Sex & Relationships

What Happened When I Had Sex With Married Women I Met on a Website for Cheaters

"Life is short. Have an affair" is the motto of They have a point, don't they?

This article was originally published on

Experiment: To attempt to have affairs with married women via (Hey, back off -- they're clearly not getting the good stuff at home!)

Hypothesis: There are married women out there; they want me; I want them, and Ashley Madison will bring us together for illicit amoral roistering.


• Sense of guilt, shelved

• Loyalty to my fellow men, abandoned

• Ashley Madison account

• Wedded women

Background and a disclaimer: by nature I'm a one-woman man. Yes, right now I'm actually in an open relationship, but whenever I've been in something serious and monogamous, I didn't have any problems staying true. That said, I'm not a hardliner about other people cheating, especially if the cheater in question isn't getting any loving from their partner but can't leave him or her for economic reasons or because of the kids or for a number of other legitimate factors. Under those circumstances, I feel that the under-attentive spouse might well be getting what he or she deserves.

What I often wonder about, however, is why someone who wants an actual relationship starts things off with a married person. Aren't relationships hard enough without adding that complication to things? And how comforting can it be that your new friend is willing to run around on his or her spouse, lying all the while? To me, if you're going to be with a married person, it should just be light and playful, an adventurous physical thing, not something you're taking seriously.

And because I'm in an open relationship with a woman who actually lives with her other boyfriend (who knows all about me -- long story), seeing a married person would be pretty much the ideal arrangement. I'm extremely happy with my girlfriend and not going anywhere, I just need to keep things symbolically even by stepping out on the side while she's with boyfriend #1. And I know I'm not going to be able to provide anyone else a whole lot of emotional engagement, so I want their expectations low.

Single women often tell me they understand where I'm coming from (your basic emotionally unavailable asshole, right?), but my experience is that it can be hard to keep things sufficiently un-serious. With a married woman, there might be a much better chance, so Ashley Madison, here I come!

Method: For those of you who don't already know, is a personals website for married people or those who want to get with married people. Their motto -- "Life is short. Have an affair" -- is perhaps overly glib, but, again, if you're suffering through a loveless, sexless marriage and can't get out of it, I think I have to agree. Isn't everyone entitled to a little affection?

Compared to the interminable eHarmony profile process, filling out my Ashley Madison page felt like going through the EZ Pass lane. Actually, it felt like trying to pick someone up in the EZ Pass lane, since you don't get to reveal a whole hell of a lot about yourself or find out much about them. You pretty much only get to put up photos (which, if you're married, you might well be discouraged to do), give your vitals (which everyone seems to lie about), fill in boxes for what kind of interaction you're after (there were far too many people listing just "cyber chat"), as well as the kinds of fooling around you like (there's "light, kinky fun" but no "heavy, Rick James enslavement," sadly) and some activities that you'd enjoy doing (fine dining, sure, but sailing? How much time will we have?). Granted, they let you add a line at the end for each section, but it's still pretty superficial. (Oh, but wait, I'm looking for superficial encounters -- I guess that's okay!)

I filled out my profile, rounding my height up an inch to six feet even (I figured anyone who puts 5'11" is likely to look like Danny DeVito). I was honest about my weight and age (north of thirty-five but south of 175). I said I was looking for "anything goes" (anything?), and listed myself as single, as there was no box for the rather particular nature of my romantic life. (Though I'm surprised they didn't have an "It's complicated" box for people going through divorce, engaged but wondering, etc. Here of all places I thought they'd be sensitive to the range of situations.)

I clicked enter, took my moral temperature (turpitude), and looked myself in the mirror. Was this the face of a home-wrecker?

Observations: Readers, I confess, my first pass with Ashley Madison was pretty much a failure. I wrote to eight or ten women who had attractive photographs up, got a few responses but ultimately no dates, suspected that the young one who wrote me with the revealing "Private Showcase" was in fact a little too good to be true, and called it a week. The moral fabric of America: safe for the time being.

Then I made two important changes: I switched my status to "attached male seeking females" (I like how it's plural), and I started to contact women without pictures. If you're a man, it's always a good idea on personals sites to be the one willing to give the benefit of the doubt, but especially so here, where simple self-preservation -- not homeliness -- might keep someone from posting their mug.

Ah, how things can change. Now my inbox started to hang a little heavier. There was still a lot of sifting, rejection and flaking (incredible amounts of flaking, but that's the nature of internet dating), and one especially direct offer: "Hi. I am leaving the city in two days and would like to have some stress-free fun time with a nice guy. Let me know if you are interested." Tragically, I didn't see the note till a day had passed, and by then the job was filled.

Ultimately, though, I did meet up with four women, two whom I'd contacted and two who contacted me. Each was in her thirties or had just turned forty; there was a slender fashionista who looked like a cross between Gina Gershon and the daughter in The Incredibles; an affable giantess who looked like a larger and older Jennifer Capriati; a bright-eyed, full-bodied, mid-thirties version of Loretta Lynn; and a frisky, confident, Russian-born not-quite Michelle Pfeiffer. All of them had sent me photos before we met, and each was more attractive in person. As I'm far from photogenic, I was hoping I was as well.

The dynamics were quite varied. "Michelle" had teenaged kids, lived upstate but traveled for work, and wanted a longterm lover in the city. We met for a drink in a bar near Penn Station (before her train home), and she told me that while her husband was the greatest man in the world, he just was never very physical, and she married him too young to realize what a problem that was. She was super-smart and accomplished, and it was fun -- and even a little daunting -- being on a blind date with someone so self-realized. At the end we had a passionate make-out in the bar, but she wanted someone who would be completely devoted to her -- an affair, yes, but one of the heart. The fact that I was happy in my relationship meant she wouldn't be my #1. I respected that: she didn't want anyone to leave his wife for her, but she still wanted to be loved. That made sense to me.

Loretta, meanwhile, had a husband who was always on tour, and she was planning on leaving him when he finally finished the gig and wouldn't be devastated. We spent a few afternoons together, first sitting on a bench in Central Park, talking about music and books and the fact that she, too, hadn't foreseen how early marital troubles would continue to grow. She and her husband had dated briefly in their early twenties before he had to move away; she kept a candle in the window, and a decade later, they got together again, but her idea of him was still the idealization from their first time around. Reality, of course, proved to be another thing. For our second date, I invited her over, and we spent the afternoon lounging on my bed. But based on the ratio of talking to smooching, I suspected she was looking for more than just a sustained fling. I felt I had to nip it in the bud.

Jennifer was extremely game; we met for an afternoon glass of wine, took a walk around the block, and then went up to my place. From then on, she'd meet me at my apartment with the enthusiasm of a woman let out of prison. She too was in the process of leaving her husband, who had cheated on her (she agreed that they'd both grown apart), and we'd share a dozen playful emails a day. She called herself WWW (wet wild woman) and, with her boundless energy and appetite, would have made a perfect second girlfriend. But knowing I can't have serious feelings for more than one person at a time obliged me to end things, which sucked for both of us. Still, I know she's going to make someone very happy.

Gina, however, was the ideal mistress. We met for sangria, again in the afternoon to keep things either innocent or like an affair -- in any case not like a date. We drank quite a lot; I think we each were enduring the other's stories more than enjoying them, biding our time till we could touch. She wanted to leave her husband too, but neither of them was working, and they couldn't afford to move out. He slept on the couch, and they tried to avoid each other during the day. (I proposed starting a website for people in her condition so they could swap spouses.) She said she had met up with a lot of guys through Ashley Madison, but that I was going to be her last. I had to go back to work (sloshed) after the first time, so the second she came straight over. From then on, neither of us was too worried about conversation (she surveyed my home library and concluded we had no overlap), but we did laugh and smile and have genuine affection. She'd come in; I'd hand her a drink that she wouldn't have time to sip, and we'd be horizontal. An hour and a half later, she'd fix her hair, complain about her scraped face, and dress to go home. It might sound mercenary, but it was actually quite warm. Maybe oxytocin and whatever the male version is just hormonally made us feel close, or maybe sex with a splash of dialogue can create real intimacy, but I genuinely believe there was closeness. We didn't look or sound like we'd be a match, and it's hard to imagine that I could have met her in regular, day-to-day circles. But that just goes to show you that the world is much bigger than we tend to realize, and has many more people who can move us.

Conclusion: Ashley Madison works. Like most -- if not all -- internet dating sites, it's probably much easier if you're a woman, and it helps if you're not too picky. But there are definitely a lot of people out there looking for affairs. And, yes, some of the women clearly want something more serious, but others are simply looking to get the one thing that's missing from their relationship at home. As one woman told me, "I'd never leave my husband; I love him to death. We just stopped having sex three years ago, and I'm not ready to never have sex again."

This piece is part of a series called "I Did It for Science", published on Other articles in the series include:

I Did It For Science: Topless in the Park

I Did It For Science: Boob Power