How to Have (and Hide) a Hollywood Affair

Illustration by: Zohar Lazar

Gone are the days of thrilling trysts at The Peninsula ("You always have some bellboy willing to drop a dime") as paparazzi and social media drive industry adulterers under deep cover. Airbnb, mon amour?

This story first appeared in the Feb. 20 issue of The Hollywood Reporter magazine.

When it comes to keep adultery under wraps, Steve Kroft seems to have neglected the most important element: location, location, location. The married 60 Minutes newsman's purported affair with a married Harvard-educated lawyer landed him on the cover of the National Enquirer, which also published many of the lovers' text messages — some provocative, some cautionary, with Kroft reminding his partner that flashy attire might be conspicuous at one Washington hotel where they were to meet. Unfortunately for Kroft and his mistress, sartorial discretion hardly suffices when your name is of the boldface variety.

The appetite for information about extramarital tete-a-tetes is as aggressive as ever — and the more salacious the details, the better. Which means the cloak of secrecy around an affair, especially for those in the paparazzi (or tourist cellphone) line of fire — as well as all who work in the surprisingly small town of Hollywood — must be darker and tighter than ever before.

The right location can allow a romp to remain a secret. But despite the sprawling L.A. metropolis around it, Hollywood offers slim pickings for shadowy restaurants or off-the-beaten-path hotels where you won't see someone who knows someone who knows someone — unless you don't mind getting gritty at a rent-by-the-hour drug den or a dive bar in Koreatown. Forget the secluded park in the Valley, the Westside watering hole or the Echo Park eatery because that junior-level development executive who sort of looks familiar could pop up at one of them.

So, what's a cheater to do?

According to sources surveyed by THR, it's no longer trendy to have affairs in such posh Hollywood hotels as The Peninsula, Four Seasons or Beverly Wilshire because the risk of being discovered is too high. These days, it's all about the private condo, the best friend's apartment, an Airbnb rental or places you only can get to by plane — film festivals or the best location of all: on location.

Longtime gossip columnist Janet Charlton, whose website specializes in "character-revealing" celebrity dish, confirms that hotels are out for the most part, unless it's a high-rise hosting a big event "with a lot of ins and outs that wouldn't arouse any suspicions," she notes. "Social media and the paparazzi have changed tryst-having in Hollywood because everyone is a photographer, and they're all over, outside of all the hotels," adds Charlton, who covered an infamous hotel scandal in the '90s when Michael Douglas reportedly was caught cheating at the Beverly Wilshire by his then-wife Diandra with one of her friends. "It's difficult to get away with anything anymore. You're going to get caught."

Adulterers are going to great lengths to cover their tracks and avoid getting caught in the way such stars as Tiger Woods or Kristen Stewart have in recent years. "TMZ has absolutely changed the game," explains private investigator Dan Hanks, better known as Detective Danno. "People have hideaway condos now because there's more privacy there. With hotels, you always have a bellboy or a desk clerk who is willing to drop a dime to get on a regular payroll [by selling a story]." Condos are whispered to be a favorable option for Tinseltown cheaters, with several sources fingering the Wilshire Corridor's stable of luxe high-rises as a popular destination for affairs. Another source cited a well-known producer who once kept a property in the Bird Streets neighborhood of L.A., where he and several male pals used to bring women who weren't their wives for adult fun (THR's source used a four-letter word to describe the expensive pad).

However, those arrangements are available only to the top tier of Hollywood types who can afford to shell out the cash for additional properties or pay powerful lawyers to cover their tracks, adds one source. More common? Affairs on set. "Being on set during a production is akin to summer camp," relays one notable manager. "You're all housed at the same place, having the same experience away from your regular life, reality and responsibilities. And everyone is horny." A producer sums up the small-town vibe: "There's nothing else to do!"

The film-festival scene also is said to be rife with sex-crazed industryites who allegedly engage in affairs they might avoid if not for the freewheeling lifestyle delivered by Sundance, Cannes or Toronto. "It's late at night, you're high or drinking and suddenly you're sleeping around," says one veteran of the biz. And the alibis provided by the locations might as well be dished out on silver platters: "I was in back-to-back screenings"; "I was stuck in an eight-hour negotiation"; "My cell service is spotty"; or "I was at dinner with Ethan Hawke and couldn't pick up."

Cheaters who prefer to keep their dalliances local rely on the discretion of powerful gatekeepers, like maitre d's and restaurant heads. "I often find that someone won't have two [different] women on the same night in the same room but instead on consecutive nights — on a Friday and on a Saturday — so what I won't say is, 'Didn't I see you last night?' " explains The Palm's co-chairman and co-owner Bruce Bozzi. "You have to know sometimes when not to acknowledge that you've seen somebody."

But ultimately, the greatest discretion is required of the cheater (and his or her partner), and adultery is the type of risk-taking behavior that often comes hand in hand with a (false) sense of invincibility, especially in a city of movers, shakers and dealmakers. "In Hollywood, people feel they have license to do whatever they want to do," says the manager. "Everyone feels they're untouchable." That is, until they get caught.

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