The Two-Timers’ Club - Page 2 From the January 2009 issue

Image credit: Don Weber

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.

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