The Two-Timers’ Club

The Two-Timers’ Club
Adultery has never been easier, thanks to a Toronto Web site with 2.7 million users

Cheating on a spouse has never been easier, thanks to Ashley Madison—the Web site that facilitates philandering for 2.7 million users. How Toronto changed the rules of adultery

The Two Timers' Club
Adultery has never been easier, thanks to a Toronto Web site with 2.7 million users

Somewhere in Toronto as I write, there’s a busy executive who might be dropping one of her kids off at karate lessons, or pitching a work project, or discussing the in-laws with her husband, or receiving oral sex from a virtual stranger under the table in a pub. To roughly 380,000 men in the GTA she is known, simply, as Saucy Sue. These men are married, too, and unbeknownst to their wives, or to Saucy Sue’s husband, they all spend a chunk of their time—often at work—flirting on a Web site called Ashley Madison, whose promotional motto is “Life is short. Have an affair.”

Saucy Sue, who won’t reveal her real name for obvious reasons, is a marketing manager living in Leaside. She found out about Ashley Madison from a steamy TV ad that she saw with her husband last summer. “We had a good laugh about the slogan,” she says. How ballsy it was, to promote adultery that way. But privately, she was kind of intrigued. “I’d often thought if the absolutely right opportunity presented itself on a business trip, or something like that, I might have taken it,” she muses. “But it’s very difficult, as a married woman, to let people know you’re open to other possi­bilities without exposing yourself to judgment.”

Not that Saucy Sue doesn’t love her husband. She does. They’ve been together for 14 years. But marriage is marriage—it can get a little flat, a touch stale, especially after the children arrive. Your man may love you, but he no longer makes you feel like a temptress, and maybe that’s a part of yourself that you miss.

One night, when her husband was working late and her pre-schooler was in bed, Saucy Sue impulsively stole a peek at Ashley Madison on her laptop. The site, which operates out of a suite of a dozen offices at Yonge and Eglinton to serve the furtive needs of married people all over North America, is easy for tentative, noncommittal visitors to browse. No need to pay, or to post a picture, or even to say much about yourself at first. Just dream up a nickname and a tag line—“yearning for more” or “lonely in bed”—maybe check a few boxes about what you’re looking for: candlelight, hot oil massage, erotic chat. Indicate whether you’re seeking a long-term or short-term affair. Browse away.

“I look good on paper,” says Sue. “I’m five foot six, 130 pounds, 33 years old. About 30 seconds after signing up, I was bombarded with multiple offers to chat. I joked with one guy about threesomes and thongs and about him delivering pizza to my house and other cliché porn scenarios. I got a rush of adrenalin from feeling sexy and witty.”

Pretty soon, Sue put up a picture of herself, evocative but blurry so that no one would recognize her, and men—“tons and tons and tons of them”—began paying to send her mes­sages. (For $49, you can buy 100 credits on Ashley Madison, with each personalized message you initiate costing five of them.) Wander through the site’s silent, beckoning crowd of 2.7 million members, and you’ll note that most of the women show their photos, whereas most of the men do not. This is odd, since the men outnumber the women by three to one. The women should be calling the shots. But it’s the men who remain shadowy silhouettes with tell-nothing names like “Fireman Bob” or “Oral Dave,” a default declara­tion apologizing for the absence of a mug shot: “Please respect my discretionary requirements.” If they choose, they will send you a key icon and invite you to see what they really look like in their “private showcase.”

Then, surprise! Out pops some soft-bellied guy holding a Blue at his cottage in Muskoka, or a man in his 60s frantically balancing on a medicine ball to prove his physical prowess. It’s like a disconcerting advent calendar. What’s behind this window? Chocolate? Or a doofus? Sometimes, the only thing men display in their private showcase is a close-up of their penis, erect and oiled, as if all this time, you’ve just been dying for a dildo that can type.

The first man that Saucy Sue agreed to meet was a Bay Street boy from the west end. (“A massive percentage” of the attractive men on Ashley Madison work in finance, she notes.) But when they finally got together for coffee, Sue found herself more attracted to her latte than her partner in sin. He made several persistent and increasingly forlorn phone calls. “In the end, I had to ‘break up’ with him,” she says. “I did a lousy job of it.”

Unlike the office, or the neighbourhood, on an Internet site like Ashley Madison, your prospects for having an affair are infinite. Even as you select one or two candidates for flirtatious little talks, dozens of other suitors are circ­ling. The queue grows. Messages, inquiries, little key icons keep winging into your mailbox like mayflies in mating season.

“I was e-mailing back and forth with another guy,” an engineer from the Annex, explains Sue, “who wrote these beautiful messages…very descriptive scenes of how our encounters might go. I agreed to meet him.” They met at the Brick Works and shared an umbrella as they walked under a gentle rain through the ravines. For Sue, the encounter was simultaneously nerve-racking and exciting. “It was like being a teenager all over again,” she says. “It was awesome. When he did finally drop his bag on the ground, turn to me and pull me close for a kiss, I could feel my knees shaking. It was sort of a jumping-off point. I had made the decision to cheat.”

The Two-Timers’ Club

Cheating, new research suggests, is becoming a common phenomenon in North America. According to studies at the University of Washington, roughly 20 per cent of men and 15 per cent of women under the age of 35 admit to having been unfaith­ful in their still-fresh marriages. There has also been a big jump in the number of adulterers, both male and female, over the age of 60. (Coffee, tea or Viagra?)

The numbers for Ontario are even higher. According to Leger Marketing data from 2007, 30 per cent of us admit to having cheated on a partner. Why might that be? Are we more unhappily married, more adventurous, or merely ahead of the curve on the zeitgeist? One thing is certain: Toronto is the city that altered the rules of the adultery game.

Ashley Madison, the first cheating site on the Internet, was founded by Darren Morgenstern, a 45-year-old high school dropout from north Toronto with an entrepreneurial bent. In 2000, after a few years spent flipping domain names on the Web, Morgen­stern was casting about for a new business to start when he noticed a gap in the market for dating. Amid the flourishing of such sites as Lavalife and, there was nowhere for would-be philanderers to go. Or, more specifically, nowhere for them to be above-board and unapologetic about their desire to get a little on the side. Adultery, unlike pornography, had no destination on the Web. And yet, the Web was its perfect realm.

“On-line, there’s this amazing veil of anonymity,” Morgenstern says. He did a little research to see if there was some other way to bring hopeful adulterers together, like speed-dating or an old-fashioned match service, but overwhelmingly people said that they wanted to do it on-line. “They didn’t want to walk through a door with a shingle over it saying ‘Cheaters Come Here.’ ”

So, in January 2002, Morgenstern ponied up $10,000 to launch the site, announcing it with small-print ads in the Toronto Star and in the classified section of this magazine. “You didn’t need to speak up loud,” he says. “The people who were looking were looking.”

By the following summer, the site was attracting media coverage, which, in turn, spurred “a quantum leap,” he says, in members (from 60,000 to 550,000). Morgenstern decided to broaden his geographical base. The challenge was to figure out how to “brand” adultery, so that he could advertise more widely without coming across as a profiteering home wrecker. He decided to produce a pseudo-scientific infomercial called “Perspectives on Infidelity,” which he aired on such channels as OMNI, CHCH and the Fox affi­liate in Buffalo. In the late-night ad, Morgenstern, who resembles a slightly down-market version of Tom Cruise, stands against a backdrop of sparkly dark blue curtains, attired in a stiff navy blazer and open-collared shirt. He gestures with self-conscious theatricality—first turning to this camera, then to that one—as he recites facts about humankind’s historical disregard for monogamy.

“Is this a bad thing?” he asks the camera. “It’s probably not good or bad, just reality.” Then he tries to distance himself from the moral relativism he’s just espoused: “Do we think that people should cheat? Of course not. Are we encouraging them? No. If your relationship is in trouble, by all means, get counselling and try to repair it any way you can. But if you’ve already made up your mind…then log on to…. If, after browsing our Web site, you decide to stay in your relationship, well, good for you.” Ashley Madison’s own research shows that the women who visit the site are often in the first or second year of their marriage and are likely having panic attacks about their commitment, while the men are struggling with a seven-year-itch. It’s doubtful that either have thought things through.

By 2007, Ashley Madison was generating impressive revenues and Morgenstern cashed out, selling the site (for an undisclosed sum) to a Toronto investors group called Avid Life Media, who have proven considerably more sophisticated and aggressive with their marketing. Avid Life also owns the controversial site Hot or Not—where users submit photos of themselves and have them rated by their peers—as well as a couple of sites devoted to green living and home renovation. The company, which was formed, initially, simply to buy Ashley Madison, has now grown to employ 60 staff and is scrambling to assemble a board of directors. At its helm is an articulate, 37-year-old Osgoode law graduate named Noel Biderman. Crisply and casually dressed, he seems very much a member of his own generation of deft and facile financiers—those who grew up in a world without many fixed taboos and can surf that world for untapped sources of profit. Biderman is like the young American owners of, which enables its users to post toilet jokes to their hearts’ content, or the original purveyors of Hot or Not, or indeed the Wall Street brokers making default credit bets as if the stock market were a casino. “It’s just a business for me,” Biderman likes to say.

His office on Yonge Street is small and unadorned, with little decoration beyond framed photos of his two little tow-headed kids. On his desk, the day that I went to see him, lay a dour and misanthropic novel by Philip Roth (The Dying Animal) and a book from the classic children’s series Frog and Toad, which he had picked up downstairs at Indigo.

The Two-Timers’ Club

Prior to our interview, Biderman had sent me a YouTube link to an American news story. ESPN, according to the story, had just asked its affiliates to pull an Ashley Madison commercial off the air. “I’m never surprised when someone rejects our ad,” Biderman says. (He still gets spurned by mainstream Toronto radio and television stations.) But he was surprised to be rejected by a network that runs ads for erectile dysfunction treatments and male enhance­ments. “They didn’t seem to be people who would feel sensitive to an issue around infidelity,” he says. “Their audience is male, beer drinking, so who was being offended?”

Beer and Viagra apparently remain more palatable than adultery. North Americans have always been skittish about transgressing their family values. The reason Ashley Madison took off in the first place, Biderman speculates, is that it was founded and fine-tuned in Toronto, a particularly cosmopolitan city, home to the inter­nationally popular dating site Lavalife, to such posh sex clubs as Wicked, to Condom Shacks and swingers’ parties, and one of the first municipalities in the world to allow gay marriage. “There’s always a timing issue to ideas,” he says. “The fact that Darren Morgenstern proved this in Toronto allowed me to effectively execute a U.S. expansion strategy and make it look so meteoric, right? Had we started in the U.S. or in the wrong marketplace, it could have been really problematic.”

The ESPN pullback generated press coverage, which always works to Ashley Madison’s advantage. In October 2007, Ellen De­Generes riffed on their Beverly Hills billboard. “Life is short. Eat a cake,” she joked. “Life is short. Rob a bank, then go to jail where life is long.” The site’s female member base jumped by 8,000 that day. Likewise, 150,000 new members visited the site in the week after Ashley Madison was forced to pull down a billboard from New York’s Times Square (the building’s owner protested). Biderman loves dreaming up new ways to market the company, meeting with Hollywood producers about reality TV spinoffs and “dramedy” adaptations.

Last March, when New York governor Eliot Spitzer found himself engulfed by scandal for hiring a prostitute, Biderman bought a full-page ad in the New York Post, positioned as an open e-mail to Spitzer, with the heading “We Told You So.” It needled the gover­nor, saying that he could have got away with it if he’d only used Ashley Madison. Then Biderman went on Larry King Live to expand on his cheeky point. New York is now his third-biggest paying market, with Los Angeles in first place and Toronto in second.

The publicity also generates hate mail, of course, and there are plenty of exclamations of sorrow on Internet message boards and even on-line petitions from women and men who’ve been “done wrong” by their cheating partners due to his site. Biderman’s rather lawyerly counter-argument is that there are reasons that people behave this way, “and nobody wants to talk about that.” He’s referring to people in positions of power with a great deal to lose who still go ahead and risk losing it. Whether they’re driven by intense emotional or sexual needs, or are suffering from delusions of grandeur is hard to gauge.

Biderman himself is trying to steer clear of the Ashley Madison lifestyle. “I hope I’m one of those people that can make it through marriage,” he reflects, “but I realize that it’s an incredibly challenging feat, and that means you have to work at it.”

Late one night, while the neighbour’s dog howled all alone in his yard, I stared bleary-eyed at my Ashley Madison inbox, where I’d managed to accumulate several hundred messages in less than a month while posing as a desperate housewife for this article. Some of the guys are right in my face, as clumsy and excited as puppies. But many are conflicted, circumspect, careful. They don’t know how to proceed, or even if they want to. “Always feel stupid doing this,” one man wrote to me. “How do you try to portray yourself without sounding boastful or dishonest? I am a 48-year-old, fit, successful, well-balanced guy. I gather I am good looking but who knows. I love to golf, read, work out, travel, etc.”

He wants one more go-around at real intimacy, he suggested in his profile. Maybe he and his wife have a cold war going on in the bedroom, or their chemistry is kaput; he doesn’t say. “You are far more brave than I putting your picture out there,” he messages. “I am overly cautious as I have so much to lose. The other day, one of the people from accounting came into my office and asked how they should code ‘Ashley Madison’ on my credit card statement. I just about died.”

We traded lists of five things we want to do before we do, in fact, die, as a way of getting to know each other better. I want to learn Latin dancing and go on safari in Africa; he has already taken that safari, but wants to learn a new language and see the Nile. He then gave me an e-mail address for further contact. Later, when I went to check his profile again, it had been snatched down, as if he’d had a sudden case of heebie-jeebies. My husband kept poking his head into my home office: “Aren’t you finished researching that article yet? Don’t you have enough material?”

According to Biderman, the timing of the Web site’s activity is completely consistent: Monday mornings, and after every major family holiday, the traffic spikes. A lot of his log-ins come from downtown offices. (Although a larger number of women are logging in from the suburbs. The next busiest spots are York, East York and Oakville.)

The women, on average, are in their late 20s and early 30s, the men in their late 30s and 40s. This was not my experience on the site, but maybe that’s because I attract the older crowd. I messaged back and forth with a cop in the middle of a distressing custody fight. After a while, we realized that we were merely sharing depressing tidbits about our extended family travails without actually having a smidgen of fun.

I chatted with an urban planner near Malton who despises David Miller, and a graphic designer living downtown who spells “you” as “u,” which pretty much ended my interest in further conversation. It’s hard to determine from the banter whether you’d bother with any of these men in real life. An affair, after all, is entirely about chemistry—otherwise what’s the point? One businessman who was witty and amusing proceeded to send me an erotic, Penthouse Forum–style letter, and I found myself thinking, Well, this is novel, but about whom would I be fantasizing if I respon­ded in kind? What if he’s, like, the dog Brian on Family Guy? What if he’s Rex Murphy undercover? Two journalists scripting X-rated scenarios back and forth like a couple of towering idiots. I mean, I have no idea.

At this point, I compared notes with a veteran user of Ashley Madison, Linda G., a straight-talking, seen-it-all 44-year-old blonde who manages an accounting department in Mississauga and resembles Melanie Griffiths. She is on the site with her husband’s knowledge—he likes to watch. “If there’s an interest to meet, get off the site and pick up the phone,” she advised me briskly, turning her mouth away from the receiver at one point to remind her teenaged son of his chores. “I can learn more from them in one minute on the phone than hours of typing. I had one guy,” she recalled, “who used a picture that wasn’t of him. When I met him for the first time, I laughed. He tried to justify it by saying that the picture he’d used on AM was of a cousin, so at least they were related. That’s just nonsense. Even though this whole thing is a lie, there has to be some truth to it.”

She talked about the men who send messages from the airport on their BlackBerrys, summoning her as if she’s a free hooker prepared to show up anywhere for anyone with her legs spread. We agreed that you have to grow ruthless in pruning your inbox messages, instantly deleting come-ons from men who are too young or too old or who use the words “lady” and “gal.”

Most of the men that I encoun­tered on the site were firmly attached to their spouses, or so they declared. None wanted to upset the familial rhythm of their lives; they just wanted something else, something extra. But when they spelled out what that “extra” was, it usually wasn’t a quick bit of tail (those men probably send messages to “Puck Bunny”). Their visions were far more romantic and emotional. They wanted to find “that spark” again in their lives with a woman who was intelligent and sensual and a good conversationalist. To me, it sounded like they were hoping to fall in love. Were they pursuing two fantasies in this sense? The fantasy that the perfect lover exists, and that you can love her and still love your marriage? “Sometimes,” Linda said to me, “it takes a little straying for you to realize how good what you’ve got really is.”

Linda still hasn’t found what she’s looking for on Ashley Madison. But Saucy Sue has. She’s been seeing the same guy now for two months. After her surprising make-out session at the Brick Works, a third man appeared who appealed to her most of all. This third guy was the one who astonished her by giving her oral sex beneath the table at the pub. How long she can maintain her affair is a wide-open guess. To judge by the messages I continue to get—“Where did you go?” and “I miss you”—the men that I chatted up haven’t found the woman of their dreams yet. Noel Biderman, who reads extensively about the sociology of infidelity, has a theory: “There’s a staged approach to having an affair,” he muses. “Going out there and testing the waters by putting up your profile is very different from meeting in a hotel room. Maybe people who are predisposed to going down this path will test the waters and change their mind. For them, the service is cathartic.” And maybe there’s a little cash to be made from their yearning.


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