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(He liked that hotel, she said, because you can book a room online and then check in at an unmanned electronic kiosk.) “It was very natural and it felt like a normal hookup, except he gave me money after,” she said. She went back onto the site and soon received a message from a man who said his name was Jay and that he was an investment banker at Bain.

“If you are interested in being spoiled, I have a very generous allowance and it would be a once a week thing,” he wrote to her, according to Ms. He included a mobile number and requested that they speak.

Sugar daddies (and some sugar mommies) pay monthly fees of a month, which allows them unlimited access to the profiles of sugar babies, who join the website for free.

(“Diamond” memberships for sugar daddies cost 0 per month and provide sugar parents with search engine optimization and top-of-page promotion for their profiles.) The website is illustrated by stock photos of white women, sometimes carrying shopping bags and often in formal gowns and diamonds, fawning over white men with business-trip suitcases and carefully groomed 5 o’clock stubble.

Chandler Fowles knew it wouldn’t be simple to move from Mystic, Conn., to New York City last year. Her degree in art history and fine arts from Eastern Connecticut State University wasn’t helping her land any job worth sticking around for. She and her mother weren’t speaking at all after a particularly bad argument. The cost of living (and partying) was more than she could manage, along with her ,000 in college student loan debt.

When you are 24 years old, jobless, boyfriend-less and in a fight with your mom, moving to one of the most glamorous, ballyhooed cities in the world can seem like a good idea. Last winter, a friend told her about the concept of “sugar-dating”: a “sugar baby” (most often a woman or a gay man) connecting with a “sugar daddy” (a man) in a relationship that offers financial support in exchange for companionship and possibly sex.

She signed up on Seeking Arrangement.com, a website that helps people interested in monetized dating find each other.

They were going to meet that very night, but something — his jet lag from a trip to London, or maybe it was her menstrual cycle — got in the way. Fowles and Ron were back on the phone, planning a rendezvous.

He asked her if she had a friend to bring along, whom he would pay the same amount.

The terms of service, he said, prohibit transactions for sex; the site simply seeks to bring the role that money plays in mating out in the open.

“We want to drive people to talk honestly on the first date about who they are and what they expect to gain from a relationship, just like you discuss in any business relationship and any business arrangement,” he said.

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