The Secret Lives of Sugar Babies

IT’S A SUNNY afternoon when he sees me, standing in the center of 30th Street Station. He gives me the once-over, barely says a word. He’s not quite what I’d hoped: Two muddied-white knee-high socks appear to mask a fluid build-up in his legs; he has a bald spot that’s surrounded by a bush of frizzy gray hair; his eyes strike me as uncannily cold and beady.

Stuart*, 61, from North Jersey, heaves his luggage over his shoulder and heads off to buy two tickets to Atlantic City, our first-date destination for the next two nights.

We met online two weeks earlier through a website called SeekingArrangement.com, a “dating” website where young guys (like me) and older, ahem, “established” men (like him) can find, as the site’s founder Brandon Wade would later term it for me, a “mutually beneficial arrangement.” I initially connected with Stuart looking for a story—I wanted to understand what it both looks and feels like to be in a strictly transactional relationship. Our initial (and uncomfortable) 45-minute Skype date (where he refused to show anything more than his zoomed-in eyeballs) led to a deal to feel out our in-person chemistry through a trip to Showboat. All expenses paid by him, of course.

On the train ride down I learn that he’s an automobile-parts seller, has never had a boyfriend, and that just a few months ago he ended a two-year relationship with a “straight” Texas guy who was supporting a family. They’d meet halfway for baseball games and weekend getaways in Washington, D.C., where Stuart would, shall we say, be fully serviced. In return, Stuart paid Texas’s bills.

I’m listening. Intently.

He paid for everything?

I’ve got student loans coming due …

And rent is getting awfully difficult to keep up with …

And gosh, I could use some new clothes …

Could I really do this?

IT’S NO MYSTERY why cash-strapped young guys are looking for men like Stuart. As of August, 16 percent of 18-to-29-year-olds in the U.S. were unemployed, not counting the “underemployed,” that legion serving up venti, no-foam, five-espresso-shot cappuccinos at Starbucks. Is it any wonder that they’ve gotten creative with ways to jump to the other side of the counter?

Now consider this: An in-house list released by SeekingArrangement in 2012 ranked Temple University as No. 5 in the list of universities with the largest number of sugar baby sign-ups in 2011 in the entire country. Of the university’s 584 “College Baby Certified” members, 44 are gay men and 123 are bisexual babies seeking a daddy or mommy; in total, the site boasts 4,410 registered gay sugar babies in the region, and 171 gay sugar daddies. Do the math: That’s 26 hungry sugar babies for every one generous sugar daddy.

David is one of these “babies,” a young, handsome, fit guy in a scoop-neck t-shirt complemented by a fitted jean vest, with shiny black hair and teeth so white they glimmer. True to gay form, his personality matches his outfit: He’s flighty, materialistic, and gives about as much thought to the long-term as he does to what socks to wear.

He moved to Philadelphia two months ago, bearing only his clothing, a hair-styling license, and $400 in cash from his last sugar daddy, a guy from Allentown. David’s new one, a 37-year-old man living in Center City, had encouraged his move by gifting him $500 to pay rent, with the promise of more. Just weeks after the big relo, however, New Daddy went AWOL. “One day I text him and say, ‘Are you OK? Are you dead?’ And apparently he’d gotten into a relationship with someone—like, an actual relationship—and didn’t want to tell me,” David says. “I couldn’t be mad at him, but I’d moved here because he said he’d help me out. Then I’m literally just like: Fuck, what do I do?”

David’s had three sugar daddies over the last five years. Atypically, his arrangements were completely non-sexual, with the exception of a one-time sexcapade he endured for rent money. Mainly, David provides a few dirty selfies and his company at dinners in exchange for shopping sprees and cold, hard cash. I had to admit, it didn’t sound half bad.

That is, until the daddy well runs dry. Now devoid of benefactors, David is broke. “I spent the money on nonsense,” he admits. “I’d buy $300 jeans and be like, ‘Whatever.’ Now I go to the sale section.” He says he also lavishly treated friends to ease his guilt. “It does make you feel like shit,” he says of the “arrangements.” “It makes you think, What am I doing with my life?”

Over coffee, he tells me he’s uneasy about meeting a new “daddy” in Conshohocken who appears all too eager to take things straight to the sheets. But any misgivings have given way to financial reality. “It’s a job,” he says.

By contrast, Michael is practically the “poster baby” for sugar relationships. When we first meet, I’m struck by how shockingly put-together he is.

A 30-year-old suburbanite, former financier, and former model, Michael strung together 10 (10!) sugar daddies—one after the other after the other—during a three-year period. First to pay bills, then simply to live a more extravagant lifestyle. The heart-fluttering, Prince Charming type, he’s six feet tall with dark brown eyes, buzzed hair, a broad-shouldered build, and a deep, masculine voice. He’s gay Brad Pitt.

Because Michael wasn’t exactly living on Ramen, he was choosy with the daddies he slept with. Most have been of the harder-to-come-by silver-fox variety, and he insists he only sought romantic men. As an aspiring entrepreneur, he says these men were as much mentors as they were lovers. His go-to daddies were a couple in their 50s who had amassed wealth through the dot-com boom, were physically fit, and, he emphasizes, had all of their hair.

I find his “mentorship” schtick a bit tough to swallow. But I can see how the perks—namely, all-expenses-paid travel—have made his relationships worthwhile. Michael has circled the globe on his daddies’ plentiful dimes: St. Bart’s, Greece, Indonesia, Fiji, southern France. “A lot of it, for me, was being able to see the world in a way that most people don’t get to in their lives—staying in really nice hotels, private jets, yachts,” Michael says. “I don’t think you can imagine it until you actually experience it.

“Unfortunately,” he adds with a sigh, “you can’t stay on top forever.”

REWIND, FOR A moment, to June 9, 2010.

Ben, a then-44-year-old corporate banking executive from the Poconos, had become accustomed to a routine between him and his sugar-baby boyfriend, John: After a four-day stretch of spending time together, John would wake up and leave first on Monday mornings. Ben would wake up later, shower, and leave for work. They had maintained the routine for three years.

This particular morning, however, Ben left for work earlier, out of his normal routine, while his sugar baby, with his long auburn hair and Men’s Health–model body, was still asleep. Ben returned home that night to a goodbye note on the counter.

Rewind again, to June 10, 2007.

After a year of “normal” dating (they’d met on Match.com), Ben realized he wasn’t going to keep what he thought was his soul mate without forking over some cash. John had, as Ben now puts it, “fallen in love with my checkbook.” So Ben wrote a check for John’s new Ford Mustang and treated for lavish meals and trips. In the end Ben offered John a deal: a three-year contract that would staple them together. “It was,” he admits, “like buying a relationship.”

Ben is, in presence and personality, as generous as he is warped by his own fantasy world. He recounts this story to me as if the absurdity is not that he expected to swipe a credit card and buy a Cinderella ending, but that his sugar baby was disobedient, like a wild animal he couldn’t domesticate. “I tried to renegotiate a new contract with him, and he wouldn’t hear it,” says Ben. “I knew without me he couldn’t survive, because he only worked two days a week as a fitness instructor. He didn’t do anything else.”

What John had done was find another sugar daddy: a married (to a woman) anesthesiologist 15 years older and several zeroes richer than Ben who was looking for a boyfriend on the side. “Why would you want a Mustang,” Ben says ruefully, “when you can have a Mercedes?”

I’M CARVING AWAY at my $41 filet mignon when I feel his eyes on me.

Stuart has stopped eating his lobster tail to watch me eat. I take a sip of my cocktail, rest my forearms on the table, and raise my eyebrows, as if to say, “Is there something you’d like to ask?”

He looks at me and, for the first time during our trip, cracks a smile.

“I bet you’ve never had a sugar daddy treat you to something like this, huh?” he says.

I tell him I have not. That, in fact, I’d normally be eating a peanut butter and jelly sandwich.

We leave the steakhouse and move upstairs to our room. He’s promised he won’t “try anything,” but I begin to feel uneasy noticing there is but one king-sized bed. After we watch TV for two hours, he strips down to his undies and motions for me to join him.

True to his word, he doesn’t try anything. But it begins to occur to me that I’m in bed, in a strange city, with a man three times my age I met 12 hours earlier who clearly wants to have sex with me, even if he’s too polite to ask. I don’t get a wink of sleep. By the time the sun rises, my sugar high has crashed.

At breakfast, picking at my food, I feel trapped.

Because the “sugar” lifestyle comes with as many costs as it does rewards. For every Michael gamboling through Greece, there are countless Davids, who accrue a tab of sex and “companionship” for each new outfit or rent check, only to be left scrambling when their daddies disappear. Stuart, I come to realize, isn’t unlike Ben: He believes he can purchase a relationship. It’s not just a commoditization of sex, but emotions. “If I wanted a prostitute,” Stuart told me over drinks the night before, “I’d just hire a prostitute.” But despite the prettied-up “sugar baby” label, he had hired a prostitute. I am, even if in a more emotional sense than a sexual one, his whore.

“You’re not into this anymore, are you?” he blurts out.

I reach for the words I should say: “That’s not the case at all!” Instead, my mouth is agape—like a goldfish out of water, about to be flushed down the toilet.

He rushes to toss his plate and heads upstairs. In minutes I’m practically shoved in a taxi, and we’re on our way back to Philly. Arriving at 30th Street, he limply shakes my hand goodbye. I never hear from him again.

Back in my apartment, I toss my bag onto my bed and trudge to the kitchen and pull out the peanut butter and jelly. It never tasted so good.