I, A Middle-Aged Woman, Went On A Sugar Daddy Dating Website. You’ll Never Believe What Happened Next

I, a middle-aged single woman, have spent the last several years looking for love, a connection, something on dating websites and apps. You name them, I’ve been on them: Bumble, Tinder, Hinge. Over that period I’ve gone on 30 or so blind dates, with pilots and attorneys and one carpenter, most of them somewhere between mildly boring and temporarily entertaining, but nothing has really stuck. So the other night, after I’d deleted another dating app in frustration—Bumble, probably—I wondered what would happen if I signed up for Seeking Arrangement, a so-called “sugar daddy” dating website that earlier this year rebranded itself as Seeking and announced itself “the largest dating website for successful and attractive people.” (The unsuccessful and unattractive need not apply, one imagines.)

Seeking Arrangement had long been the dating site of choice for young women and older men hoping to find a connection that involved the exchange of money; what that money was exchanged for was up to its users. Now Seeking, which claims it has over 36 million users worldwide, was trying to sell itself as one more dating site. Was Seeking comprised of mostly forty-something sugar daddies searching for twenty-something sugar babies? Or could I, a middle-aged women, find something more romantic than transactional on the site? There was only one way to find out: gonzo journalism. “Start Dating Up,” which Seeking has trademarked, the website beckoned. I paid $19.99 for a 30-day subscription and created a profile.

In a way, Seeking isn’t that different from other dating websites. In fact, I recognized some of the men’s profiles from regular dating websites and apps I’d been on. Many of the men were younger than I’d expected. I’d thought the male users would be middle-aged, moneyed types on the prowl for young woman that appreciated the simplicity of a tit-for-tat exchange. Instead, I found a mix of tech nerds who’d struck it rich and whose screen names occasionally underscored their love of the blockchain and bitcoin, average Joe types hunting for something quick who figured it was easier to find it on Seeking than at a bar, and successful executives who seemed to be interested in a relationship they believed they could control through money.

But were these guys as wealthy as they claimed? On their profiles, they could share their net worth and quite a few claimed to have a net worth of $100 million or more, which seemed unlikely, given that a 2015 report from the Boston Consulting Group found that there were over 5,000 households in the U.S. worth $100 million or more. Some of the men wanted a sugar baby and said so. Some wanted something that might start out transactional but would turn into something more, even marriage, down the line. One, who was married, was looking for a woman who would move in with him and his wife. Another, a handsome young man who related he’d done well when he’d sold his last company, no longer had to work and wanted to find a girl who would travel the world with him on his dime.

I got a few messages, but only a handful. While the site had been rebranded, it was clear that most of the guys were looking for women who were far younger than me. Then I came across the profile of an older man who was looking for tall women with big feet. I’m 6’1” and wear a size 11 shoe. He was looking for The One, he wrote. Was I it? I tried to picture how it might work, me with my tall body and my big feet, and him, far away, with his interests and his self-proclaimed successes.

It was easy to get sucked into thinking about romance as transactional on Seeking, a place where it was normal to calculate one’s worth and then try to sell it. But something stopped me. Seeking was one more dating website, but one where sex and love were commodities. I began to feel grim and a bit cynical, which wasn’t how I wanted to feel. So I deleted my profile.

Photo credit: Clayton Cubitt