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.

Damn, I barely made any money tonight,” Brian was saying. It was three in the morning on a recent Friday, and he was cooking dinner (rigatoni alla vodka with pancetta) for his roommates. Tonight had been prix fixe night at Pacific East, which is always a semi-apocalyptic professional experience, rivaled only by Hamptons Industry Super Sushi Monday (when the fish is half-price).

“Every other day of the week, people go in there and drop $100 a person without flinching,” Brian continued, placing the saucepan on the burner. “Celebrities, wannabe celebrities, you name it. George Steinbrenner’s [business] partner was in here the other day—you could tell because he had on a Yankees World Series ring. Night before that, I overheard some dude at the bar saying to another dude that he’d write him a check for a million dollars on the spot for the guy’s watch collection.” He sprinkled in some pepper. “Then tonight comes around, and you have people literally asking for a glass of water, sugar, and a lemon so they can make their own lemonade instead of paying for it. And it’s the same people!”

“I love Howard Stern. He’s the best tipper in the Hamptons, hands down.”

Dinner was served. As Ed and Rick watched TV, Brian and Lu, who also works at Pacific East, discussed the often beguiling environment of the restaurant world, where ego has a way of trumping efficiency. Both of them are fond of the trendy vibe of Pacific East—largely because it translates into solid tips—but sometimes it can be perplexing. Like, what’s up (Lu wondered) with the team of security guards—complete with Secret Service–style earpieces—brought in every Saturday night? To maintain the peace in a place that never gets remotely out of hand? And why (Brian wondered) are the bartenders called “mixologists” when all they do is make drinks like anywhere else?

Sure, the purpose of this is to give the employees a sense of class and authority, yet this often backfires. The other night, a waiter was fired for packing a few bottles of water ($8 on the menu) in his car, having forgotten that, push comes to shove, he was just a waiter. Then, a couple of days later, another server was canned for confronting a VIP customer who tipped him $40 on a $500 check that was picked up by the house. “Now that was clearly a dumb move, and he had to go,” Brian said. “But I have sympathy for the guy. How do you not tip someone well on that kind of bill? It’s amazing how cheap rich people can be.”

Helping others unwind has an odd way of winding you up, which, when you don’t get home from work until 2 a.m., can make sleep a difficult feat to pull off. The gang sat up late into the night, as always, channel surfing: VH1, soft-core porn on Cinemax, that channel that tells you what’s on other channels. At one point, they flipped past a clip of Howard Stern.

“I love Howard,” Ed yelped between sips of a Corona. “He’s the best tipper in the Hamptons, hands down. One hundred dollars, no matter the bill.” And with that, Ed yawned, blew Howard a good-night kiss, and ambled off to bed.

Ed thinks of their life in the Hamptons as The Real World meets Survivor.

Rick was not happy. “It’s a vicious scam,” he was saying, as he watched Ed lug four precariously stuffed trash bags out to his car before heading off to Bamboo—to be deposited at “an undisclosed location.” Tensions between the year-round locals and the conspicuous consumers are always palpable out here, and often bubble to the surface in strange ways—like, say, not picking up trash, an East Hampton policy, meaning you have to pay $80 for private service. Those living a life like Rick’s often find themselves caught in the crossfire of what (from his vantage point) seems like very petty social warfare. “Basically, these people charge the money because they can,” said Rick. “I guess I can understand. But still—$80! That’s decent money to us. I refuse to do it. I’m out here to pay for this car”—a Nissan Altima, the first new automobile he’s ever purchased—“and by the end of the summer, I don’t want it to smell like a junkyard.” (Ed, for the record, has got a new car, too, a Mazda, but somebody’s got to deal with the trash.)

This is another way in which these housemates exist in a sort of no man’s land, not quite locals, definitely not tourists—a similar (if dramatically less intense) state of social invisibility shared by the crews of mainly Latin American landscapers and kitchen workers. As a result, the housemates tend to stick to themselves. “I really only hang out with servers,” says Lu. “I tried making friends with this girl my age who’s out here living at her parents’ house, but it was sort of impossible. We’d go out to a bar, and I’d be looking for work, while she’d be obsessed with finding a rich husband. After about three minutes, we didn’t really have anything to say to each other.”

There are exceptions. Brian, for one, found himself briefly dating a woman who often eats at the restaurants where his housemates serve food. Boyishly charming and flirtatious, he was out one night in June after work and found himself chatting blissfully with a stunning older blonde. A few dinners later, they seemed to have much in common: Both were dealing with divorces, both were looking to start new phases in their lives. Then he went to her house. “I swear to you, her pool is literally the size of our entire place,” he says. That was somewhat alienating, the first time Brian had truly understood the expression “trophy boy,” which left a bitter taste in his mouth.

Not that he couldn’t adjust. In fact, her estate became a kind of vacation home not only for Brian but for the whole crew, whom Brian once invited over as if it were his legitimate residence. On a day off, they lounged by the pool, grinning a little mischievously, catching a brief contact high of how the other half lives: lazy days, quality alcohol. “We were over there in the afternoon drinking Perrier-Jouët mimosas like it was cheap champagne!” recalls Rick. “When we had to leave, we were like, Okay, time to go back to the crack den.” In the end, money did come between them—in a manner Brian still has trouble wrapping his mind around. “She was always paranoid that her ex-husband was paying me to go out with her and dig up dirt so she wouldn’t get anything in the divorce,” he explains. “It was unbelievable! We’d be in a restaurant, right? And she wouldn’t allow any vases or candles on the table because she thought there were cameras hidden in them! I tried over and over to explain that I didn’t give a damn about her money—that I was just looking to have fun—but she didn’t believe me. I liked her, but come on. What am I supposed to do with that?” The yacht was glossy white and glistening in the sun like a coin. B. Smith’s faces out onto the Sag Harbor Yacht Club, and during slow moments like this, Michael likes to stare at the boats—or, specifically, the women on the boats. At present, his eyes were fixed on a blonde sporting a sleek black bikini, walking back and forth on the deck, doing whatever it is one does on the decks of boats. Her skin had the taut, burnished sheen of someone who (Michael figured) dropped $200 on a facial the way he dropped $3 for a bar of soap. “Now that’s a beautiful woman,” Michael said with a sigh. Originally from Alabama, he still speaks with a slight southern lilt. “But, you know, I have to say that her greatest accessory is the boat. Think about it. Without that, would you notice her if she walked by you on the street? It’s incredible what money can do to people.” The woman’s husband appeared from below deck—a heavily perspiring gentleman with a potbelly who looked twice her age—and planted a kiss on her forehead. Michael shook his head, and then went to deal with a customer who was wondering why he was being charged $11.03 for his watermelon martini when it said $11 on the menu.

“I think this whole lifestyle has tweaked my head a little,” Michael confessed later that day, expressing something everyone in the house has felt at one time or another. He was standing in the kitchen, eating a Snickers bar for lunch. Though Michael has no personal address, he recently bought a BMW—an example of how working in places like the Hamptons can misalign one’s priorities. “I’ve spent years going from resort area to resort area—after a while, you forget what normal is. You want to drive a certain kind of car, eat a certain kind of food. You get used to seeing entrées that cost $40, and then you go out and spend that, forgetting that you don’t really have the money.”

“You get used to seeing entrées that cost $40, and then you go out and spend that, forgetting that you don’t really have the money.”

Not that he envies those he sees piling into Nick & Toni’s every night—not too much, anyway. Michael prides himself on being laid-back, calm in any situation, and some of the people he waits on often seem to be looking for something to stress about. Take the regulars at Nick & Toni’s. Nice people, without a doubt, but the other day they protested an appetizer’s price being raised from $12 to $14 so vehemently that the restaurant went back to the original price. “I truly don’t know if there is anything you can say to something like that,” Michael said. “Half these people pay with black Amex cards—you can go out and buy, like, ten Ferraris with those.” That said, the perks can be pretty surreal: On a recent night, for instance, Christy Turlington offered Michael a glittering smile. Granted, he had just dropped off her entrée, and she was there with her husband, Ed Burns, but you never know.

Speaking of Nick & Toni’s: One night when she wasn’t working, Lu decided to visit Michael at work. Waiters tend to have a lot of cash in their pockets, and Lu didn’t flinch when ordering a feast. Nearby, a woman with a wine-flushed face was comparing the war in Iraq with the Clinton-Lewinsky scandal (“I’m telling you,” she said repeatedly, “a blow job is not a trillion bombs!”) within earshot of George Stephanopoulos, who was dining at a nearby table and who Lu knew was famous but couldn’t remember exactly why.

Lu stood up to use the ladies’ room, and as she made her way through the restaurant, a curious thing happened. She found herself face-to-face (again) with Calvin Klein, who was having dinner with a friend. How strange. How funny. For a split second, it was like seeing an old friend, and Lu tried to make eye contact, wondering if the designer would recognize her. Nope—he didn’t, not even close, which was just fine. Feeling as if she had a secret, Lu walked past his table, grinned, and whispered “Hello” under her breath.