The ‘sugar daddies’ and ‘sugar babies’ at deny they’re engaging in prostitution. At the very least, says Ruth Padawer, their relationships are more complicated than that.

At first glance, the website Seeking­ seems like any other dating site. Most of the men are looking for fit, sexy women, and most of the women want nice guys who can make them smile and laugh. But if eHarmony and are chatty social mixers, Seeking Arrangement is a down-and-dirty marketplace where older moneyed men and cute young women engage in brutally frank transactions. They’re not searching for longtime soul mates; they want no-strings-attached “arrangements” that trade in society’s most valued currencies: wealth, youth, and beauty. In the cheesy lexicon of the site, they are “sugar daddies” and “sugar babies.”

There’s the 18-year-old from France asking for $5,000 to $10,000 a month from “a mentor who can provide me with the finer things in life and keep me happy!” And the 49-year-old investor from upstate New York willing to pay $5,000 a month for a “daytime playmate” for “intense connection without commitment.” Critics say the site is at best a convenience store for adulterers and at worst a virtual brothel, but Brandon Wade, Seeking Arrangement’s 38-year-old founder, is unperturbed by the criticism. “We stress relationships that are mutually beneficial,” he says. “We ask people to really think about what they want in a relationship and what they have to offer. That kind of upfront honesty is a good basis for any relationship.”

The site now claims more than 300,000 registered members, only one-fifth as many as mainstream, but still a remarkable number. Sugar babies outnumber daddies 10-to-1, Wade says, providing what one sugar daddy called “the best fishing hole I ever fished in.”

This abundance of possibility is part of what the site is selling. Some of these men are digging deep into their pockets to pay for the illusion that, despite their receding hairlines and wattled skin, they’re still enchanting enough to have their choice of pretty young women. But the relationships that develop between the “daddies” and the “babies” who meet on the site often turn out to be more complicated than even the members themselves expect.

Consider B.K., a fit finance executive in his early 40s who, last October, began “dating” a 20-year-old engineering major at a college 90 minutes from his house. Like nearly half the sugar daddies on Seeking Arrangement, B.K. is married. (Neither B.K. nor any other user of the site would allow his or her full name to be published.) B.K. and his wife opted against separation, for the sake of the kids, and for now, they have a policy—at least in his mind—of don’t ask, don’t tell. Between pangs of guilt about cheating, B.K. views his secret dallying as a safety valve, letting him feel desired so he can return home and appreciate the many things he loves about his wife, even if they don’t include giving him the attention he wants.

And so, nearly each week, B.K. gets together with Lola, the young woman he met on the site, for a meal or a gym workout and a few hours at a hotel outside the Western city where he lives. Their visits are generally no longer than four or five hours because Lola, a senior, has a full course load and also works 40 hours a week in low-wage jobs as a lab assistant and housecleaner. With no money from her parents, she was frank in her Seeking Arrangement profile, saying she needed “immediate financial assistance.” In B.K., she gets that in the form of $100 or $150 stuffed in her bag each time they meet. He feels good about helping her with her tuition, encouraging her studies, and romancing her, albeit in hotel rooms. Most of all, he’s grateful that she doesn’t want a commitment. At least he was at first.

“It would be nice not to have the money involved, because you always wonder: Would she still want to be with me even without the money? Does the money make me more attractive than I really am?”
About 30 percent of arrangements on the site involve the daddy paying an “allowance,” usually a thousand or two a month, though the site claims some reach $10,000. The rest provide the baby with incidental cash, shopping sprees, gifts, travel, or the fleeting illusion that theirs is a high-end life.

Many women on the site, like Lola, are in their 20s, though plenty of others are in their 30s, 40s, and 50s. A surprising number of babies claim on the blog that they don’t need the money at all, either because they have decent-paying jobs or bottomless credit cards from their parents. What appeals to them, they say, are the expensive gifts—“I just LOVE being spoiled,” gushed one 19-year-old woman—because those gifts make them feel valued.

Other women on the site openly prefer the cash, especially for tuition. In fact, Seeking Arrangement pays to have its ads pop up on search engines whenever someone types in “tuition help,” “college support,” or “help with rent.” Lola was one of many to stumble on to the site that way, when—behind on her rent and tuition and down to one meal a day—she Googled “student loan.”

Her first sugar daddy, a man in his early 50s, turned out to be a terrible kisser and too dominating in bed. “I had to grit my teeth every time we met,” she says. In four visits, she earned $550, then dropped him. A month later, she connected with another sugar daddy, a man in his late 50s who lived in Louisiana. The only thing he wanted, he told her, was that she do well in school. He insisted she send her transcript, and once satisfied, he sent her nearly $500 a month. Though they never met, never even talked on the phone, he wrote her long letters by hand encouraging her studies and advising her on finances.

Six months later, though, when the man in Louisiana had to cut back on expenses, Lola began looking for a new source of extra income. Last October, Lola and B.K. had their first date. “At first, it was a job, then it became a pleasant job, and then it was getting together with a friend,” she later told me. “With him, I don’t feel like a prostitute, though maybe I am. It’s not just the sex with us. We care about each other, we talk, there’s a connection, not just business.”

Brandon Wade got the idea for his site from his own dissatisfying love life as an MIT student and then as a well-off but awkward tech executive. “It was difficult to advertise the assets I had compared to hundreds of thousands of guys who had better looks or better pickup lines,” says Wade, who adopted a fake surname when he started Seeking Arrangement. His legal name is Brandon Wey.

Wey unveiled in 2006 and aimed to keep the site well stocked for his wealthy customers. Babies can join free, while daddies pay $44.95 a month—and an optional $5 to ensure that the site’s name doesn’t show up on credit-card statements. For another $1,200 a year, a sugar daddy can become a Diamond Club member, with his income and net worth verified and his profile featured at the top of the home page.

Whether sugar relationships amount to prostitution is hotly debated among the site’s members. Many women who post on the blog go to considerable effort to distinguish between “sugar” and prostitution. (Legally, at least, they are right; since the 1970s, courts have ruled that as long as the woman is paid for some service besides sex—housecleaning, companionship—the arrangement is not the equivalent of prostitution.) They say being a sugar baby is no more an occupation than dating is, especially when the goal of dating is to find a rich boyfriend or a wealthy husband. They routinely turn down creeps interested in nothing but sex.

Relationships between rich men and kept women have been around for a very long time, of course, but the Internet makes hunting for such arrangements easier. One sugar daddy whose screen name is Sam has an almost mathematical approach to assessing romantic relationships. The single 39-year-old entrepreneur has even computed relative costs and concluded that mistresses are most expensive by the hour; wives by the year; girlfriends are cheapest all around. Even so, he’s found the arrangement that suits him best is a monogamous business-associate-with-benefits deal in which he pursues an entrepreneurial project with a young, beautiful, intelligent woman. At the outset of these arrangements, he asks the woman to sign a contract in which he commits to paying her a stipend of at least $5,000 a month for the duration of their relationship. If the woman decides to quit sleeping with him at any point, the stipend continues regardless. But because the contract always has a fixed end point, there’s usually no breakup, no rejection, no bruised ego. She’s not dumping him; the gig’s just over.

From the start of B.K.’s relationship with Lola, Lola was clear that her heart lay elsewhere. Her boyfriend of four years lives 1,000 miles away, and though they see each other only a few times a year, Lola maintains that she is deeply in love with him. When B.K. asked Lola what gift she wanted for Christmas, she demurred, but when pressed, she asked if he would pay for plane fare to visit her boyfriend. B.K. said yes—and felt great about it. “Isn’t that what love is?” he told me later. “It’s not about trying to own someone.”

But while Lola was gone, B.K. sent her e-mail and text messages virtually every day and suffered when he heard nothing back. Pining, he began trolling the site, window-shopping, and noticed Lola had logged on. He feared that she was looking to replace him. “I was like, What the hell is this?” He e-mailed her, asking why she was on the site, but got no answer. “Maybe I’m the needy one,” he mused.

When Lola returned, she told B.K. she’d been out of touch because her cell phone battery died. She reassured him that she wanted to keep seeing him. But she also reminded him that she had several looming deadlines at school and at the lab where she worked. Their visits dwindled to every other week. Through Seeking Arrangement, B.K. began communicating with a new potential sugar baby. He even met her for coffee and suggested he could pay her $1,500 a month. She objected that she was worth much more.

The next time B.K. met with Lola was after an extended lull, and he asked more about her boyfriend than he ever had before. Speaking tenderly, Lola told him she loved her boyfriend and that she hoped he would propose after she graduated later in the year. Once engaged, she added, she would stop being a sugar baby.

B.K. felt devastated. Days later, though, his new prospect e-mailed him after weeks of silence, and he arranged to meet her at a local bar.

He was waiting in a back booth, he told me, when she showed up in a tight, low-cut blouse and scooted up next to him, purring that she’d reconsidered his offer: $1,500 a month would be just fine.

© 2009 by Ruth Padawer. From The New York Times Magazine. All rights reserved.