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Harvard dating scene

"I only go out with girls 25 and under," says Jack, whose thick head of white hair and bushy eyebrows form a halo around a red, flushed face.

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She planned on spending the day with a man she had met online, but not in person.An increasing number, according to the owners of websites that broker such hook-ups, have taken to the web in search of online suitors or wealthy benefactors who, in exchange for sex, companionship, or both, might help with the bills.The past few years have taken an especially brutal toll on the plans and expectations of 20-somethings.Rich guys well past their prime have been plunking down money for thousands of years in search of a tryst or something more with women half their age -- and women, willingly or not, have made themselves available.With the whole process going digital, women passing through a system of higher education that fosters indebtedness are using the anonymity of the web to sell their wares and pay down their college loans."I just wanted to get out of that situation as safely as possible, pay off my debt, and move on." While she and her host hadn't agreed to a set amount of money, on the drive back to the train station in Greenwich he handed her $350 in cash. I just did what needed to be done." And she's still doing what needs to be done.

She pocketed the envelope, seeing it as decent money for half a day's work. I mean, I had just gotten money for having sex," says Taylor, who never heard from the guy in Greenwich again. With tuition due in September to pay for her last semester of college, Taylor's back on the hunt for other, more lucrative online hookups. "It's a very expensive job," says Jack, a 70-year-old sugar daddy, who describes himself as a "humanitarian" interested in helping young women in financial need.

He typically forks over about $500 a night -- and that's not including lavish dinners at Daniel or shopping excursions on Madison Avenue.

"Unlike a traditional escort service, I was surprised to find such an educated, smart population," says Jack, during cocktail hour recently at the Ritz-Carlton in Manhattan.

But after taking a big hit in the financial crisis and being forced to downsize, Jack says he had to part ways with his private jet due to what he describes as "reduced circumstances." On the site, he lists his annual income as $1 million and his net worth as something between $50 and $100 million.

While sugar babies can create profiles on Seeking Arrangement free of charge and a regular sugar daddy membership costs $50 each month, Jack pays $2,400 a year to belong to the Diamond Club.

She and her host ended up in his bedroom, where he peeled off her bikini.