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Girlfriends for Hire: the rules of Toronto’s new sugar daddy economy

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.

The Sweetened Life

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, 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 and, later, on 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.

For their first meeting, he booked a room in the Trump hotel. He was not especially handsome, but he was well-groomed. They had drinks together in the hotel room and he quizzed her about her goals and interests. There was no sex, no physical contact. At the end of the night, he gave her his number.

They’ve since gone on two or three dates a month. She tells me she has a powerful intellectual attraction to him. She likes that he’s generous with his children—she thinks he has two or three, but doesn’t know for sure—and that she can talk to him about pretty much anything. She likes that he wants her for more than her body.

For the most part, he decides when they meet. Sometimes they have sex—good sex, sometimes with another woman, or two—but often they just grab dinner, or meet up for a drink, or talk long into the night. Whatever they do, or don’t do, her sugar daddy always hands her $500 at the end of the encounter. He slips it into her hand, delicate as a sparrow’s wing, and says, “For you.” Olivia sees it as a gentlemanly gesture; she never negotiated the amount, though many sugar babies do. She doesn’t consider herself to be an escort. If that’s what he wanted, she says, he could go somewhere else.

For many sugar daddies, the idea of hiring a prostitute is unpalatable—they don’t like the open acknowledgement that a woman is with them for the money or that she is, very possibly, faking her sexual pleasure. Sugar daddies want a more authentic ­relationship. They often like to see themselves as the white knight—the guy who makes it possible for a young woman to go to school, get her dream job or experience a chic lifestyle that would otherwise be unattainable. It’s not exactly dating, but a form of pampering.

Sugar daddies have been around probably as long as the world’s oldest profession. The term gained modern-day ­traction with the 2002 publication of Sugar Daddy 101, a popular how-to book by Leidra Lawson, an Atlanta-based veteran sugar baby, who leads workshops on how to navigate the sugar world and appears at sex conventions and conferences. To the people who call themselves sugar daddies and sugar babies, the word primarily connotes a lifestyle: an exclusive club for no-strings couplings.