Hotels that Help You Cheat

Today's finest hotels and restaurants work hard to accommodate their guests' dalliances. Sara Reistad-Long investigates the secret tricks that keep philanderers one step ahead of their spouses. Plus, the best places to cheat.

10.13.09 11:16 PM ET

There are perks rich people enjoy—chauffeurs, life coaches, puppy au pairs—that they consider essential to their well-being, and for some, “cheating assistant” is high on the list. Because when you’re paying top-dollar for a penthouse hotel room or a corner banquette at a luxury restaurant, the establishment’s staff should know enough not to call your wife by your mistresses’ name.

To ensure this, the owners and managers of the world’s most exclusive restaurants and hotels pull out all the stops to make sure their best customers can conduct their affairs there with ease. “I had a regular customer who, on the same day, brought his mistress in for lunch, and his wife for dinner,” says Jean-Luc Le Du, an award-winning wine professional (now owner of Le Du’s Wines) who spent 10 years running the wine program at Daniel, celebrity chef Daniel Boulud’s four-star Manhattan flagship. “The expectation was that we wouldn’t even blink. That probably protected him better than anything.”

“Our policy was to keep what we referred to as a client ‘résumé’ on file. On it, we’d have any information we deemed relevant to making the stay seamless and comfortable for all.”

You could say it takes a village to cheat. Michael Greenlee, who until 2007 was the wine director at Gotham Bar and Grill, another New York restaurant known for its VIP regulars, says this is what clients are paying for. “There are a handful of really top-tier establishments that come with a service standard where all the t’s are crossed and all the i’s are dotted. Part of the package is to offer a very comfortable, safe place for the customer to do business, whatever that business might be.”

How do they do it? Like they do everything at these establishments: with flawless technique and artistry. The Daily Beast spoke to some of the country’s top restaurateurs and hoteliers about keeping adulterous guests under the radar.

Scour for Up-To-Date Information about Your Clients

To this day, Julian Niccolini, the co-owner of New York’s Four Seasons restaurant, spends his mornings scouring, clipping, and saving newspaper articles containing information that might be relevant to his top clients’ behaviors. Nor does his attention to detail end there: “I've had to juggle a wife and husband, each dining out with their respective boyfriend and girlfriend,” he says. “It can sometimes come down to timing and finessing everyone’s trips to the restroom. Luckily, we have two sets. And two exits to the restaurant, as well. A lot of it involves engaging one party in conversation for just the right about of time. It’s a performance.”

Greenlee says that during his Gotham years he actually had an RSS feed on his computer for news developments that helped him predict how to interact with a newsworthy customer on any given night. Was the woman in the low-cut dress the rumored partner in a just-announced financial merger, for example, or the consolation prize for a deal gone south?

Maintain a File on Their Personal Lives

For larger establishments with lots of employees, the personal touch may need a little practical support. “When I was at the W Hotel New Orleans, we were always getting NBA teams passing through,” says the person who for years headed up group sales at a number of the brand’s outposts. “Our policy was to keep what we referred to as a client ‘résumé’ on file. On it, we’d have any information we deemed relevant to making the stay seamless and comfortable for all.” This included the names of wives and mistresses, along with the guests’ preferences of whose calls to put through. Once, she says, an especially colorful list fell into the hands of a wife. The results, she says, were entirely “as expected.”

This file-keeping practice is more common than you might think. During a recent stay at the Westin Grand Cayman, one top New York ad exec was surprised to hear the concierge refer to his “file,” something he later learned had been passed along from one branch of the chain to another.

Train Your Staff

Last year, following the Spitzer scandal, the management at One If by Land, Two If by Sea, a mainstay of the New York candlelit-date circuit, decided to hold a pre-Valentine’s Day staff briefing. “We find that on February 13 a lot of men bring in their girlfriends, and on Valentine’s Day they bring their wives,” says general manager Rebecca Martino. “It’s been so common, and in light of what happened, it just made sense to get everyone on the same page.”

Martino adds that whenever a regular client shows up with an unfamiliar woman, the staff policy is to start the evening by acting like they’ve never seen him before (a tactic also rumored to be part of the Ritz’s training instructions). If the woman gets up to go to the ladies room, a manager or senior waiter will take the opportunity to greet the customer, and—ideally—get some instructions on how familiar to act.

Even so, some places aren’t taking any chances. The self-described “Moroccan fantasy restaurant” Le Souk Harem in Manhattan recently decided to require all staff members to sign a letter of confidentiality assuring that they won’t divulge anything they see or hear. “We had to; they see and hear a lot,” says the restaurant’s publicist, Steven Hall.

Let Your Clients Feel Like They’re Hiding in Plain Sight

"In the center there you can see Ralph Lauren,” Julian pointed out in the Four Season’s Grill Room. “And that's Kissinger over there,” he continued, gesturing with his chin. “And in the far corner by the wall, that man is having lunch with his mistress."

“Part of the appeal of taking somebody out is to feel like the two of you are really having this high-level restaurant experience,” says Greenlee, now the general manager of Tuck Beckstoffer Wines in Napa Valley. “So the challenge for us is to make clients engaging in extra-curriculars feel like they’re the center of the universe, while, actually, being somewhat out-of-view from other customers.”

Specifically, Greenlee says, “The whole strata of Gotham was designed around keeping the premium spots—meaning those with the most space, the best waiters, and so forth—a little less exposed.” One trick used at the restaurant was to position a few very inviting tables against a far wall facing outward. That way, both customer and date can get the full effect of the action and, indeed, feel like they’re presiding over it. The “action,” meanwhile, is none the wiser.

It’s a popular approach. Joey Allaham, managing partner at the Oak Room in New York’s landmark Plaza Hotel, says they’ve also used design in this way, employing dim lighting and “a few cozy tables very much tucked to the sides.”

At All Times, Ignore and Deny

“Interestingly, when I was first learning the bar trade at the LAB Bar in London, one of the first tenets we were taught was to never, under any circumstances whatsoever, greet a patron with even a hint of familiarity unless you were first acknowledged in said fashion,” says Jamie Gordon, now a brand manager for Plymouth Gin. “The extended explanation I received—and to this day pass on—is that bars are seen as a refuge from whatever ails elsewhere, so protection of the interests and privacy of paying clientele was paramount to a successful establishment.”

It’s not just your friendly bartender who’s keeping mum. Codes of silence extend to restaurants and hotels, such as Wynn Las Vegas, where one advertising brand coordinator confirmed that employees are told to give out no information whatsoever about guests—from how many people may be in a room, to whether an individual is even there at all. And it goes without saying that at places like these, a forgotten item will never, ever just show up on your doorstep—you’ll have to call yourself to retrieve it.

The sealed-lips strategy becomes useful more often than you might think. At One If by Land, “we frequently get calls from wives, asking if their husbands are here," says Martino. "It can be awful; some will really open up, or pose specific questions about the women they think might be with them. Others will beg. We have to just keep explaining that we’re not in a position to say anything either way. It’s hard to do, but believe me, this isn’t news you want to get from a concierge.”

Turning the Tables: What Makes a Place Good for Cheating?

Pulling together all these pointers, it seems the key to keeping a love affair off the grid doesn't necessarily lie in the most anonymous, unrecognized choice. Like your high thread count linens, discretion is a premium amenity, and the higher you travel up the price-point ladder, the better off you are. For example, practical as choosing a low-cost hotel within a large chain may seem, it appears unlikely the person behind the desk at, say, the Days Inn would spend much time thinking about how much or little to reveal about your whereabouts on a given afternoon. Likewise, it's tough to imagine a scenario where all the staffers at just about any large conference hotel would remember to do something like consistently list and refer to you by a name other than what's on your credit card.

By contrast, not too long ago, a gentleman checked into an exclusive Bora Bora resort with his mistress. He found himself having such a delightful time that he decided to not only extend his own stay past the girlfriend's, but to also get his wife in on the fun. On her arrival, he'd have to pretend, of course, he'd never seen the property before. All in a day's work, the manager said, and proceeded to send out memos outlining a watertight plan for reintroducing him to the resort. Not exactly a service feature you'd find in the brochure. But, for a certain type of client, it's all part of the package.

Sara Reistad-Long is a New York-based writer. Her work has appeared in The Wall Street Journal, The New York Times, Esquire, and O, The Oprah Magazine, among others. She can also be found blogging at, where she explores the intersection of health and delicious food.