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When he invited me back to his apartment, I felt torn.His promises of expensive shoes and trips to the Caribbean weren’t all that enticing, but I still wanted to fact-check his wealth. Hank led me on a tour of his apartment, which was every bit as luxurious as I’d expected, with floor-to-ceiling views of Manhattan and expensive art on the walls.

It is only natural for males to target cues to fertility such as youth and beauty, and for females to be drawn to displays of resources.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.Another had a fetish for submissives and wanted to pay me $4,500 a month to help him realize his fantasies.An attractive couple wrote me seeking a regular “third.” By the time Darrell, a divorced man in his late 40s worth between $50 million and $100 million, contacted me, I was relieved to hear from a potentially worthy candidate.It also struck me as hypocritical for a man to sign up to be a sugar daddy, put a dollar figure on his girlfriend budget, and then refuse to write checks.

Our bill came, and Hank threw down his black Am Ex card.

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. So what if I had to tap into my inner geisha to secure a patron?

If I had a hefty allowance from a generous benefactor, though, I figured that I could take the leap comfortably. To overcome my reservations about walking the line between dating and prostitution, I told myself that any such concerns were the result of societal conditioning.

The idea of wealthy older people supporting struggling younger ones is nothing revolutionary, after all—look what Peggy Guggenheim did for Jackson Pollock or the Tuohys did for N. The idea that mixing money and mating is inherently bad, I reasoned, was a fallacy based on our collective obsession with moralizing sex.

Then, matter-of-factly, he said, “Whether I met you on the site or at the Standard, you’d cost me at least 10 grand a month.”The site he was referring to was Seeking Arrangement, an online network that pairs people possessing resources (“sugar daddies” and “sugar mommies”) with those, usually much younger, seeking them (“sugar babies”).