships where this permission was granted. It’s society’s fault and not the individual’s. It’s a rigged game.

I think Charles is right. It is a bit of a rigged game of sorts. The idea of couples separating off for life seems to have been ingrained in us, but is it a reasonable expectation?

Why do you think your view on cheating has changed if it has?

I’m definitely more sympathetic. We’re just humans ruled by emotions. What would you do for that next hit of oxytocin? Do you remember what new relationship energy (NRE) feels like?.

Oxytocin is called the love drug. It is released when we have sex and intimacy, and it’s what makes affectionate hugs feel good. NRE is something cheaters refer to often, and many chase the oxytocin high. What would you do for your next hit? Some people chase new relationships to keep the feeling alive.

Have you ever been cheated on by somebody?

No, Not that I’m aware of.

I don’t know why I asked this question, but it seemed to me this might be the sort of experience a cheater should have first-hand before deciding to step out. I’ve never been cheated on either that I know of, and I prefer it that way. Would I have a different view if I had been? I’m not sure, but I understand how going without sex and intimacy for nine years felt…

Have you ever cheated on someone?

Based on my own definition of cheating, yes. But I’ve never gone all the way, but that’s more of an opportunity problem than a motivation problem.

This speaks to the once a cheater always a cheater discussion. I think having cheated once, it makes cheating easier to rationalize and do. I also think cheating has a lot to do with opportunity. It’s the age-old question if cheaters fuck in a forest and no one is around to see them, did they fuck?

Have you ever been caught cheating?

No, however, I have had a couple of close calls. My wife found a Tinder app on my phone. Luckily the profile was deactivated that time, so when she opened the app, nothing was seen.

It’s these little incidents that become lessons learned. Your OPSEC as a cheater or potential cheater can never be too high.

If you had a chance to cheat now, would you take it?

Yes, this doesn’t justify it in any way, but I’ve always had an extremely high sex drive. I believe it has to do with some very positive sexual experiences I had while I was quite young. Also, I believe genetics plays a role. Also, my wife suffers from depression and takes Zoloft (antidepressant), and it absolutely kills her sex drive. For her, sex is a chore or an obligation. She enjoys walking the dog a 100 times more than having sex. Before the depression, she was my partner in crime with an insatiable sex drive.

I’ve tried to suggest we do some kind of therapy, and I spent five years trying to make her interested in dating, but nothing has worked. I think the worst part is she thinks she’s meeting me halfway, but she is not. I simply don’t have the courage to tell her otherwise.

I understand this, and I don’t even have a high sex drive. I would say I have an average sex drive, but unlike Charles, I get zero, so we are in the same situation. People might ask why we don’t talk to our spouses about it, but it’s courage. How do you tell a depressed person they aren’t holding up their end of the marriage when they think they are, without hurting them? I don’t know how many times I’ve read “talk to them” from well-meaning people who have no idea what a long-term illness looks like.

The End of Part One

Through our emails I think I got a good sense of Charles. Very quickly into it, I started feel like Charles needed a little help, so I made him a promise.

I told him I would stay with him, and work with him, until he gets his first date.

Why? AM can be brutal for men as he quickly learned, because, as he says, the women are in charge. Because of that I wanted to help him. So what does this help look like so far?

My first step was to have a look at his AM profile and offer him some pointers. I asked him to send it to me so I could see what the ladies landing on his profile would see. I also asked him to send me the last three messages he sent and to also forward his favorite profile picture. I wanted to analyze how he was selling himself in these three different ways.

I also told him to build a lady’s basic profile and to start checking out the competition.

I’ve sent him what I think of his profile write-up and suggested changes. I looked at his pictures and asked a few questions. My next article will discuss what I recommended Charles do and what he thought about that. I still owe him an assessment of his questions, but I still have an idea percolating in my head about this.

Stay tuned for our next visit with Charles so we can see where he’s at.


Following or initial interview, here’s how my analysis of Charles’ dating profile went –Analyzing Charles’ Ashley Madison Profile
Some men don’t realize how important their adulterous profile ismedium.com


Here’s where I shredded some Ashley Madison profiles and messages for shits and giggles 😉Can All the Gentlemen of Ashley Madison Be This Stupid?
Testing the pathetic waters for sport and adventuremedium.com


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© Teresa J Conway, 2021

By Teresa J Conway on .

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Exported from Medium on April 8, 2021.

Author of How to Cheat: Field Notes from an Adulteress, several short stories, I'm active on Medium @teresajconway where I sometimes share my blog posts, and I'm a fair-weather tweeter @tjconway69.

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