20 ways to play your lover: How the rich do infidelity differently

It seems like every other week a juicy new divorce makes its rounds in the media. Most of these stories involve very wealthy people (often celebrities) who have been unfaithful in some way. Reading large-than-life divorce suit after larger-than-life divorce suit, we started to notice some common denominators. It made us think. So we made some calls, bought some drinks and discovered exactly how super-rich New Yorkers cheat and what makes their approach to infidelity unique.

Read the full story here. 

1. They outsource: In all areas of day-to-day life, wealthy New Yorkers rely on a vast service economy, from real estate brokers, attorneys and tech gurus to doormen, drivers and concierges — and their sex lives are no different. Brokers procure their love shacks. Attorneys keep them out of trouble. Accountants cook their books. Concierges book their dates. And app developers make it all very, very convenient.

2. They shop close to home: For those who prefer to pay to play, any night of the week, the King Cole Bar at the St. Regis, Bemelmans Bar at the Carlyle or The Mark Bar at the Mark Hotel are lousy with high-priced hookers. Especially, the Mark — believe us, we met them.

3. Location is key: When it comes to traditional affaires de cœur, wealthy New Yorkers prefer to court further afield. The denizens of Park Avenue prefer to shake it with their sugar babies Downtown, or even in Brooklyn. Likewise, Downtown’s faster, newly made multimillionaires enjoy the fauxsophistication of wearing the linens thin north of 42nd Street.

4. An office can be a perfect hiding place: “[Closeted] gay men tend to go to Brooklyn, or they go to their office [after hours]” for affairs, says divorce attorney Nancy Chemtob, who represented Tory Burch, Annette Lauer, Tiki Barber’s ex-wife Ginny Cha, Star Jones, Stephanie Madoff, and Diandra Douglas.

She explains that offices are more popular spots for closeted or bisexual men to rendezvous because two men checking into a hotel still raises more eyebrows than two men walking into an office on Madison Avenue.

5. They never take work home: One place wealthy adulterers almost never conduct their affairs is their own homes.

“In eight years of doing this I have only seen three times where people utilized their home and brought their lovers back,” Herman Weisberg, a retired NYPD detective turned private eyes, says. “Nobody does that. I almost fell off my chair the three times I actually saw that. It turns my stomach. That’s the house your spouse probably helped pay for and now you are in bed with your girlfriend or boyfriend. That is pretty unheard-of. If you are going to get the heebee-jeebees about something, it’s going to be having sex with your lover in your own home.”

6. Rooftop bars are essential criteria for hotel hookups: “If you are spotted [going into a hotel elevator] you can always tell a spouse, ‘I was at the bar. I wasn’t in a hotel room.’” Weisberg, says. “Unless they have their pants inside out, there is no indication of what they were doing. It’s a easy explanation.”

7. Real estate brokers are better than pimps: “Sex and real estate are married in so many ways,” says a high-end Manhattan broker who has sold or rented a half-dozen “glorified girlfriend dorm rooms.” He adds that certain brokers traffic in “hot tail for single dudes” and then make their dinero arranging the lease on a love shack.

8. Landlords have it made: Major Manhattan landlords are even better positioned for infidelity than the merely rich. When you own hundreds or thousands of units across the city, how easy is it to take just one off the market for your mistress?

9. Class is as important as geography: High-net-worth people very rarely gravitate to other high-net-worth people for affairs, our sources said.

“It’s obvious and probably not necessary for me to mention that money is very intoxicating” for working-class paramours, Weisberg says. And the clear appeal of enjoying a poor student or a struggling actress is the power of money to lure a lover and better facilitate “favorable situations.” Even vanity is no substitute for the sexual thrill of conquering a working class lover.

10. Beware the money trail: The purchase of a property for a mistress involves a fairly complex monetary shuffle and paper trail. If, for instance, a spouse takes a particular interest in the finer points of their marital assets, the jig could be up. It becomes a matter of playing “how to hide $1.5 million” with your accountant-turned-accomplice — a game that may substantially increase next year’s Christmas bonus. You have to figure out how to make a big financial play look mundane.

11. Technology has changed everything:  “As soon as a client comes into my office, I say, ‘Can I see your phone?’” says Chemtob. “A spouse can enable the Find My Friends app on their spouse’s phone without them knowing. So I turn it off right away. People come to my office and say, ‘I called my wife and she says she is with her friends at SoulCycle but Find My Friends showed her at the Four Seasons Hotel on 57th Street — and she wasn’t having lunch!’”

12. They love dating apps just like the rest of us: Wealthy clients were quick to latch onto digital dating services like Ashley Madison, Tinder, Grindr, Match, JDate and even Christian Mingle, leading to a spike in affair-related divorces.

13. Everyone encrypts: “The biggest way people get busted is on their second iPad,” a Manhattan playboy, who spends half his year abroad, told LLNYC from his phone while lounging poolside in Ibiza. “They leave an iPad at home and a text from some girl pops up while their kid is watching a video.” Now, he says, everyone has learned to encrypt their text messages with services like Telegram.

14. Adultery has met the sharing economy: “My friends view sugar daddy sites like Seeking Arrangements as very efficient,” a well-connected Upper East Side mogul said. Users say that like Airbnb or Uber, sugar daddy sites are unlocking unused inventory (i.e. people) and ironing out the inefficiencies of sex.

15. Attitudes are changing: When you spend your springs in Provence, your summers in Capri and your winters in Gstaad — and a Central Park-adjacent aerie somewhere in between — you get used to dealing with cultures where it is not considered as shocking to have a relationship outside of marriage.

17. And recreational sex is increasingly permitted: “You have to make a distinction between someone who is having an affair and someone having recreational sex,” our UES mogul said. “There is a big difference between an emotional affair and somebody going to Vegas and getting a blowjob. If the wife finds out about that, I don’t think they are going to get a divorce. Some couples don’t look at it as a deal breaker as long as the wife isn’t embarrassed.”

18. But three-ways still cause trouble: “I have a lot of threesome issues,” Chemtob says. “There was one where the husband said, ‘I’ll buy you a major piece of jewelry if you let me be single for a week.’ She said okay. He went out with a woman for that week and he ended up marrying her later.” Another time “the husband wanted a threesome. They had the threesome and the wife ended up falling in love with the other woman.”

19. Prenups trap spouses: Prenups are almost a license to misbehave. Spouses have to turn a blind eye to infidelity, or they stand to lose their lifestyle and their friends.

20. It’s an open secret: Once you start asking about adultery, it’s next to impossible to meet an adulterer. It’s always the other man or the other woman. Always a friend, or a friend of a friend. Always, “I knew a guy who did you won’t believe what.” But once you’ve stopped insisting upon adultery and start listening, you start hearing things.

You start to hear about “absolutely scandalous” trips to Marrakech, where everyone’s boyfriend has a boyfriend, and where the boys are so young and so “well-groomed.” You catch young wives discussing their paramours on the Montauk-bound Long Island Rail Road car. At the Rose Club in the Plaza Hotel, the lascivious braggadocio of boardroom-worn men is broadcast at top volume over martinis.