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Since I was still a bit hesitant about how far I’d be willing to take my experiment, I signed up using the pseudonym Annabelle Walker.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).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.Hank requested sparkling water, explaining, “I’m high on life.” I wanted to tell him, “Abstemious people don’t impress me,” but instead I smiled and encouraged him to order for both of us. I was beginning to understand his relationship philosophy: renting a girlfriend is a safer alternative to investing in a wife.

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?The first thing I noticed when I met Darrell for cocktails at the So Ho Grand Hotel was that his appearance did not match what his profile had advertised.He’d said he had brown hair, but he was almost completely bald; his body type was more teapot than “athletic”; and he was several inches shorter than he had claimed.Unsurprisingly, Hank made a move on me, and I kissed him for a split second before withdrawing abruptly. I sensed that he wanted a puppet more than a girlfriend, and no amount of gifts or pampering could compensate for having to deal with such a controlling person.So I scrambled to the front door—thankfully, it was unlocked—and bid Hank good riddance.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.Before we sat down, Hank gave me elevator eyes and said, “Good. Even with a pre-nup, though, you’re at risk.”“Right,” I said.I need a tall, blonde girlfriend.”When the waiter arrived, I ordered a very necessary glass of Sauvignon Blanc. I allowed Hank to feed me a piece of meat and chewed thoroughly. We were at Megu, a pricey Japanese restaurant in Midtown Manhattan, eating perfectly cooked Kobe beef.My companion, a wealthy finance type, was telling me all about himself and posing questions that suggested he was interested in me.

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