But back to Megu and my date, whom I’ll call Hank. (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..you 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. Before we sat down, Hank gave me elevator eyes and said, “Good. I need a tall, blonde girlfriend.”

When the waiter arrived, I ordered a very necessary glass of Sauvignon Blanc. 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.

Throughout dinner Hank blabbed ad nauseam, referring to himself as “a citizen of the world” and concluding his autobiographical sketch with: “You really hit the jackpot, you know.”

“I did, didn’t I?,” I said, but it was getting harder and harder to feign enthusiasm. Still, I was committed to seeing this through. “Have you dated anyone else through the site?”