This article, by a would-be writer, appeared in Vanity Fair recently.
Vanity Fair: ... I had become a member a few weeks earlier, partly as a social experiment and partly out of genuine desperation. I was frustrated with my job, which offered little upward mobility, and was thinking about quitting it to pursue my goal of becoming a full-time freelance writer. Holding me back were my lack of savings and my fear of sacrificing a regular paycheck. If I had a hefty allowance from a generous benefactor, though, I figured that I could take the leap comfortably.
... The site, which launched in 2006, has about 420,000 members, of which roughly one-third are sugar daddies and two-thirds are sugar babies (sugar mommies account for less than one percent). While sugar daddies pay $49.95 per month for a premium membership (or $1,200 a month for Diamond Club certification, which requires verification of one’s net worth through tax-return data), as a sugar baby I was able to join for free. I uploaded two photos and listed some general information about myself, and I stated “open, amount negotiable” in the space that asks what you’re looking for. (Seeking Arrangement skirts the issue of prostitution by promoting the exchange of “intimacy and companionship” for “gifts.”) I took a deep breath and posted my profile, determined to focus on New York–based single men claiming to be worth at least $10 million.
... When Charlie—divorced, late 50s, worth about $50 million—asked to meet me, I tried to remain hopeful. I sauntered into the Mercer Hotel in jeans and a gray cardigan one frigid Sunday morning, scouring the crowd for a tall, gray-haired man. He spotted me first and tapped me on the shoulder.
“Here you go—just a token,” Charlie said, extending his hand.
I examined my gift—an iPod—and said, “Thank you,” determining to be extra pleasant during brunch.
We both ordered eggs, and by the time our food arrived I had grown to like Charlie. For starters, he provided an earnest explanation for joining Seeking Arrangement.
“I can’t separate the fact that I have resources from who I am,” he said. “It’s part of me. And it’s something I have to offer twentysomethings.”
“I completely agree.”
“I married young, you know. And I remained married for nearly 30 years while I was raising my kids.”
“How old are they?”
He chuckled before admitting, “It’s kind of weird. They’re your age.”
“It’s not weird at all,” I said.
Charlie turned to Seeking Arrangement, he explained, because most of the women he had been meeting wanted to settle down. “I don’t want another family,” he said.
“I promise you I’m not in the market for one,” I told him, and then asked, “Have you ever done this before?”
“I’ve never been in one of these relationships, exactly. But I’ve certainly been generous with previous girlfriends. And since joining the site, I’ve been on a few coffee dates. Pretty positive experiences, actually. I met an editor for a fashion periodical, a translator for the U.N., and a girl whose dad”—he stopped to laugh—“whose biological dad had just cut her off. The only negative experience I had was with a girl who was dating a hedge-funder. She said he had given her her nose and her Birkin bag, but that she needed cash. A bit mercenary for my taste.”
Here is a segment that features the founder: