It was jarring seeing him like this, so close, so intimate, practically in private. Not necessarily impressive—just flat-out weird. Here was a man you’d seen in a million magazines, on TV a thousand times, his name printed on billboards across America. Here, in short, was someone you’d seen so much without actually seeing him that it was a pretty safe bet to assume he didn’t actually exist in the flesh. Yet here he was. Right there. Touching you. Calvin Klein. Mr. Underwear himself. Who would’ve thought?
“Almost perfect,” the designer was saying, his voice a mellifluous purr, his whole manner preternaturally emotionless. “Maybe try this blush . . . ”
Lu Villarreal couldn’t help but grin. A 25-year-old woman with striking brown eyes and long, flowing black hair, Lu (short for Guadalupe) was sitting in Calvin Klein’s East Hampton mansion, having her makeup “supervised” by Klein himself. She was one of many out in the Hamptons this summer to do the very thing many come to escape—to work, to work whenever humanly possible—and the other day, a funny thing had happened. An almost comically handsome man had strolled into Belles East in Southampton, one of a few places where Lu has bartended, introduced himself as an “event planner,” and asked if she would like to serve drinks at a little housewarming party. Sure, she’d said, imagining a handful of geriatrics sipping dirty martinis and complaining about their internal organs. Twenty-four hours later, she was the designated prototype for tonight’s fleet of servers, her “look” being perfected by one of America’s foremost perfecters of female looks.
“It was so ridiculous,” she said later that evening, sprawled out on the busted futon in the dorm-size home where she was living temporarily with four near-strangers, all of whom were raptly listening to her story. “Before the party started, another server and I snuck off and explored the house. We tiptoed around all these crazy rooms and staircases. I’m telling you, Calvin Klein will go years without seeing some of those rooms.”
Everywhere she wandered, she came across an odd sight: queen-size beds, in corners, in the middle of expansive hallways, on the terrace—all meticulously made. As the guests arrived, Lu wondered, Was this some sort of slumber party? A fashionista orgy? Was the Interior Dude from Queer Eye for the Straight Guy going to get with that fellow named David Geffen, who everyone kept saying was someone? It took Lu a while to understand that, no, those beds—paid for with the same funds that were paying for her single mattress in a bedroom a zillion psychic miles away—would never be used. Like a lot of what you see in the Hamptons, they existed for a simple reason: because they could.
“I see these people at the restaurant and wonder how they got so tan. Then I remember: ‘Oh yeah, there’s a beach here.’ ”
“Can you believe it?” she said to her housemates, smiling in disbelief, sounding as if she’d gone out and spotted a UFO. “I mean, who are these people?”
Imagine, for a moment, a relief map of the United States—only instead of gradations in terrain, you see peaks and valleys symbolizing wealth: random clusters, shifting formations. Now zoom in on the Hamptons during the shimmering summer months: many, many peaks; very few valleys. What you’re looking at is this verdant swath of Long Island from the perspective of Lu, her housemates, and those like them: a destination where waiters have been known to pull in $20,000 in eight weeks by asking the Billy Joels and Jerry Seinfelds of this world if they’d like, say, another $10 bottle of sparking water to wash down that $42 lamb shank. Every season, people migrate here, forming an accidental and generally ignored social class—those looking to get a little richer off the very rich.
There are influxes of such seasonal workers from literally all over the world. And like those they serve, they inhabit a complicated universe often guided by inflated egos, where status is marked in nuances and envy crops up in amusing ways. Take the year-round locals, who find themselves competing with ambitious out-of-towners. Or the small colony of Irish, who ride their bikes over fifteen miles every day to work mainly as busboys and caddies, and who can be found late at night in dive bars dissing the prissy waiters and bartenders they work for. Those waiters, meanwhile, can be divided into three segments. Someone like Lu, up from Florida for the summer, part of what’s referred to as the Miami-Hamptons Cycle, will tell you that it can be annoying chatting with the aspiring actor-model types who come out from the city with the main goal of fostering connections—but not quite as annoying as the college kids who live in their parents’ vacation homes and are clearly just working to feel noble and diligent and obviously don’t understand what it’s all about.
“Money, money, money—it’s all about the money,” says Ed Stein, 39, a generous, sardonic, mildly flamboyant Bayside native who’s been trekking out to the Hamptons to fatten his bank account for four years. He works about 60 hours a week, divided between days at B. Smith’s in Sag Harbor (where he once met Michelle Pfeiffer at Steven Spielberg’s niece’s wedding-rehearsal dinner!) and nights at Bamboo in East Hampton (where he once met a Law & Order actress he’d never heard of!). “Sometimes, I’ll look around and I’ll see all these people in the restaurant and I’ll wonder how they got so tan. Then I remember: Oh, yeah, there’s a beach here. Some people are actually here to relax.”
It is Ed who runs the “admittedly ghetto” share home on Three Mile Harbor Road where Lu and three others are staying: There’s Rick Simmons, 40, a lanky guy who also works at Bamboo (where the kitchen staff affectionately refer to him by the acronym BGR, for Big Gay Rick); Brian Duel, 43, a Brooklyn-born father of three who recently kicked a 21-year addiction to cocaine and is out here working at B. Smith’s and Pacific East to pay child support; and Michael Wilkins, 34, the enigma of the house, who, when not at B. Smith’s or Nick & Toni’s, is often holed up in the room he shares with Brian, skimming anarchist brochures on “how to become a poetic terrorist,” trying to figure out if it’s a completely ridiculous thing to do or slyly relevant.
They are a motley crew, a microcosm of a microcosm: all up from Florida, where Ed’s house has become a small legend in the restaurant community. Strangers before this summer, they now share the bond that comes from (a) serving some of the world’s wealthiest individuals and (b) sharing very small bedrooms, an even smaller bathroom, and having to deal with a noisy next-door neighbor who keeps one rooster and three semi-feral dogs chained to a tree in his backyard. Ed watches a lot of TV, and he likes think of their life in the Hamptons as The Real World meets Survivor—but on a cable-access budget.