The idea of wealthy older people supporting struggling younger ones is nothing revolutionary, after all—look what Peggy Guggenheim did for Jackson Pollock or the Tuohys did for N.F.L. star Michael Oher. So what if I had to tap into my inner geisha to secure a patron?
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. The idea that mixing money and mating is inherently bad, I reasoned, was a fallacy based on our collective obsession with moralizing sex. Mating rituals involving the exchange of gifts—be they hunks of meat, small fishes, or diamond rings—are ingrained in many species, from apes to seabirds, to humans. It is only natural for males to target cues to fertility such as youth and beauty, and for females to be drawn to displays of resources. Why sneer at suspected gold diggers like Heather Mills or the late Anna Nicole Smith if they were merely following their evolutionary instincts?
With all of this in mind, I created my Seeking Arrangement profile. Since I was still a bit hesitant about how far I’d be willing to take my experiment, I signed up using the pseudonym Annabelle Walker. The site, which launched in 2006, has about 420,000 members, of which roughly one-third are sugar daddies and two-thirds are sugar babies (sugar mommies account for less than one percent). While sugar daddies pay $49.95 per month for a premium membership (or $1,200 a month for Diamond Club certification, which requires verification of one’s net worth through tax-return data), as a sugar baby I was able to join for free. I uploaded two photos and listed some general information about myself, and I stated “open, amount negotiable” in the space that asks what you’re looking for. (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.
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?”
“Yes, I had one girlfriend,” he said, his attention consumed by pieces of beef sizzling atop a hot rock. “For a year. It ended in June.”
“Why’s that?”
“She wanted to get married. I’ve seen guys go through with it. Even with a pre-nup, though, you’re at risk.”
“Right,” I said. I allowed Hank to feed me a piece of meat and chewed thoroughly. I was beginning to understand his relationship philosophy: renting a girlfriend is a safer alternative to investing in a wife. I decided to steer the conversation toward the mutually beneficial terms of our would-be coupledom.
“How do you see this working?,” I asked.
He responded without hesitation: “If I want to go with my girlfriend to St. Barth’s for two weeks, she’s not going to be left behind because she needs to write copy all day to make 500 bucks to pay her cable bill. A girl, if she’s going out a lot with me, cannot be wearing the same thing all the time, so of course I’ll buy her her Louboutins and Gucci handbags.”
“That makes sense.”
“I don’t want to feel like I’m paying for company, though. The less she asks for, the more she gets.” If his expression could speak, it would have said, “Don’t expect cash, bitch.”
“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?
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.”
“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.
I examined my gift—an iPod—and said, “Thank you,”
determining to be extra pleasant during brunch.
We both ordered eggs, and by the time our food arrived I had grown to like Charlie. For starters, he provided an earnest explanation for joining Seeking Arrangement.
“I can’t separate the fact that I have resources from who I am,” he said. “It’s part of me. And it’s something I have to offer twentysomethings.”
“I completely agree.”
“I married young, you know. And I remained married for nearly 30 years while I was raising my kids.”
“How old are they?”
He chuckled before admitting, “It’s kind of weird. They’re your age.”
“It’s not weird at all,” I said.
Charlie turned to Seeking Arrangement, he explained, because most of the women he had been meeting wanted to settle down. “I don’t want another family,” he said.
“I promise you I’m not in the market for one,” I told him, and then asked, “Have you ever done this before?”
“I’ve never been in one of these relationships, exactly. But I’ve certainly been generous with previous girlfriends. And since joining the site, I’ve been on a few coffee dates. Pretty positive experiences, actually. I met an editor for a fashion periodical, a translator for the U.N., and a girl whose dad”—he stopped to laugh—“whose biological dad had just cut her off. The only negative experience I had was with a girl who was dating a hedge-funder. She said he had given her her nose and her Birkin bag, but that she needed cash. A bit mercenary for my taste.”
Over the course of two hours, Charlie and I discussed everything from the challenge of monetizing an Internet business to how laughable it is that one of the biggest distributors of pornography in the U.S. is the devoutly Mormon Marriott family (thanks to the in-room entertainment they offer at their ubiquitous hotels). We truly clicked.
That Friday, following a week of kind reminders from Charlie that he had enjoyed my company and found me to be pretty, we met for cocktails at a cozy bar in Tribeca. Again we had a lovely time, although I had to cut it short to attend a dinner at eight p.m.
When I stood to leave, Charlie stopped me. He turned suddenly serious. “Would you have sex with me?” he blurted out.
Almost without thinking, I said, “Of course!”
“Why?” he asked. A trickier question.
“Why not?,” I replied cheerily.
“Bad answer.”
Fuck, I thought—I didn’t want to lose Charlie. In an effort to ease the tension, I changed my tone and said, “Let’s see how it all unfolds.”
“O.K.,” he said. “For now I’ll put you in a taxi.” He kissed me and overpaid a cab driver in advance for my fare.
I felt awful the rest of the evening. Charlie was everything I could want in a sugar daddy—I liked and trusted him, and he would have supported me happily. And yet, when faced with the reality of sleeping with him, I couldn’t mask my apathy.
The following day, Charlie texted me: “Hey! Doing errands in SoHo. Wanna shop (on me of course!) at Prada??? Balenciaga? Just a lark!”
His willingness to spoil me before we had done anything more than peck was startling. And while the shopaholic in me wanted swag, I was unprepared to meet the sex-pectations couched in his request.
I told Charlie that I was getting my hair done that day, and the next time he asked me out I said I was sick. I felt lousy about letting our relationship fizzle, but it would have been worse to prolong it. It was difficult to concede that I might be as much of a sucker for conventional wooing as the next girl, and frustrating to realize that I’d have to find another way to make a living. But it’s one thing to intellectualize something and quite another to live it.
When I started dating through Seeking Arrangement, I thought I was someone who could enter into a relationship for financial reasons and not feel cheapened by it. Ultimately, I realized that I’m not that progressive, or that, for whatever reason, being financially independent means something to me. Even without the safety net of a sugar daddy, I took a risk and quit my day job—a decision that rendered me unemployed, uninsured, and uncertain about where the money for next month’s rent would come from.
As it happens, soon after giving up on my idea of becoming a sugar baby, a man on the Forbes 400 list of the richest Americans asked me out. He sent a chauffeured Bentley to pick me up, and we enjoyed a spectacular meal at Masa, in the Time Warner Center, where a master chef prepares each course from scratch based upon your personal taste. I resisted the temptation to ask for rent money in place of a fancy meal next time (although I didn’t see the bill, it was probably roughly equal to my monthly rent). Such a request might fly with a sugar daddy, but this über-rich gentleman was pursuing me by traditional methods. What separated him from the men I dated through Seeking Arrangement was the fact that he didn’t seem entirely comfortable with being wealthy. “You can’t take any of this with you,” he said with a shake of his head after showing me his penthouse apartment. He also told me that he resented being contacted at least once a day by some friend of a friend of a friend looking to exploit him. In truth, by letting our romance drag on for longer than I would have had he not been a billionaire, I may be as guilty as those far-removed acquaintances. When it came time to move beyond snuggling, I finally succumbed to my inability to fabricate feelings for him. Apparently it’s not just conventional courtship I covet, but love.
By seeking out a man who could provide for my material needs, I thought I was simply following my evolutionary instincts. In fact, there’s another biological impulse that I didn’t consider, and wasn’t even aware of until I spoke to Dr. Helen E. Fisher, a research professor in the anthropology department at Rutgers University. Her pioneering work has shown that love is not an emotion but a drive, and that what we experience as love triggers the brain’s reward system in much the same way cocaine does. In the search for a desirable partner, it seems, we can’t rely on any one factor alone. Despite what eHarmony might claim, there’s no special formula that can help us find the person who will give us that perfect buzz.
