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The Single Men of Ashley Madison

I spent months on the notorious dating site talking to bachelors about why they’re so obsessed with married women

My journey into the underbelly of infidelity starts when a friend of mine — let’s call her “Kelly” — split from her husband. She decided after 20 years of being in “prison” that she needed to make up for lost time.

“So I’ve been on Ashley Madison,” she confesses to me one day over coffee.

“That place still exists?” I ask in return.

The last I’d heard about Ashley Madison, the controversial website that facilitates affairs — or as they adorably refer to it, “the premier destination for married dating” — was back in 2015 when it was hacked and the names and personal information of millions of subscribers were released online. The collateral damage from the security breach was messy and far-reaching. Identities were stolen. Jobs were lost. Families were destroyed. A pastor and father of two even killed himself after it was revealed that he was on the site.

But as modern life moves faster, our attention span grows shorter. 2015 feels like decades ago, and it appears all has been forgiven — or at the very least, forgotten.

“It’s a happening place,” Kelly insists. She tells me about “Hot Lawyer,” the man she decided to lose her “20-year virginity” to after she met him for coffee. “After our date, he walked me out and we kissed. I got butterflies for the first time in two decades. He pulled me into his Tesla and moved the car seats aside so we could make out.” She pauses. “Yes, I realize that’s hilarious.”

They decided to go to a hotel, which he paid for. “I was really nervous,” Kelly says, “but he held my hand in the elevator. I thought that was so sweet.” They “did it” and ended up hanging out and chatting, “like a slumber party.”

According to Paul Keable, Vice President of Communications for Ruby Corp., Ashley Madison’s parent company, “Ashley Madison has more than 54 million member accounts since we launched in 2002. Currently, we average 20,000 new member accounts a day, which is almost double what we had this time last year.” Ashley Madison recently analyzed their data to determine the top cheating cities in America based on new user sign-ups — L.A. (where I’m based) comes in at number one with a 47 percent increase of new accounts.

“You should check it out,” Kelly says. “When we were having our pillow talk in between sex sessions he mentioned his ‘ex-wife,’ and I told him I was actually separated, too.” Kelly laughs, “We were both lying about being married.”

“So Hot Lawyer was actually single?” I ask.

“There are a lot of single guys on there,” Kelly says. “And they’re hot and successful! Of the four men I’ve gone out with, all of them said they were married, but two of them weren’t. They all had nice cars, though.”

“Why are single men on Ashley Madison?” I respond.

I’ve lived to regret that question.

First Impressions: So Many Dicks

I’ve been on Ashley Madison for less than 48 hours, and I’ve already seen at least 100 unsolicited dick pics, definitely more dicks than I’ve ever seen in my lifetime. It’s so bad I have to put “LEAD WITH DICK PICS AND YOU WILL GET BLOCKED” in my Ashley Madison bio. According to an Ashley Madison survey, 73 percent of female users receive uninvited nudes. The epidemic is so rampant it prompted the site to launch a campaign that “urges men to call it quits with dick pics.” You know it’s bad if Ashley Madison is telling you to keep your dick in your pants.

But here I am, staring at a sea of mediocre penises in a virtual cock gallery. I’m more offended at how awful the pictures are; no one wants to see a small, poorly lit, flaccid penis dangling in a jungle of gnarly pubes.

Ashley Madison was one of the OG dating sites. Preceded only by Match.com, eHarmony and JDate, Ashley Madison was the first website to challenge traditional relationship norms. Although sites like Fetlife and SeekingArrangement are ubiquitous today, back in 2002 when it was launched with the (now retired) slogan, “Life is short. Have an affair,” Ashley Madison provoked outrage.

Now, it gets a shrug and an eye-roll. No one takes it seriously because it’s a punchline. The place that gets hacked, only to find it’s riddled with fembots, a host of “sex addicts” and Josh Duggar. It’s the ultimate sausage party.

As for me, I set my relationship status and filters to “single,” and yet, my mailbox is bombarded with men labeled as “attached” — not exactly what I’m after.

The married guys on Ashley Madison run the gamut. They range from men in open relationships, to men with “don’t ask, don’t tell” agreements, to men who are blatantly cheating and love the thrill of the affair, to sad men in loveless relationships. The latter seem to be the majority.

I’m pleasantly surprised at how handsome they are. I don’t know what I was expecting, but it wasn’t tall studs, which, looking back, makes sense. Of course these type of men are feeling restless in their marriage. In the real world, I’ve come across many hot alpha males who get hit on everywhere they go but nagged to death at home. That combination can kill a marriage — or bare minimum, all the affection and passion. Most of them also seem to be doing pretty well financially from what little I can gather. Plus, the very fact that men have to pay to be on Ashley Madison eliminates a lot of the unemployables. As one man explains to me, “We pay for the credits for the first message, but after that, there are no more credits charged. They sell membership packages. X amount of credits for X amount of dollars.” Depending on how much you want to spend, “it’s like 40 cents per convo.” (It’s free for women.)

“Are you real?” is always their first question.

Keable claims that “our community of like-minded people is made up of roughly 1 active female for every 1 active paid male.” But I find that hard to believe. Back in 2015, for example, Gizmodo journalist Annalee Newitz analyzed the source code and discovered what many Ashley Madison users already knew or suspected: The site was populated with pay-to-play fembots. According to every man I interact with, this hasn’t changed: “It’s all bots, and women looking for sugar daddies.”

I relay this information to Keable, but he holds firm, “I can say with absolute certainty, there are no bots on our platform. This has been confirmed by Ernst & Young. The numbers we provide are only real members.”

I’m also dubious of the 1:1 ratio because being a woman on Ashley Madison feels like being the last glass of water at the end of a marathon. The thirst levels can only be described as desperate. The attention isn’t just overwhelming, it’s depressing.

One guy in particular — screen name: 53542611, whose bio reads “unsatisfiedly married” — breaks my heart not only because spelling clearly isn’t his strong suit but because under, “What I’m looking for,” he lists, “Dinner, movies, chatting, kissing passionately for extended periods of time.”

His loneliness strikes a chord with me.

I was married at 23 years old. By the time I was 27, we’d already settled into that comfortable prison routine that marriage can start to feel like. I knew we needed to separate. Communication had stopped. Drinking had increased. I got chubby. He got lazy. Sex decreased. Resentments piled up, and soon, I heard the kiss of death in my voice: Contempt. We stopped building each other up and started knocking each other down, chipping away at one another’s spirit, little by little. I was having a hard time staying faithful. He was miserable. I ejected out of the marriage before we crashed and burned — or worse, dragged kids or property into our mess.

Which is to say, the married men of Ashley Madison aren’t here just for sex, although that’s the primary reason. They’re here to feel admired again. They’re here to find a woman who hasn’t slept with their snore for decades, washed their dirty briefs or heard them fart. They’re here to escape that tone of condescension that comes with familiarity and replace it with an hour’s worth of adoration. They’re here to feel revitalized.

As one man explains to me, “I’m married but zero sex life for a long time. We have two kids under five and that’s mostly why I stay in the marriage. The big missing piece is intimacy. The affection is almost nonexistent. It’s almost like for me if there was some affection I could deal better with no sex or little.”

According to a recent survey done by Ashley Madison, my experience on the site reflects this same pattern: “Sex is the number one reason why people choose to cheat (61 percent).” But “some want to expand the physical elements like exploring new desires (45 percent), while others are looking for emotional reassurance like affection (44 percent), friendship (42 percent) and the feeling of butterflies again (30 percent).”

These guys get a bad reputation as “cheaters,” and at first, I have a lot of compassion for the married men on the site. I firmly believe it takes two to cheat, even if one person assumes a passive role. I read hundreds of bios that said things like, “Tired of feeling like a roommate. Want to feel desired” and “Monogamy is monotony. Not sure what to expect here, but looking for the spice that has long since left.”

But after a week, what little faith I have left in a man’s ability to be faithful is slipping away. I need to take long breaks from the hundreds of degrading messages from guys screen-named RegenerateMe and lyketolaypype who write things like:

I’m visiting my mother who is being treated at the Mayo Clinic. I’d love to meet me a lady friend to lick it with at night after mom goes to bed… Yes, it is that type of late night situation that I’m looking for while her. I have a mind blowing tongue, and your first moustache ride is always on me.

And:

Some of my desires are, I like that I can have my way with you. With me being 6’5” tall, I can easily dominate.

But despite my inbox being flooded with married men promising me a world of orgasms, BDSM and analingus, the single men remain elusive. According to my search parameters, there are 220 single men seeking women within a 20-mile radius. I even message a few of them first and still get no response. I can see that some of them have “viewed me” but only silence follows.

So what’s the deal?

Why the cold shoulder?

While contemplating answers, I remember that Kelly had presented as married when she created her profile and that most of the men she ended up with were also presenting as married, despite being single. Maybe that’s the problem. This is a “married dating site” after all. So I change my relationship status from “single” to “attached female seeking male.”

And just like that, the floodgates open. Like a dog whistle, the singles come running into my inbox, eager to piss on another man’s tree.

Or wife.

The Fuckatype Archetypes

Since Ashley Madison is an unfiltered sub-culture, and since everyone assumes everyone else is breaking a moral boundary, there are no moral boundaries. It’s the Vegas of dating sites, and just like Vegas, single men seem to be having the most unadulterated (excuse the pun) fun.

They usually fall into one of three types:

  • The Recently Divorced
  • Commitmentphobes
  • Cuck-Makers/Desperate Housewives Hero

No matter their archetype, though, the single men of Ashley Madison aren’t looking for love or affection. They aren’t in sexless marriages with wives who emasculate them. They want to fuck and cuck.

That said, of all the men I interact with on Ashley Madison, the Recently Divorced are definitely the most respectful. Case in point, Troy, whose bio reads: “I am considerate, I open doors, and I am a good dad. I am also a very sexual person and I would like to have some fun and explore some fantasies. I am very talented in bed and I am a really good kisser. I absolutely love to show that off because I didn’t get much opportunity in my marriage.”

Guys like Troy mainly seem to be trying to avoid relationships and the shame of being spotted by mutual friends of their ex on Tinder and Bumble. There’s a level of discretion on Ashley Madison that isn’t available on apps you swipe through. You don’t have to show your pictures until you’ve vetted the other person. And you can remain anonymous for as long as you want (until it gets hacked again).

Plus, for men coming out of 20-year marriages into the fast-paced, soul-crushing world of swiping, Ashley Madison can function as a more controlled environment while they navigate their return to the dating market. As Troy tells me, “I’m looking for a woman who’s looking for passion and excitement and can get away once in awhile, some days, some nights. If you’re already separated or recently single, it would definitely make it easier for both of us. I divorced last year, and I’m definitely not looking to get into another marriage, which is why I’m testing it out here.”

I ask every man who identifies as “single” the same question: “What’s a handsome guy like you doing here and not somewhere like Tinder?” The most common response is, “I’m too busy for a relationship.” In other words, a lot of these guys are married to their jobs. But Nautiboi69 sums up the other main reason perfectly: “Ha. Girls on there are still looking for a relationship. I’d rather be with a girl in a relationship so I know she isn’t looking for something. Plus, this is exciting I think.”

I understand the thrill-seeking. I’ve been a man’s mistress, so I get it. The passion and heat that comes from organizing and anticipating the midday tryst is part of the foreplay; getting fingered on a hiking trail overlooking the ocean, at a halfway point between our homes, is the score.

But specifically seeking out unavailable women because you know they can’t fall in love with you, demand your time or really anything from you? That’s some next-level emotional unavailability.

Or: These guys have found the loophole in the system. Nautiboi69 is right when he says that women on Tinder are still “looking for a relationship.” Most women want a relationship, even if they say they don’t, and have to play some game (i.e., lie) to get it. Most men are looking for sex but can’t outright say that’s what they want and have to play some game (i.e., lie) to get it.

But not the single men of Ashley Madison.

Kelly thinks they’re gaming the system. “They’re geniuses!” she exclaims. “They’re getting free sex.” It reminds me of the famous Charlie Sheen quote, “I don’t pay a prostitute for sex. I pay them to leave.” But the single men of Ashley Madison don’t have to pay anyone (except Ashley Madison). They don’t have to feign interest on a Tinder date. They don’t have to spend money on drinks. Maybe they’ll spring for a hotel room, but because they’re single, they can just have you over to their place.

I decide to meet one such man for coffee. Full disclosure: He led with a dick pic, but his dick was nice, so I didn’t hold it against him. We have a pleasant enough conversation in which I lie to him the entire time. I tell him I’m in a dying marriage and bored with my husband, who’s the only man I’ve ever been with. When he asks me what I do for work, I respond that I help nonprofit organizations get their 501c3s.

Honestly, pretending to be an innocent, Midwestern girl who writes articles of incorporation and is married to her high school sweetheart is more intoxicating than anything I’ve experienced in a while. I sit differently, my posture more controlled. I speak differently, too, my voice sounding softer.

Nice Dick seems fine, but I’m worried I’ll tumble down a rabbit hole where I’m addicted to getting off on being undercover and he’s getting off on thinking I’m married. In fact, there’s enough chemistry that I probably would’ve gone home with him (because, of course, he lives right down the street from the coffee shop we meet at) if I were actually the person I’m pretending to be: a sex-craved married woman.

“I’ve been that sex-craved woman,” Kelly says. “And that’s exactly what I wanted to do and did. I met men in hotels. I had coffee and fucked them in their car. I had sex with micro-peens. I’d get annoyed when the men wanted to date. I felt like I was in heat.” Kelly was coming out of a marriage where she’d lost all interest in sleeping with her husband. “Not just having sex — fucking — you need to fuck, passionately and regularly, to keep that shit alive.”

Although I didn’t go home with Nice Dick, I left the hint that I might, and three months later, he still hits me up on Kik (the anonymous messaging app users quickly graduate to because Ashley Madison’s messaging sucks worse than Twitter).

He’s not alone in this regard. I cannot emphasize enough how thirsty all these guys get if they think there’s so much as a chance. They’re so hungry, needy and pathetic, I wonder how many of these interactions actually convert to passionate, no-strings-attached sex. When I press them to tell me how many horny housewives they’ve bedded, I get vague answers like “a couple” or “I’ve had a few.”

I interpret it as a dodge, bullshit or some variation therein.

On the Hunt to Cuck

After the Commitmentphobes, the Cuck-maker (and its close cousin, the Desperate Housewives Hero) is the next most common type of single man I run into on Ashley Madison. Part wannabe savior, part narcissist and part thrill-seeker, these guys want to hear all about how my husband is failing me as a lover and how they can be the man he isn’t. “I have a taste for women who know what they’re missing and I love filling that need — and their pussies with my huge cock,” writes TasteeDee33.

Smiley face. Wink. Puke.

“I’m just into the sexual intensity of married women and how you generally know what it is you’ve been craving and you take it,” JoeSchmow007 messages me. “So, what have you been craving?”

It gets to the point where I’m feeling bad for my imaginary husband because part of the foreplay for the Cuck-makers is nitpicking said imaginary husband’s inadequacies. SlickWilly1998 wants to know, “Did he cheat on you?” (Apparently a lot of the married women who are on the site are there after they find out about their husband’s infidelity.) “A gorgeous woman like you deserves to be worshipped like a goddess. Does your husband worship you?” SlickWilly1998 presses. “I bet he doesn’t.”

“Let me inside you before your husband gets home,” another man messages me.

Even if these Cuck-makers don’t initially express the desire to cuck my husband, about a third of the interactions end up with the man conveying some kind of desire to outperform my mate. “I came four times last week,” HornyTowed claims. “Can your husband still do that at 40?”

“During my 25-year career as a sex therapist, I’ve seen hundreds of single men who are turned on by having sex with someone else’s wife,” says sex therapist Kimberly Resnick Anderson. “It’s all about genetic fitness. Nature is chock-full of ‘Evolutionarily Stable Strategies.’ These strategies ensure perpetuation of the human species. ‘Sperm Wars’ (aka Sperm Competition) encompasses both literal physiological battles between sperm inside a woman’s reproductive tract to fertilize an egg, as well as figurative battles between multiple men who compete for the same woman’s attention.”

Anderson also shares this anecdote with me:

I treated a man who was single but was having an affair with a married woman. He’d show up at her house just before her husband was due to arrive home to ask her to give him oral sex and swallow his semen. Then he would leave as soon as she was finished. Before he left, he instructed her to greet her husband with a passionate, open-mouth kiss when he walked in the door.

He would then sit in his car until her husband got home and watch him go inside. Even though he had just ejaculated minutes prior, the thought of his semen being in her mouth while she kissed her husband was an incredible turn-on. He ejaculated in his car as he imagined it happening just 20 feet away inside their home.

When I asked my client what was so arousing about the scenario, he said that he felt powerful because he had humiliated her husband (by putting semen in his mouth without his knowledge or consent); and because she was willing do that that for him (with no regard for her husband). ‘Those are the best orgasms I ever have,’ he boasted. ‘I felt like I had cuckolded her husband and proved that I was the dominant one.’

According to Anderson, some men become so dependent on this idea that they cannot maintain an erection or ejaculate unless they’re having sex with someone else’s mate. “Their erotic script is steeped in themes of humiliation, aggression and a complete lack of intimacy,” Anderson explains. “These themes drive their behavior and are the motivating force in their conquests.”

Signing Off

“The idea of your husband slipping inside you after my cock was just throbbing inside of you. It’s hot.” By now, I’m used to messages like this from anonymous, faceless, ridiculous screen names like BahdeeWurshipur2000 after months of posing as a married woman on Ashley Madison.

Not to mention, I’ve come to an understanding. I’m able to somehow overlook the honky screen names, the bots, the scams, the working girls and focus on the actual married men in pursuit of the site’s grand promise. And if I’ve learned anything navigating the treacherous rapids of a place specifically created for “sin,” it’s that underneath all of the dirty talk, the deception, jealousy, competition and heartbreak, lies a deep need to connect with another human being and an animal instinct to procreate.

This desire for connection doesn’t always look the same, but when you peel away the layers of our psychology, our background, our pain, our hopes and dreams, our fantasies and our kinks and fetishes, the evolutionary drive to survive reigns supreme. It’s at work, even when we have no idea why we’re doing what we’re doing and despite what’s at stake — in this specific case, relationships, reputations and/or personal safety.

When I first came to Ashley Madison, I admit I had an attitude of judgment and (hypocritical) moral superiority. Over time, as I’ve gotten to know the men behind the masks, I’ve come to a place of compassion. There are douchebags there for sure, but the majority of the men seem sad, desperate and lonely. On Ashley Madison what looks like the worst of humanity is really humanity at its most honest, vulnerable and primal.

In fact, I have a new slogan for the website: Welcome to Being Human. It’s Messy.