Thurston Von Moneybags (not his real name) was scammed once by a girl in Houston. He had arranged to meet her so that he might size her up and determine whether he wanted to give her a monthly stipend in exchange for regular sex and sometimes maybe dinner. In other words: Was there chemistry? Was she blonde and blue-eyed, the way he liked them? Was she thin “but not anorexic, a shapely body, you know?” Could he talk to her? That was very important. It was a little important. It wasn't that important. Anyway, she asked for money up front, and he sent her $800. She didn't show to the meet, and that's the last time Thurston Von Moneybags ever got hustled again. Now he meets the girls for lunch before he offers them an ahem arrangement, and he is very clear. He doesn't give them money until their second date, when they're in the bedroom, which sometimes feels bad, which sometimes chips away at his this-isn't-prostitution line—Thurston was raised Catholic, after all—but what's the alternative? Getting scammed again? I don't think so. A thing you should know is that there are very few people to root for in this story.
Which is not to say that old Thurston is a bad guy. He went to some of the best colleges and grad schools. He loves to treat a lady well. Just ask his ex-wife—even she wouldn't say a bad word about him. But you know how it is, the fires dampen, and he wanted a lot of sex—“I'm Italian! I have this gene!”—and eventually they divorced, and Thurston wanted something, mainly a lot of sex without having to beg for it, and to be found attractive again. But on all the traditional dating sites, the women didn't just want sex. They wanted companionship and respect and a relationship with a forward trajectory. They wanted hand-holding and flowers and surprises. They wanted love. Not for me, said Thurston. Thurston wanted sex, and he wanted eagerness about the sex. So one day when he was at the gym, he saw this old guy with a very pretty young lady, and when Thurston expressed confusion to his trainer, his trainer explained that the geezer was her sugar daddy and that the young fawn was his sugar baby.
Well, you could barely keep Thurston on a lat-press machine after that. He dashed home and did some Googling and found SeekingArrangement.com, a site built for wealthy (to varying degrees) men who are seeking a formal (to varying degrees) arrangement for sex and (to varying degrees) companionship with someone who in turn is looking for cash and prizes without any drama. Drama, according to Thurston, includes taking your time to decide whether you want to have sex, having any motive beyond the one you stipulated up front (which was greed), and a presumption that you will be courted. No, sir, Thurston's courting days are over.
Sugar dating is the oldest dynamic around: Rich person contracts poorer but younger/hotter person into some combination of obligations that includes but is only rarely limited to straight-up sex. As long as people have had money and other people have wanted money, this has been a thing. But technology has affected this mini-economy twofold: First, as with any Etsy shop, anyone with a good to sell can now easily intersect with someone who wants this good; and second, it has created a culture of righteous entitlement, in which a fringe thing feels mainstream when you find enough people who participate in it.
SeekingArrangement is just one of several sugar-dating sites, but a popular one. On all these websites, the splash page features a beautiful young woman, elegant but with sideboob, and either she's overtly dangling a piece of jewelry or she is wearing it. She looks into the camera. Each time, a man, older, nearing silver status, is looking right at her, unable to take his rich, priapic eyes off her. He has the beginnings of male-pattern baldness: baldness that says, “I've lived, I have money, here is a bracelet.” He is about to lean into her neck, maybe take a big old bite out of it, and she hangs back, only for a moment, only to tell us her secret, which is: “Look, I got a bracelet.”
Everyone on SeekingArrangement knows what they're there for, Thurston says. What is so bad about formalizing the arrangement so that we can all just go home happy? And aside from that unpleasantness with that woman who scammed him, all Thurston had to wrestle with, really, was the nagging guilt that maybe this whole sugar-dating thing isn't so okay, particularly since he began before his divorce was even finalized. “I went to church every Sunday. This felt like an ethical dilemma.” But he reminded himself that he was actually helping someone, a poor student, or someone who badly needed the money for, I don't know, medical bills or back taxes or vaping supplies. And that's what it came down to: “The whole concept of a sugar daddy intrigued me, because even if I were dating someone traditionally, I'd give them money anyway.”
In any case, Thurston found no shortage of willing candidates eager to accept his altruism, and he dated a bunch of them at once, feeling like a “kid in a candy store.” Eventually he settled on one very beautiful woman, 28, in real estate, with a Wells Fargo account that he could drop $5,000 into each month. A note on the negotiation, from Thurston: “A lot of women put like $10,000” in their online profiles as their hoped-for monthly stipend, but “you just say ‘I'll give you $3,000’ and they say yes.” But he was still a novice at this, so he offered her $5,000, and she jumped at it. They saw each other for five years.
Thurston got his happy ending, and he never got scammed again. And he knows he got off easy with that woman; there are worse and more humiliating scams in the sugar-dating zip code than just losing a few hundred bucks. Back in October, Manhattan millionaire Paul Aronson, 85—85!—was left tied to his coffee table for twenty hours by 17-year-old twins he met through SeekingArrangement. He was rescued eventually, but while the twins got what they came for, poor Paul never did. In 2013, Google executive Forrest Hayes spent his last hours nodding off on his yacht after the sugar baby he met on the site injected him (willingly) with heroin; he (less willingly) died in front of her. (The sugar baby, Alix Tichelman, pleaded guilty to involuntary manslaughter this spring and was sentenced to six years in jail.)
But those cases are anomalies, for the most part. For the most part, the scamming in sugar dating is mutual.
There was a really famous TV star at the bar of the Manhattan restaurant where I met Kitten Babypuss (not her real name), but not one person was looking at him. Instead, it was Kitten, with her fake fur and her high heels and tight jeans and her elaborately etched glitter makeup, who drew everyone's eyes—a very beautiful Bratz doll. It was Kitten, 23, lip liner slightly darker than her lipstick, lips that I sort of wanted to touch, who made a woman in her forties stare so angrily that her husband forced her to change seats so that her back was to Kitten.
Kitten left home when she was 18 after a fight with her family over a boyfriend, and she wasn't welcome back, not even after the relationship ended. She wound up in a program for homeless youth and lived in a shelter. Most of the girls there weren't pretty like her, and they'd make fun of her, saying, “What are you doing here, princess?” She never felt safe.
One day, she saw a Dr. Phil segment about sugar dating. “They were talking shit about it, saying it wasn't a good thing to do.” But Kitten saw it differently; she saw a way out. “I wondered how would my life be different if rather than leave a relationship with nothing, I left with more than I came into it with.” She signed up with SeekingArrangement before she even left the shelter.
Kitten was in it to pay for her education. She wants to become a choreographer, and the money has been really helpful. Kitten says that it isn't always about sex: There were some nebbishy men (and some women; she's sugar-dated both) who just wanted companionship. “A lot of them are very lonely and they don't have time to go through traditional dating because they're so successful. And they really don't have time to woo a woman or to like, you know, answer your phone calls.”
Kitten doesn't like to think of it as getting paid for sex—she thinks of the sex as just something that happens naturally when two people spend time together. And she thinks of the money as a contribution a real boyfriend would make, just more. Sometimes she gets a wad of money to go buy some clothing. Other times, it's concert tickets with backstage passes. Prada sunglasses, Jimmy Choos, Armani clothing, her Honda Civic...
But the world can be a judgmental place. Kitten was teaching dance to kids for a while, and then one of the parents caught wind of what she did on the side, and suddenly there was no room for Kitten in the next season's teaching roster. The woman who had protested against her, according to Kitten, had escaped her abusive husband by secretly setting aside extra money until she could afford to leave him. “And I was like, ‘You're not doing anything different than I'm doing, except you're stealing.’ ” Which, sure, those two things seem exactly the same.
A thing people like to do in the sugar realm, when they're being defensive, is they like to tell you how they're doing just another version of what you're doing. “I bet you and your husband have a mutually beneficial relationship,” Kitten said to me at one point. I told her that wasn't really true. We just loved each other and made it work. We're also both journalists, me and my husband, which is to say that we've been bringing each other down financially and “beneficially” since the day we met. Okay, says Kitten, but what she means is that this is really no different from what a stay-at-home mom does with her working husband: You earn the money and I'll do this other thing we need. The world is built on compromise and negotiation, and life is a series of small humiliations. All these arguments are in service of telling me that it's only our ingrained puritanism that brings us to judge formalized arrangements like this.
Before we parted ways and the woman at the next table was left to return to her resting blood pressure, Kitten showed me the SeekingArrangement app on her phone, all the messages that constantly come in from potential suitors. Some are cut-and-paste jobs saying, “I am interested in meeting a smart, classy woman interested in pushing her boundaries” (read: have threesomes). Most of them, though, simply read “$500?” or “$1,000?” and that's it.
“Look at me,” says Kitten. I do. We all do. “I'm going to be used for my body. I might as well get something from it.”
Scrooge McFuck (not his real name) does not want a chub or an older girl (say, over 30), and he does not want “a black,” and yes, maybe you'll think he's a jerk, but he wants what he wants, and what is so wrong with that? Scrooge could probably have any woman he wants—he's wealthy and single and a TV producer in Las Vegas—and so it's hard to understand why he doesn't just go out there and find someone in a more traditional way.
Until he explains it. See, Scrooge has a Weird Sex Thing he likes, and he finds it hard to bring it up. “I'm not going into detail here”—and he never does, and we will all die not knowing, all of us except a few lucky ladies—“but there are certain things that I enjoy about sex, certain things, and it's difficult to tell the typical date about those things, so I never get past the first date.”
When someone is part of an arrangement, though, they are more understanding about your Weird Sex Thing, Scrooge explains, because they are evaluating a deal; they are not assessing your morality. You can even put it out on the table before the first date. And if she says no, she's not for you. Her loss!
(And here I must confess that I've become obsessed to the point of being unhinged over trying to figure out what sex act Scrooge could possibly want that is so horrible. Is it something plain and regular, like anal? Maybe he wants to wear some lingerie? Does he want to punch her in the stomach while he sucks on a pacifier? Does he need her in a clown suit as he takes a dump on her clown nose? I'll be doing the dishes and it will come to me, these unbidden thoughts that are nonetheless relentless. Often in the past few months, my first thought upon waking up is a new possibility for Scrooge. “Maybe he wants to wear a saddle and be hit with a riding crop while he recites Whitman,” I will tell my husband. “Can I have coffee before we discuss this?” he will answer.)
There was some trial and error in trying to find the right girl, but eventually Scrooge found a 22-year-old whom he was able to take to Pink concerts and to plays and to movies before taking her up to his hotel or apartment to conduct the Weird Sex Thing he needs so badly that he cannot even wait till a third date before asking for it. He gives her roughly $500 each time they see each other, sometimes more, sometimes less, depending on congestion pricing.
Now, are you ready for something sweet? He could see himself marrying her! And this, he says, is what makes sugar dating different from prostitution. “I don't have an extensive track record with escorts, prostitutes, or hookers,” says Scrooge. “But I've done it a couple of times in foreign countries. And it's just the biggest turnoff you've ever seen. It's like all business. They don't smile.” With sugar babies, no one's on the clock. There's hugging and kissing, laughing and talking.
With sugar babies, he says, it's almost like a real person who actually loves you.
Tigress St. Fawn (not her real name) was always attracted to older guys, even when she was an undergrad. The guys at college in Boston just didn't do it for her. If she's honest, it was her dad's friends she was always attracted to. (Don't get her wrong, though: “I have a really healthy relationship with my dad; he's one of my best friends.”) Before graduating, she heard about sugar dating, and the minute she did, she immediately booked herself five dates in one week, as a sort of immersive experience, in hopes of getting the full breadth of all it had to offer. Here's how the week went.
Monday: She met the guy at The Charles Hotel and went back to his place. She gave him a blow job, and then she fell asleep for two hours. He woke her up to drive her home and said, “ ‘Oh, I have like $500. Is that okay?’ And I'm like, ‘Oh yeah. Yes, that's fine. Yeah, that's great. Thank you.’ He's like, ‘Okay. Here.’ Like, ‘I'll talk to you soon.’ ”
Tuesday: She met another guy at the local seafood shack for shrimp and margaritas. They went back to her place, and they both tried on her clothes and she gave him a blow job. He left her $400. He's married, but something something something—Tigress never got the full story. She still sees this guy.
Wednesday: This guy was really old, maybe 75. After sushi and a Viagra, they went to his house. He lay down on an ottoman and asked her to get on top. Eventually he had convulsions that were not unlike an orgasm, but something was off. He told her to leave. The next day he texted her from the hospital and told her he was breaking it off because she was “too crazy” for him in bed. $500.
Keep in mind it's only Wednesday.
Thursday: She went out with a scientist in his late fifties whose wife had a medical condition that prevented her from having sex or something else that is obviously completely made up. They didn't get around to the sex stuff until date two, but when they did, he asked for her to tell him incestuous fantasies while they did it—sisters, uncles, whatever. $500, boom.
Friday: She met a European scientist who asked her to accompany him to a conference in New Orleans for $5,000 for a week. She said yes, because that sounded like a vacation compared with the week she'd just had.
Now, Tigress is an MFA candidate; she showed me her chapbook, which is equal parts poetry and erotica. Her parents know about the men, and they don't love it, but, well, are they paying all of her tuition? They are not. If you ask her if this is prostitution—I never once did with the women I interviewed; every time, they brought it up—she'll say the question is moot.
“I'm kind of pragmatic about the whole thing,” she says. She looks across the table at me, the dummy who had to reschedule on her twice because of all the work I juggle, who has spent far more time and energy writing this story than a commensurate amount of blow jobs would require.
For Tigress, the question is not whether she's a prostitute. It's whether the rest of us are idiots.
John (not his real name) wanted all New York City had to offer when he left his conservative parents in Connecticut for school. They couldn't accept that he was gay, so good riddance to them and their money. But Manhattan is expensive, and he really wanted to live the life, so he and his best friend—a young woman also newly arrived at college—set out to see how they'd fare if they tried SeekingArrangement.
At 20, John has had two sugar daddies with formal long-term arrangements, and a couple of one-off dates where he just met the guys and got dinner and a show. He refused to have sex with any of them immediately; he wanted the guys to have to work for it. But they wouldn't, because that's not how this works, so he got dumped. Finally he found a guy who was married to a woman and kept a pied-à-terre for his sugar-baby dalliances. He was selfish, according to John, and they never went anywhere—the guy just wanted sex.
The second guy was better, and they had a good run together. John was never comfortable with the implications of a cash exchange. Instead, he took gifts: a Marc Jacobs watch, some suits from Burberry. “I would rather have the experiences and stuff,” he says. “Tangible things instead of just ‘Here's some cash.’ That's tacky to me, to be completely honest. It's totally tacky.”
Eventually the guy broke up with John. He wanted to have threesomes, and John didn't, and the way the guy acted—angry, entitled tantrums about “didn't I buy you a new computer”—showed John exactly what was going on here. John had seen this before. The first guy didn't want to use protection, and he seemed to get turned on trying to get John to relent, then was outraged when John refused. John got out. Now he works the front desk at a health club.
Sometimes John misses sugar dating. Without it, he'd never have seen The Book of Mormon on Broadway, which he highly recommends. And there was the traveling, too. He got a glimpse of a life he couldn't afford. But something in him knew that there were things he shouldn't just be giving away.
“We went to Naples,” he told me. “It's sooo beautiful. Have you ever been?” No, I told him, I'd never been to Italy. He furrowed his brow and corrected me.
“It's right near Sarasota.”
Rich (not his real name) and Ilene (nor hers) walk into maybe the fanciest restaurant in this small midwestern city, which is saying nothing.
I didn't expect who I've found. I'm naive in general, but at this point in the story, I'm so much less naive than I've ever been. I traveled for six hours to be here, and there's not even a measly garter belt or gross double entendre in sight. Instead, I get Rich and Ilene, both smiley, she with her freckles and dimples, he with his goofy laugh.
She's 20, a registered nurse who ran off from her controlling parents. He's 33, an academic who just couldn't find the right girl. She saw that same Dr. Phil episode with the sugar babies—“It was just slut shaming,” she says—and she saw the potential for something better. She needed to get through nursing school. She needed to not be in debt for the rest of her life.
(Now, here it would be fair to wonder: Just how much does an academic earn? I met sugar daddies who make $100,000. I met ones who earn more than a million. To imagine that this is for rich people is to have missed the point; any amount of money is more money than some people have. Megalomania is not only for the one percent.)
Rich was trying to meet people, putting himself out there, open to setups, but who are you going to date? A student? He tried OkCupid, Match, all of it. But this town, so small that the university Wi-Fi network works in every corner of it, is not exactly flooded with eligible women. His last relationship was long-distance; she had a high-powered career, and eventually he realized he needed to be the one calling the shots.
Rich and Ilene met and had sex at his apartment that very night. But their arrangement seems more like a father-daughter relationship than anything else. She needs an interview outfit? They'll go shopping for it together, and of course he'll buy it. I ask if she realizes that one day she won't be 20, and one day she'll want to buy something without having to ask for it. She shrugs and says yes. He sighs. He didn't realize they were going to be this honest with me.
Not all sugar dating is pathological, but psychologists will tell you that this is the point of it all: that yes, there are people who just want to date someone and not have to meet their mother or answer their needy text messages, but most of them are in it for the power—not just the choices that the power enables, but the aphrodisiac of the power itself.
One specialist told me that most of these people want to be saviors, but they also want to humiliate. It's a common dynamic to suss out the sugar baby's boundaries—threesomes, say, or anal, whatever it is that pushes her beyond her moral code or value system—and then make her an offer that gets her to do it anyway: There's the power, and the altruism. It's not just that John's sugar daddy wanted to have unprotected sex with him. He wanted to make John do something he didn't want to do, and then have the quick cleanup of his conscience by saying, “But I'm helping the poor kid!”
Rich and Ilene are sweet together, truly, holding hands, sharing their food, in sync, and their arrangement now is for good. Not long after our meal together, he proposed, and Ilene is relieved. When people ask, they just say they met online, that the age difference “is what it is.” And that will be that.
Back at dinner, I take my glasses off and set them on the table and rub the bridge of my nose. It's been a long time since I began this story, and I have been exposed to no small amount of sociopathy, delusion, denial, and misogyny in the reporting of it. So many women telling me they want their “Pretty Woman moment.” So many men telling me how kind they are to be supporting, even mentoring, “these girls.”
And in exchange “these girls” think they're getting what they want. But you can't get what you want in this world without a scam, without thinking you are the grifter and not the mark. Kitten believes she is gaming the system, profiting off her body instead of being used for it, but she's not making as much as she could if she were a better negotiator. Tigress thinks she's doing the smallest amount of work for the most amount of money, but if you talk to her, there is something off there, something not right in her bragging and eagerness. John's sugar daddy, who bought the suits and the domestic plane tickets, thought he was the one in control, but it was John who had what the sugar daddy wanted and wouldn't give it to him. Everyone here is on the hustle, and everyone here thinks they're winning. And so what's so wrong with that? Who exactly is getting hurt?
That, my friends, is the scam, here at the intersection of greed and loneliness and insecurity and the basic human need for survival. You can tell yourself whatever story you want, and eventually you'll forget you're telling a story and you'll find yourself in the parking lot of a Pizzeria Uno getting sucked off by someone who thinks she's getting the better end of the deal. And the worst part is, you'll think you're helping her. And she'll give you that blow job, all the while wondering how she could get so lucky, how you could be so dumb. Everyone gets what they want. And, sure, what's so wrong with that?
