Desperately Seeking Sugar Daddies
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.
Regardless, I decided to stay for a drink, as he seemed harmless enough. Within minutes, however, another lie revealed itself. Darrell was speaking about a previous relationship with a much younger woman whose flat he had paid for in Rome, where he’d visited her.
“How long ago was that?,” I asked.
“Ten years ago, when I was in my late 40s.”
By the time Darrell laid out his offer, I couldn’t take him seriously. “There are two options here,” he said. “I can give you an allowance, or I can employ you at my company.”
“Interesting,” I said, but I was entirely skeptical. When Darrell and I parted ways, I knew I would never see him again.
Several weeks into my search, my experiences had been motley. Dating through Seeking Arrangement didn’t seem so different from normal dating—you meet all kinds of people, some of them inevitably loony, and see whether or not you connect. And like the regular dating world, it was starting to feel a bit daunting, as I hadn’t found anything close to what I was looking for. I was willing to forgo looks, but I couldn’t force myself to be with anyone I disliked or mistrusted.
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.
