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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.

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(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. (Throughout this article, I’ve changed the names of the men I dated to protect their privacy.) Initially, he drew my suspicion with the cocky, typo-ridden message he sent me on Seeking Arrangement: “i think i maybe waht you r looking for; read my profile and if you r interested drop me a line.wont be disappointed.” Then I saw his net worth—$100 million—and the amount he was willing to spend on a girlfriend: $10,000 to $20,000 per month.

That would be enough to cover my living expenses and leave me with thousands in disposable income.

The rest of Hank’s profile, which told me that he was middle-aged, played sports, and worked in finance, was of less interest.

We set up a date and specified what we’d be wearing so that we could recognize each other—a navy-blue baby-doll dress and black tights for me, a striped button-down and a maroon cashmere vest for him.

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 million and 0 million, contacted me, I was relieved to hear from a potentially worthy candidate.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?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.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.

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