The Times magazine has a long piece about SeekingArrangement.com, a web site that helps "sugar babies" find rich "sugar daddies" :-) On the site there are 10 babies for every daddy.
I would say that a large number of financially successful guys I have known have analyzed the dating situation (usually over a few drinks) and come to the same conclusions as the users and creator of the site. (See further down the excerpt, and especially the guy called Sam.) I don't personally know very many women who have analyzed it from the other side and come to the sugar baby perspective (or at least will admit to it), but there are obviously lots out there. See the sugar daddy blog for hundreds of comments from sugar babies.
For the Asian version of all this, see Enjo kosai, or "compensated dating" in Japanese (also here and here).
NYTimes: AT FIRST GLANCE, the Web site SeekingArrangement.com 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 or Match.com is a chatty social mixer, 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 and chief executive, is unperturbed by the criticism. “We stress relationships that are mutually beneficial,” he says. ...
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, easy life. “I get flown to whatever city I want,” wrote a North Carolina college student, who goes by the name gurlnextdoor on the site’s blog, a mix between an online support group and a kaffeeklatsch. “He pays for it, takes me shopping, we talk, laugh, go out to eat and do whatever we want to do for our days together. . . . I don’t bring up mundane problems about my home life, and he does the same. . . . If I wanted someone to talk to about my life problems, I’d get a boyfriend or a therapist.”
...In fact, Seeking Arrangement pays to have its ads pop up on search engines whenever someone types in “student loan,” “tuition help,” “college support” or “help with rent.” Lola was one of many to stumble on the site that way, when — behind on her rent and tuition and down to one meal a day — she Googled “student loan.” What popped up was hardly what she expected, but she was willing to try almost anything to stay in school.
...Whether sugar relationships amount to prostitution is hotly debated among the site’s members. “Let’s get real here,” wrote GoldenGate on the blog. “I’m with a guy who’s old enough to be my dad, short and balding. Not to mention his other shortcomings, ahem. But he gives me a great big fat allowance every month. If that wasn’t there, we wouldn’t be together.”
Others on the blog were shocked, saying they could never be with a man, even a rich one, if they weren’t somehow attracted to him. Indeed, most 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. ...
Some sugar babies also insist that wives who stay in miserable marriages for an American Express black card, mansion or country-club membership are more like prostitutes than they are. And yet the blatant financial transactions leave many uneasy.
...a 22-year-old named Mercedes told me, “I don’t see how people can view this as exploitation.” Mercedes is a junior who pays her own tuition at a Georgia university. She has had six sugar daddies in the past year to supplement her wages busing tables and washing dishes at a bar. “I could go out and work three jobs and still go to school and probably make decent grades, but is that really what I want to do? I make more money this way, and I have a lot more fun because I get to go out to concerts, go shopping, see movies and make money off of it. If instead of this I was just dating a rich guy, it’d be almost the same thing, and society wouldn’t look down on that. You know with a sugar daddy that they’re spending a lot of money on you and they clearly want something in return, but is that really any different than how it is with a boyfriend?”
BRANDON WEY GOT THE IDEA for the site from his own dissatisfying love life as an M.I.T. student and then as a well-off but awkward tech executive. Traditional dating Web sites were no help. “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 Wey, now married to a woman 13 years younger than he is, whom he met before the site went live. “I needed to find a way to put myself at the front of the line.”
One sugar daddy whose screen name is Sam has tried long-term girlfriends, mistresses, prostitutes and a brief marriage. ... Sam’s profile on Seeking Arrangement is audacious. He advertises for a woman who is “drop-dead beautiful, sexy, fun and elegantly mannered in a fancy setting. She must turn heads . . . and make me the envy of the crowd.” ... When I asked to chat in person, Sam suggested meeting at CORE, a private Manhattan club where membership is by invitation only and costs $65,000 the first year and where Sam’s assent was required before I could be admitted. Sitting alone at a long conference table in a room set aside for him, he looked utterly unremarkable, a man of average height with a buzz cut and an aloof air. But once Sam got talking, he became affable and witty, especially as he described his unorthodox history with women. He started college when most kids his age were still in middle school. “When you go to college at that age, you’re pretty undatable,” he said. “I was somewhere between a curiosity, a mascot and a friend. I tutored freshman physics and calculus so I could at least be near women. Of course, all they’d do is talk about their boyfriends.”
He has an almost mathematical approach to assessing relationships, and once even computed the costs for a girlfriend, mistress, prostitute and wife — mistresses turn out to be most expensive by the hour; wives, by the year; girlfriends are cheapest all around. But he’s not as calculating as he seems. In fact, he concluded there’s little correlation between cost and quality. Still, he is relentlessly searching for an algorithm that will predict relationships’ success.
Sam is also more determined than most to try separating a sugar baby’s affection and the money she’s paid to provide it. In his arrangements, he says, he establishes a trust in the woman’s name that pays a monthly stipend of at least $5,000 for the length of their contract. If the woman decides to quit sleeping with him at any point, he may quit serving as adviser and pamperer, but the stipend continues regardless. “If I didn’t do that, then it’s like a leash I’m putting on somebody, and that seems really unfair,” he said. “Besides, then I’d never know what the relationship was really about.”
Sam runs these relationships with an explicit business plan, a set budget, measurable goals and quarterly reviews. From the outset, the contract has an end date. It’s a brilliant, if contrived, way to protect his pride. The contract specifies that the romance and sex are to end by the preset date, so there’s no break up, no rejection, no bruised ego. She’s not dumping him; the gig’s just over.