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

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.

Editor’s note: Since our publication of “The Sweetened Life,” in April 2013, it has come to our attention that two of the minor sources mentioned in the piece, Steve and Melissa, misrepresented themselves to Toronto Life. Both used fake names. As it turns out, “Steve” was an acquaintance of Noel Biderman, now former CEO of Avid Life, the parent company of Established Men and Ashley Madison. Though Steve later provided documentation to prove he was an active user of the site, he lied about a number of personal details. “Melissa,” also unbeknownst to us, was one of Biderman’s employees. We have not been able to reach her for comment. Toronto Life takes full responsibility for the errors. Apologies to our readers.

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.

In her book, Lawson recommended women meet potential sugar daddies at upscale furniture stores and restaurants, health clubs and financial centres. “Before going inside a restaurant, conduct a car check to see how many fancy cars and limos are parked outside,” she wrote. Particularly, women should look for Ferraris, BMWs and Benzes.

Lawson still receives speaking requests and fan emails, but much of her book’s practical advice has become obsolete. Now, when you Google “sugar daddy,” hundreds of websites pop up. There are life coaches who offer instructions on how to be the best sugar baby you can be. One, Taylor B. Jones, has a Power­Point presentation dubbed “The Blueprint for Sugar Daddy Dating.” There is even a website called Sugar Daddy Finder, which includes a free e-book with such sage advice as: “High heels make your legs look long and lean [and] your ass look spectacular and pert, and can take any outfit to the next level.”

Two of the most popular sugar websites are SeekingArrangement and Sugardaddie, both U.S.-based but active in Canada, and Toronto-founded Established Men, whose parent company also operates Ashley Madison, the cheating website for married people. Each site offers the same core service: to help financially strapped young women meet older men who want to shower them with gifts, travel and cash. SeekingArrangement also asks women to include their ideal monthly allowance in their profiles; men are asked to include their yearly income, net worth and monthly sugar baby spending budget. Relationships are dubbed “mutually beneficial arrangements.”

Brandon Wade, the founder and CEO of SeekingArrangement, is a 42-year-old once-divorced MIT grad. His wife, Tanya, is a gorgeous 27-year-old Ukrainian. They met when he interviewed her for an administrative job at SeekingArrangement. When I ask him about the difference between sugar babies and hookers, Wade says that his mother, a housewife, has always received an allowance from his father. Does that make matrimony a form or prostitution? “In a sugar relationship,” he says, “it’s all about, ‘What sort of value is this person really adding to my life?’ and ‘What sort of value am I adding to their life?’ ” The sugar lifestyle is sneered at by prudes, he says, because it’s so up-front about the give-and-take. Whatever the prudes think, the lifestyle is ­catching on.

Toronto is a sugar-friendly city. Established Men’s membership has grown by more than 80 per cent each of the past two years. It has 79,000 members in the GTA (accounting for one third of its Canadian membership); roughly 26,000 of those are men and 53,000 are women. Toronto is the top sugar daddy city in Canada for SeekingArrangement as well, with a penetration of two sugar daddies for every 1,000 men. Toronto sugar daddies earn a self-reported annual income of roughly $250,000 and have an average net worth of $5.3 million. They include senior executives, entrepreneurs, and people in the finance or sales and marketing sectors. Close to 40 per cent of the men on Seeking­Arrangement are married, and, in recent years, their average age has dropped to 40—defying the Hugh Hefner stereotype. On average, Toronto’s daddies spend $4,027 a month on their women.

Sugar babies, by contrast, tend to earn less than $34,000 annually and work in retail or restaurants, or are students. Many women on the sites are looking for men to pay their way through university, while others are looking for somebody to pay off their student debt. There are women in their 30s and 40s on the sites who are divorced and want to be indulged, have deadbeat ex-husbands, or are just tired of going dutch. A surprising number of women are in it for new breasts (a common enough desire that it inspired a website called, which connects “donors” with women seeking augmentation). Lawson, like others I spoke to in the sugar world, attributes the growth in popularity of the lifestyle to a combination of the tight economy and loosening morals. It is both harder and easier for women to live the luxurious lifestyle they want.

Lawson also believes that the flourishing of Internet porn is responsible for the allure of the sugar lifestyle. Regular women see porn stars such as Jenna Jameson and James Deen as mainstream. They don’t operate underground; they’re media darlings with bestselling books, TV shows, Hollywood resumés, websites and huge Twitter followings.

To meet sugar people for this story, I joined Established Men as Lauren288. At first, I didn’t bother uploading a profile photo; I just described my body type as “average” and noted my age, 28. I was instantly pinged with dozens of messages and chat requests from men. After a few visits to the sites, I became so curious about the intricacies of first contact that I added a photo.

While women can sign up for free, men are required to pay for their accounts—$79 per month on Established Men and $60 on SeekingArrangement. On SeekingArrangement, men can pay an annual $1,250 fee to have their incomes verified—a selling point for babies who’ve been burned. For $25, the site also offers background checks for both men and women. Members who pass get an icon displayed on their profile that signifies they have not been convicted of any crime, particularly sexual assault or domestic abuse.

Despite these attempts at transparency, the site feels like an elaborate make-believe game in which money and sex have everything and nothing to do with it. A lot of the work in sugar dating is about maintaining the sweet veneer while subtly haggling over the exact benefits of arrangements—a rather delicate task. “The more personal you make it,” says Lawson, “the less it seems like it’s about money—I know that sounds silly, a bit counterintuitive—but it really makes it better.”

The innocent façade mitigates the lingering sense that arrangements are ultimately financial transactions. Sugar daddies seem more lonely and sweet than lecherous and creepy. The men who contacted me were intent on romance. One 39-year-old wrote: “I must say that you are absolutely breathtaking, and yes I know it sounds like a rehearsed line (it may very well even be for some), however, there is no other way I would describe you.” He gave me his cell number and promised “interesting conversation, tales of my adventures, a strong set of arms, and an open heart and mind.” In my short time on the site, I was never asked for sex directly, although one man from Kitchener confessed, “I am looking for that elusive friend with benefits. Sex is easy to find for me, but passion is what I really desire.”

Sugar daddy profiles often have startlingly specific requests. I found Sinbad, a 66-year-old Toronto man with a declared net worth of $2 million who described himself as a “wealthy Asian professional male, semi-retired, divorced with a daughter in university.” He said that he could be an excellent career mentor. And he had a preference for sugar babies who could ski or play tennis. He would not see anybody without proof of current university enrolment. One recently divorced 58-year-old explained that he owns a two-bedroom condo in the heart of the Entertainment District and wanted a sugar baby who would live in the condo—“separate bedroom, for your privacy when we are not ‘benefiting.’ ” He’d provide everything, including food and an allowance.

The sugar world is wary of outsiders. There were men and women who agreed to talk to me as a journalist, then never returned my phone calls. A couple of them gave me their number, answered the phone and said they’d call right back but never did, and never answered the phone again. Women asked if I would pay them and refused to participate when I said no. Those who would talk to me wanted to do so only by phone. Most were afraid of being judged or stigmatized. (Even Brandon Wade, the Seeking­Arrangement founder, operates online with a fake name; his real surname, which he uses in other business dealings, is Wey.)

Most men who agreed to be interviewed asked me to withhold their last names, certain that the discovery of their lifestyle would harm both personal and business relationships. One, a 50-year-old management consultant, told me he had a high-profile job on Bay Street. Over the phone, he talked about his motivations for joining the site. Primarily, he said, it’s for the sex, but it’s also about ego: his 28-year-old sugar baby is a knockout. He claimed he had never used a prostitute and hates it when women simulate sexual pleasure. He pays his baby $500 each time he sees her, which is only twice a month because he is very busy.

Before we got off the phone, he grilled me about the young women I’d interviewed. He wanted to know if he was, comparatively, paying too much, and if I thought he was being too forward when he asked sugar babies on the site out to lunch. How should he approach them? In fact, SeekingArrangement membership studies show there is a 50/50 split between babies who want only gifts and travel and those who also want an allowance. Established Men doesn’t permit its members to offer or ask for allowances on the site, because that would give it an escort-like feel, and the proprietors would rather members form arrangements based on mutual attraction.

Many sugar daddies prefer to seal the deal by paying for trips, dining, shopping and the occasional bill. Steve is 41 and divorced, has two children under 10 and works in real estate. His sugar baby is 24. He likes spoiling her with things she can’t afford on her own. Harbour Sixty, he says, was eye-opening to her. He also takes her on shopping sprees to Holt Renfrew and other Yorkville boutiques. He finds it exciting to give her experiences she has never had before. He recently took her on a two-day trip to Las Vegas, where they stayed at Caesars Palace, gambled, saw shows and dined at fancy restaurants. Steve figures the weekend bill, not including the flight, came to roughly $2,000, pocket change for him, but extravagant to his sugar baby. “Being in a marriage for a while, I didn’t get the thank-you, the gratitude,” he says. But now he does. This is something I hear a lot, not just from Steve. He adds that he doesn’t mean to sound arrogant, but he is certain she is not just with him for the money. Steve believes he has great advantages over 20-something men, most of whom haven’t quite learned how to treat women and are not as ­successful.

Baby profiles show a similar gamut of motives. The majority of women are up front about their expectations. Danielle, a 20-year-old U of T student on SeekingArrangement, wants a monthly allowance of $10,000 to $20,000 “plus expensive gifts or vacations.” In return, she adds: “I’m open to what you want in exchange.” Another young woman, 25-year-old Gina from Windsor, asks for a $5,000 to $10,000 monthly allowance. ­“Realistically,” she writes, “I hope to find a connection with a man who treats me with respect and values a kept woman.” Cass is among the youngest allowed on the sugar sites: an 18-year-old who enjoys shopping, tanning, travelling and sports. She wants someone to spoil her with “wonders”—and pay for school.

One U of T grad, 23-year-old Melissa, tells me she joined Established Men because she considers herself old-fashioned—the type of woman who loves Audrey Hepburn movies and “gentlemanly stuff” and believes men should pay for and do everything. She figures if she were dating a man her own age, in the same financial situation—working as a server and paying off student debt—they would have a boring routine of eating pasta while watching Netflix every night.

Her life is much better with David, her 38-year-old investment banker sugar daddy. In the two months since they met, they’ve gone to New York and San Francisco, and made plans for a four-day ski vacation to Mont Tremblant. They flew first-class to San Francisco, where they rode the famous cable cars and David bought Melissa a snow globe souvenir. It was a working trip for David; while he was at meetings, Melissa took his gold card and went shopping. She bought a nice dress for dinner, some shirts, more souvenirs and a pair of boxers for him. Melissa says she wasn’t too extravagant because she knows it takes a lot of trust for a man to hand over his credit cards. “I like him very much, and I admire him,” she adds. “So I wouldn’t want to screw him over.”

Recently, he bought her a gorgeous white winter coat. “I call it my Anastasia coat,” she says, “because it makes me feel like a princess.” Melissa does not deny that money is a big factor in her relationships. While she finds David’s confidence and chiselled shoulders sexy, she wouldn’t date him if he wasn’t wealthy. She plans to enter Ryerson’s travel and tourism program, and, if the two are still dating next September, she is sure David will help pay her tuition.

Of all the experiences Olivia’s sugar daddy has given her, the night of her 25th birthday was the best. He took her and another of his sugar babies to Yamato, a Japanese restaurant in Yorkville. For a birthday gift, he gave her a book, The Law of Attraction, a deck of tarot cards and a purple wall hanging that reads, “I connect with spirit. I invite sacred transformation. I embrace the unity of all beings.”

They had seats at a counter where they could watch the chef cook their kobe beef rose-petal rare. To keep the moment forever, she captured it all on her iPhone. She also photographed the bill, when it came: $946. Later, they went to the Park Hyatt, where he had a bottle of Dom Pérignon and a chocolate cake waiting. Olivia took a picture of both. The entire night cost close to $2,000.

Before she met her current sugar daddy, Olivia had exchanged emails with a man who promised her everything. His profile picture showed him holding a fan of $20 bills. He wanted to buy her a condo and a car, but the only person allowed in the condo with her would be him. She would have to agree to see him a minimum of 18 times every month. She realized he wanted to own her, like a pimp.

She’s constantly assessing and reassessing her motives for participating in the sugar lifestyle. Though she dreams of material things, she also believes that if a person focuses only on the material side of life, “karma will bite that person in the ass. You lose the real you.” She doesn’t want to lose the real her and often replays conversations or events from her sugar life to close friends, asking them to weigh in on how it will affect her cosmic scale.

The sugar baby lifestyle isn’t her long-term financial plan. Most sugar relationships fizzle after a few months. Some last up to a year, or even longer—depending on the connection, or, more typically, the demands. Olivia has no dreams of marrying her sugar daddy but also does not want to end the relationship any time soon. She is careful about not asking him for anything directly, partially because she doesn’t want to scare him off, but also because she doesn’t want to rely on him for everything.

Last December, she considered breaking her rule and asking him for extra money. She had moved into a new apartment and her deposit and first month’s rent totalled $2,400, which was fine, she says, because she had that amount saved. But she didn’t have enough to pay January’s rent. She knew that her sugar daddy would pay it, if she asked. After all, he had bought another one of his babies a car.

She found a way to pay it herself, but during their next date she mentioned the financially draining episode in casual conversation. When her daddy left that night, he slipped $600 into her hand instead of the usual $500. This time, he added, “I hope that helps.” He always takes care of her.