Olivia dates rich older men in exchange for gifts and money. She doesn’t consider it prostitution. In her mind, and in the minds of tens of thousands of other young Toronto women who have struck up similar for-profit relationships, it’s much more than a commercial exchange.
As a teen, Olivia didn’t get along with her mother, and, after dropping out of her Halifax high school, she moved out on her own and went on welfare. She discovered that her looks—bright blue eyes, perfect breasts, prairie-flat stomach—were her ticket to modelling gigs and bit parts in TV shows, but the work was sporadic and paid poorly. Two years ago, she moved to Toronto, looking for more opportunities. Now 25, she’s earning enough to pay her rent but not enough to support the lifestyle she imagined for herself.
Last year, a friend of Olivia’s told her she was seeing a man she’d met on SeekingArrangement.com, a match-making site designed to facilitate the pairing of wealthy older men with attractive young women. Over the past decade, many such websites have launched, helping women negotiate gifts, allowance, tuition, mentorship or simply a night out, in exchange for their companionship and, often, for sex. Olivia’s friend usually got a nice dinner, bottles of champagne and cash. She referred to her date as her sugar daddy and to herself as his sugar baby.
Olivia liked the idea of a rich man helping her with her career, telling her the secrets of how he became so successful, and pushing her life in the same direction. Plus, she wanted to have fun. She put her profile up on SeekingArrangement.com and, later, on WhatsYourPrice.com. The first few men she met weren’t perfect. One wouldn’t hold the door for her. Another was married. Many just wanted to pay for sex, but she eventually met a wealthy, recently divorced doctor in his early 40s who kept a small roster of sugar babies.
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Everything you’re about to read is true. I’m withholding my name to protect my marriage, but the people, the places and the dates are just as I describe. It all began in the spring of 2011, after several bellinis at a Milestones with my best friend. She giddily whispered in my ear that she was having an affair with someone she had met on AshleyMadison.com, the hook-up website targeted at married people. She pulled out her iPhone and surreptitiously showed me a picture of her paramour. He was attractive, with a chiseled face and a broad smile. He’d ended their first date by kissing her passionately—something she hadn’t experienced in years. I felt a pang of envy.
The founder of a Toronto-based dating Web site is accusing Google of sexism. No, it’s not Ashley Madison, but it’s almost as good. 
