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He typically forks over about 0 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.
He said he lives next door in a penthouse apartment overlooking Central Park South and pays ,000 a month in rent.
In his profile on Seeking Arrangement, Jack describes himself as a 67-year-old with a bachelor's degree. C., native says he founded four financial services companies.
She and her host ended up in his bedroom, where he peeled off her bikini.
Once in Greenwich, a man who appeared significantly older than his advertised age of 42 greeted Taylor at the train station and then drove her to the largest house she had ever seen.
While he summered on Martha's Vineyard, she'd likely pass another July and August working retail in Times Square. ("Taylor" is the pseudonym she uses with men she meets online.
Neither she nor any of the other women interviewed for this article permitted their real names be used.) In her profile on the site, Taylor describes herself as "a full-time college student studying psychology and looking to meet someone to help pay the bills." Photos on the site show her in revealing outfits, a mane of caramel-colored hair framing her face.
"Most of these young women have debt from school," says Jack, who finds most young women also carry an average of ,000 in credit-card debt.
"I guess I like the college girls more because I think of their student debt as good debt. Wade, who started Seeking Arrangement back in 2006, can easily identify with the Jacks of the world.