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What I Learned as a Single Woman Dating Married Men Online

Everyone lies and many of the men are desperate creeps, but for single women it's an easy way to go on expensive dates without worrying about commitment.

Last week we posted an article by a married man who uses Ashley Madison to cheat. This is what it's like to use the notorious dating site as a single woman.

Last week, I went out with a nice guy. We met at a storied bar (think the Stork Club, if it still existed) and had a great time. He was charming, polite, and incredibly attentive. He graciously picked up the tab and asked if he could see me again soon. I said yes. He slipped me some cab fare, hailed me a taxi, and said goodnight.


Before you ask: Yes, I knew that he was married.

We met online, on Ashley Madison, a dating website for those who are married and looking to bag themselves an affair.

I'm a college-educated woman in my early 30s from a solid family (no daddy issues here). I'm also single. I get the occasional bout of loneliness, but I'm not lonely enough to get myself tied up with an actual boyfriend. I've got a career to build and don't have time to spend on someone else's needs/wants/feelings right now. Ashley Madison was an opportunity for me to meet people outside my immediate social circles, experience the best of the city (fine dining and drinks on someone else's dime), and best of all, I didn't have to put forth any commitment. These men already had rings on their fingers.

If you're like me and thinking of taking the plunge into Ashley Madison, I would advise wading into this cesspool very carefully. This is what I've seen, heard, and learned…

The Men Think They're More Charming Than They Are

Most of the men I've met on Ashley Madison seem to think they're Don Draper. To them, if they order the right drink (an old fashioned) and say the right things ("I work in advertising/tech/fashion/finance"), women will give 'em their panties and bend over. None of them are all that charming, and they don't know how to talk to women (saying "LOL" out loud does not count as youthful wit). How any of them ever managed to land themselves wives is beyond me.

Take "John," for instance. He was one of the first men to message me on the site. He was looking for that "special someone" with whom he could "gaze at the stars with." John was your typical Ashley Madison customer: He was married, white, well-off, and a commuter – which is a bonus, because it allows them to keep their affairs separate from everything else. After exchanging a few messages, he finally mustered up enough courage to ask me to dinner. I accepted and met him at a tacky little bar in Midtown East.


Later, as our "date" was winding down, he swiftly and firmly held my jaw in place and proceeded to kiss me. Then he offered to go down on me.

In his pictures, he looked the part of a healthy and normal middle-aged father— striped polo shirts, running shoes, and the like. Meeting face-to-face, however, was a different story. He was rumpled and tired looking. His ill-fitting shirt and khakis had bits of lunch stained into them. It was a tense meeting, not unlike a bizarre job interview: "Have you ever done this before? Why are you doing this? What's your favourite position? Favourite dessert?"

Despite a serious lack of chemistry, we trudged on to dinner – partly because I'm an optimist, but mostly because I was broke. He ordered pasta Bolognese and chewed with his mouth wide open. Later, as our "date" was winding down, he swiftly and firmly held my jaw in place and proceeded to kiss me. Then he offered to go down on me. Squirming out of his greasy grasp, I hastily declined and (thankfully) never saw him again. I haven't eaten Bolognese sauce since then.

Lesson here: These men are not smooth. They are hiding behind their computer screens to get laid. Why else would they be on Ashley Madison?

Other Women Have Set the Bar Low

Because Ashley Madison is infested with scammers and webcam girls and sugar babies, most men are elated if you give them any sort of response – even a nasty one. In order to contact prospective "dates," these men have to shell out money. (Women, on the other hand, can sit back and wait for men to pay to message them.) Your reply to their message is like a flicker of hope in the dark and lonely abyss of the internet.

Remember, this is a website for married people. You're meant to be everything that their significant other is not. Once they start messaging you, prepare yourself for venting and impromptu therapy sessions: "My wife never wants to have sex!" or "My wife is always nagging me!" It's exhausting, but there's an upside: When you're being compared with someone they've already lost interest in, it's impossible not to look great.


There are more benefits to being the "other woman." First, because these men are already married, there are no domestic or familial expectations. They're already weighed down with that, and they just want to have fun with you. Second, there is no encroachment on your independence and the life that you've already carved out for yourself. Freedom – while also having a companion at your beck and call. Third, you'll only get the best side of him and the best treatment. He doesn't have time to be anything less than a Prince Charming knockoff.

Plus, the possibility of feeling suffocated and bored, like you might in a "regular" relationship, is very slim since there's only so much that he can give. Personally, I consider that a win.

I once had a guy message me who was trying to pass off a black-and-white photo of a young Mikhail Baryshnikov as his own.

Everyone Is Lying

This is a site where lies fester. Everyone on it is already lying to their spouses, so at some point, you're bound to be be lied to also. Case in point: the photos. Men like to post photos of themselves from five years ago… which, fine, isn't so bad. That happens on traditional dating sites as well. But I once had a guy message me who was trying to pass off a black-and-white photo of a young Mikhail Baryshnikov as his own. Unfortunately for him, I recognised the picture and called him out on it. He sheepishly admitted that, no, it wasn't his photo but that friends had told him that he "resembled him." I highly doubt that.

If their profiles aren't full of blatant lies, then they're full of clichés. Here is a real sample of profiles on Ashley Madison:


  • "Looking for chemistry"
  • "Looking for adventure"
  • "I want a real woman"
  • "No drama here!"
  • "Wanna play?"

Often, their initial messages are cut-and-paste introductions, which are usually full of both lies and clichés. I once received the following message: "Weapons of Mass Pleasure… Hi! I am tall (6'1"), well endowed, and very fit bodied (175lbs). Lots of stamina and control in bed. Intelligent, charming, and well educated. I possess the gift of gab, but also know when to keep my mouth shut. Successful professional. Seek a sexually intense, passionate, fun, and friendly relationship. I live a healthy lifestyle and seek a woman who does the same. I am dominant in the bedroom. Say hello if you have an interest."

When I called him out on his (terrible) boilerplate introduction, he responded: "Lol! Got me. But you must understand this becomes a full time job if you get let it." In that case, they're all overworked and underpaid.

There's a High Likelihood of Men Getting Desperate and Weird

It goes without saying that your safety should always be a priority. Obviously, giving out personal information (phone numbers, personal email addresses) should be avoided unless you've built something serious – that goes for traditional dating sites as much as Ashley Madison. On Ashley Madison, most men are not looking to change their marriage "situation," so they'll keep quiet and move on if you're not interested – but I've had multiple experiences of guys getting weird and stalkery after I'd turned them down. It's a puzzle to me why some people on this site are so blind to the power that others have to fuck up their lives.

Remember John? After nine or ten months of silence, I began receiving messages from him again. "Hi!! Let's chat? I've been thinking of you!!" When I didn't reply, he'd send a follow-up: "Just one drink??? Let's start the New Year off right. Say yes!" And then, because men can see when their messages have been opened, he would message me again: "I CAN STILL REMEMBER THAT NIGHT AND HOW YOUR LIPS FELT. HAVE A DRINK. SAY YES."


I quickly blocked him, only to have my Gmail flooded with ardent and obsessive messages. "I didn't know what I was doing last time. I know you live downtown. I know it. I will come to you PLEASE SAY SOMETHING. SAY YES. SAY YES. I NEED THIS!" What he needed was a good blocking and some radio silence, and I gave it to him.

I wish I could say this was the only time I've received messages like this. A while back, I was chatting with a guy named "James" on a pretty regular basis. Then I got busy; work picked up, and I sort of forgot about him. Well, James didn't forget. And he wanted me to know it: "You have stuck in my brain even though our interaction has been short. I have kept you in my sights as I journey down this path of finding a girlfriend/confidant/partner in crime. I have decided on you – this is my decision and you will submit to me. My quest will NOT be complete until I have met you to see if you are the package I dream you might be. You have my personal email. WOULD BE BEST TO RESPOND THERE. USE IT. PROMPTLY." I promptly blocked him. Quest over.

I had the privilege of getting a candid glimpse into the sometimes depressing dynamics of marriage and saw that it's not for everyone—myself included.

still, You Can Get a Lot Out of It

Despite the exhausting river of shit I nearly drowned in, it wasn't all for nothing. I managed to eat and drink very well, even when I was broke. I was given insight into the lives of wealthy and powerful men, as they paid for everything with a dismissive toss of a credit card. I also had the privilege of getting a candid glimpse into the sometimes depressing dynamics of marriage and saw that it's not for everyone – myself included.

But the most important thing I saw was that most of these men – who had been lucky enough to find sweet, stable women who would put up with their unsavoury habits, fuck them, and take care of them no matter what – really didn't want to upset the balance they'd created in their marriages. And yet, there was always an excuse to cheat. I've heard it all:

  • "I got married too early"
  • "I'm not appreciated"
  • "I'm stuck in a rut"
  • "Having kids ruined it"
  • "I'm a sex addict"
  • "She's having an affair"
  • "We both settled"

At the end of the day, I had a lot of fun with Ashley Madison. If I believed in karma I'd wager to say that I would most likely pay for all of this in some way down the line. The hard truth is that I probably won't.