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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.

  • Kdahl

    Any way you paint it – Its prostitution. And what is Toronto Life’s fascination with the seedier parts of Toronto? This is the second or possibly third article on “kept” women. Pick it up a notch guys. Barf..

  • huhy

    I agree with Kdahl that TorontoLife seems fixed on postitution in the city. It sells.

  • Emma VonE

    Enjoy it honey, while you’ve got it. Once you’re in you’re 30′s you’ll be unemployed, broke and living back at home.

  • disqus

    A senior writer/editor of TL uses those sites…he claims to make over a million dollars in salary lol…we saw his ipad opened on the site during a meeting…smh

  • Dáibhi Bearnard Ó Slatraigh

    So, she’s a prostitute that doesn’t sleep with them, or does she? How quaint.

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  • Hhmmm

    Maybe he was on the site checking it out for this story? Things aren’t always as they appear right

  • Hhmmm

    I see both sides of this one but did anyone else notice she’s not especially attractive? That’s what I find I remarkable about the story her Dr. is interested in more than just looks

  • hey

    A sugar daddy/baby relationship is just that…a relationship. Getting a phone call here and there to meet up and perform some kind of task, sexual or otherwise, and getting slipped cash at the end of the encounter is not a relationship it’s prostitution, plain and simple. He didn’t have to go somewhere else if he wanted an escort, he went there….and got you. What’s wrong with our society

  • AnnaVon

    oooh so much hate on this thread, I say go for it. Do what makes you happy-there’s nothing wrong with being direct. Historically, no one has ever liked a woman who was in control of her sexual prowess or used it for her own gain. It’s a bit dated to attack a woman because she’s not ashamed/subservient/subordinate/working in a job we deem appropriate for women….like PR though don’t you think?

  • Hhmmm

    Based on the story it seems like a big part of current urban culture

  • DD

    I didn’t think anything could be more trashy than the Ashley Madison article from a few months back but this is.

  • NA

    These women of course want to spin the story. Definition of prostitution reads as follows.
    I’d love Olivia to explain the difference.
    1. The practice or occupation of engaging in sex with someone for payment.
    2. The corrupt use of one’s talents for personal or financial gain.

    Paging Olivia…..

  • Indigobaobab

    Was about to remove Toronto Life from my page until I saw the comments, glad to see I ‘m not the only one wondering about the direction it’s taking.

  • Bojan Landekic

    Because of this you think something’s wrong with our society? What will you think when you discover that for your love of bacon animals suffer painfully for years and then end up being bled to death while feeling the full shock of the pain I wonder? Or the fact that Torontonians routienly ignore the legless cripple begging for change at Yonge/Dundas while on their way to buy a $600 iPhone? Are you just now waking up to all that is wrong with this “peaceful nation” of Canada?

    Welcome to Earth. Glad you were born. :)

  • Raul

    Travel and Tourism. Hahahaah. Going to go real far with that.

  • hey

    I was referring to a society in which women prostitute themselves and yet justify it as companionship or whatever they say to themselves. A society in which married people can easily find sex and answers in another’s bed rather than fix thier problems. A society in which “sugar daddies” aka Johns, can find young impressionable women with the click of a button. But you tell me I’m “not from earth” because of animal cruelty and homelesness. Riiiiight.
    Welcome to the human brain, most of use use 10%. Glad you use 2% :)

  • CAT


  • jacs14

    Definition of prostitution from MW: the act or practice of engaging in promiscuous sexual relations especially for money. Unless these people are just holding hands then I think that’s pretty clear.

  • Rex

    I think the Pink Hello Kitty in the upper right of Olivia’s photo sums up her actual position in life far better than any of the babble that comes out of her mouth. For a moment, I wondered how she could’ve missed the potentially damning subtext her playthings represented (I count five superficial pussies on that bed!), but then I remembered that context is usually beyond the comprehension skills of hookers. :)

  • Stephka

    You clearly haven’t read your history. Ever heard of Anne Boleyn? Cleopatra? Madame de Pompadour? Madame du Barry? Most of Henry the VIII ‘s wives? Dianne de Poitiers? and Napolean’s infamous mistress Marie W? These extremely powerful sexually charged and intellectual women not only ruled King’s hearts but their countries, politics and economies as well. #doyourhomework

    This isn’t any different except now it’s accessible to less powerful men like doctors and more women as per the article. Traditionally this was done behind closed (castle) doors but now it’s in front of you. Read the below and consider whether this is a reflection of modern urban culture or just same old behaviours but now more transparent. Do what your ancestors did – turn a blind eye or join in. Someone else decided to take their cut. Good for them.

  • Stephka

    Direction? haha it’s about selling paper. Interesting and clearly emotionally provoking piece. Got to give it to them.

  • Jesse

    Toronto Life is all about the peep show, over the fence at the wealthy properties and under the sheets with whomever the owners would prefer to sleep with.

  • marie

    The tone of the article glorifies this lifestyle. It would be nice to see some of the negative repercussions associated with these “exchanges”. Emotional, or otherwise.

  • mongiove

    This is glamorized prostitution made to look appealing and trying to justify it. What happened to making an honest living, working hard, sacrificing and saving? This things can easily be acquired with a little patience and time. Where have all the morals gone? Is this the best Toronto Life can do to find an intriguing topic to discuss?

  • Blueberry

    i love all the comments here and was actually thinking the same thing, but take a moment here and think about this and correct me please:
    what about when you go out on a date and pay for dinner? what about housewives? are they not paid for something? what about the men who pay her? what about men who watch tv all day long and let their wives pay for their food?
    i think this girl wants the easy way instead of getting a decent education she chose to sell her body, but arent we all slaves to one another and somehow prostitutes in our own way? think about it and let me know… (i am not agreeing with this article, just thinking out loud)

  • Guest

    what about men who watch tv all day long and let their wives pay for their food? are they prostitutes? etc

  • Guest

    i love all the comments here and was actually thinking the same thing, but take a moment here and think about this and correct me please:
    what about when you go out on a date and pay for dinner? what about housewives? are they not paid for something? what about the men who pay her? what about men who watch tv all day long and let their wives pay for their food? are they prostitutes? etc.
    i think this girl wants the easy way instead of getting a decent education she chose to sell her body, but arent we all slaves to one another and somehow prostitutes in our own way? think about it and let me know… (i am not agreeing with this article, just thinking out loud)

  • Blueberry

    what does feminism prowess and PR have to do with this story? please read a book!

  • Tony Lam

    The readership must be really stuck up to hear that much resistance to something that is considered routine in Europe and elsewhere.Prostitution are defined by how much red tape you did NOT have to go through to get sex. It started when Mr. Caveman had to gave away half of what he hunted to get the other half cooked, those are all our ancestors.Lots of religious baggage in Toronto.

  • Daniela

    I found this article very intriguing. It is easy for someone who reads news online to skim through a lot, but I read this article from beginning to end. Reading about these girls, I think we all have witnessed mild forms of a give and take relationship. What’s wrong with admitting that you want a lifestyle you cannot afford?

  • MsDragonSlayer

    thank goodness just a piece of paper makes it legit.

  • MsDragonSlayer

    some people just don’t believe they have to put a ring on it to get the perks. Sorry housewives, but you are all prostitutes as well. You just sleep with one man and take half.

  • MsDragonSlayer

    You mean the worlds oldest profession is somehow new?

  • AlyssaMoh

    Ouch. Realize you’re trying to defend women, but throwing the other half under the bus is kind of…not very helpful?

    Most women work jobs and do housework as well. And even if they don’t have a job, they are raising children. you know..performing activities involving mental or physical effort done in order to achieve a purpose – or “work” as it’s known.

    Calling housewives prostitutes is insulting for not only the women, but the men they’re married to – like the man has no other thing to offer the woman other than finance. He’s not, you know, nice or funny or interesting… he’s just the sum of the numbers on his T4.

    People make choices. People will judge other people based on their beliefs, progressive or not; I guess that’s why I can’t wear a snuggie to work event though ITS 17 DEGREES IN MY OFFICE. It’s just the way the world works.

  • Valerie Feria Isacks

    Probably, and there’s nothing wrong with that either so long as it’s what the woman consented to! If she didn’t consent to that and she wanted to be part of a relationship with a double income then he’s breaking the agreement and is a lazy bum.

  • Bulder

    Tats different ,they are in Relationship !

  • FireBoy

    This basically describes every woman.They trade their …. against food, protection, security, child support, …. on different levels…. That’s in their nature. They only call it prostitution when they directly exchange it with money. So get used to it

  • williampenn

    “Tens of thousands of other Toronto women…” In a city of 2.6+ million, with half the population female, and one-fourth of those fitting the “sugar baby” age group, with just 25,000 sugar babies, that’s 1 out of every 13, or less. Wow! The city’s a virtual brothel!


    i think that women in this day and age have it pretty easy!! all they half to do is spread their legs and they get whatever they want!! including half of the husbands assets !! is this fair?? don’t think so women just go after men for their money so yes they are prostitutes!!!!!!!

  • Freebie

    Calling women prostitutes is like calling men Johns, which is insulting for both men and women. Its like calling your dad or brother a John, or like calling your mom or sister a prostitute (though no one thinks that way about their family – just outsiders)

    In 2013, with neoliberalism and outsourcing and stagflation of wages, everyone has to work – no one has it easy, or they end up homeless. I volunteer at a shelter that has men and women and even children. No one has it easy in life – there is nothing that guarantees you won’t face some sort of adversity.

    When I look at the relationships my friends and I have, I suppose we are fortunate in that we all have healthy relationships.

    It’s sad when I hear some girls say “all guys are dicks and just looking for sex” and then hear single men say “All girls are sluts just looking for money”. You gotta wonder what the disconnect is. These are the people who have felt slighted or carry hurt in them.

    Even though this story is a “shock piece”, it always reminds me how lucky I am that I had hardworking parents that made my brother and I strong independent people. The idea of depending on someone else long term would embarrass me, and my family would be rolling in their graves if either of us, after all they worked for, took handouts.


  • Freebie

    And then mom and dad will be selling their Toronto home for $$$ to retire and you won’t have a place to live, and they’re not going to give you handouts like when you were 20.

  • Angel Carpio

    Isn’t the world’s oldest profesion to be a hunter?