“Sounds fair,” I said. But Hank’s last statement felt somewhat threatening. 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 AmEx card. 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. Curiosity got the best of me, and I consented.

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. Unsurprisingly, Hank made a move on me, and I kissed him for a split second before withdrawing abruptly. He wasn’t unattractive, but I hated him. 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.

The next few people who reached out to me through Seeking Arrangement were not up my alley. One man complained that his disability made it difficult for him to pick up women. 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.

The first thing I noticed when I met Darrell for cocktails at the SoHo 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. This irked me, especially because it was unnecessary. Didn’t he know I was in it for the money?