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A Holly Golightly for the Stripper-Embezzlement Age

After the crash, financier Ken Starr was revealed to be one of the greatest hustlers of our time. But he had nothing on his fourth wife, Diane Passage.

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The Grand Havana Room is good, if you can get past the doorman. The Oak Room at the Plaza is the easiest game in town; just go early in the week, like on a Tuesday night, because later it fills up with tourists and C.P.A.’s from New Jersey. Wednesdays, Jean ­Georges draws an affluent after-work crowd; a girl who knows what she’s doing can easily get a free dinner along with her drinks. In fact, if you’re looking for a man who likes to visibly spread it around, pretty much all of the Vongerichten properties are a good bet, though if you prefer a long-term arrangement with a wealthy, mature gentleman, you’ll want to concentrate on the uptown ones, such as the bar at the aptly named Mark Hotel, on 77th Street and Madison Avenue. And of course there are circuit standbys like the Peninsula rooftop, where, on a recent balmy weeknight, Diane Passage is sitting at a table holding court with, as she had indicated by text message, several “v. handsome men.” She’s relaying a story about another evening at another perennial, the Waldorf-Astoria, where a guy paid her $100 to kick him in the balls: “He was into humiliation or whatever.” She giggles. Passage is a petite, smoky-eyed Kardashian brunette, and when she laughs, her grapefruit-tree physique bounces merrily. “It was so weird.”

“What’d you do?” asks one of the men, a ruddy real-estate developer we’ll call Barry.

“I kicked him in the nuts!” she says, like duh. She’d been sitting at the bar with a friend who “kind of looks like a hooker,” so it wasn’t surprising when the well-dressed man who’d bought their drinks made a business proposal.

“We went into this little area and he was like, ‘First, go into the restroom and make me wait,’ ” she says. “So I went into the bathroom for like fifteen minutes and I was texting all my friends and then I came out and I kicked him in the nuts and he was like”—she drops her voice down to a meek whisper—“ ‘Thank you.’ ”

Passage giggles again, and the ensuing undulations manage to pull Barry’s attention back from the blonde who’d just passed by.

“Shots!” he says decisively. His friend, let’s call him Paul, a tall, paunchy private-equity manager who was quiet much of the evening but has become considerably more animated after a trip to the bathroom, pounds the table in agreement. When the shots of Patrón arrive, Passage sips hers slowly; when Barry protests, she just smiles. The men, meanwhile, are wasted.

“Am I a good boy or a bad boy?” Paul asks.

“Aw, you’re a good boy, Paul.” Passage laughs. She laughs a lot.

Passage is one of those people that it feels like New York invented, though they thrive wherever male egos and dumb money coexist. She’s the kind of woman who is able, through physical charms, nifty tricks of persuasion, and sheer gall, to inspire men to pay for … well, everything. She’s like Holly Golightly, if Holly Golightly had to kick a guy in the nuts when she went to the powder room. Which, in postrecession New York, she might have.

But not so long ago, Passage wouldn’t have entertained the idea of sexually humiliating a man for a mere $100. She wouldn’t have been at this bar, with these guys, taking a small puff of Barry’s spit-covered Habana cigar because he’d thrust it in her face and said “Suck it.” Until quite recently, Passage was the happy protagonist of a modern-day fairy tale: A single mother who, four years ago, was plucked off the dance floor at Scores by a financier who promised to change her life. And change it he did.

At first glance, Kenneth Starr was no one’s idea of Prince Charming. He was in his sixties, he was married. But he was a money manager (not to be confused with the Whitewater investigator) and clearly successful, if the list of phone numbers of clients he scrolled through on his cell phone to impress the strippers was any indication: Al Pacino, Barbara Walters, Bunny Mellon, Candice Bergen, Caroline Kennedy, Diane Sawyer, Harvey Weinstein, Nora Ephron, Scott Rudin, Warren Beatty, Carly Simon—it went on and on, a Who’s Who of famously wealthy people in America in the 21st century. He had plenty of cash to throw around, especially, it turned out, when it came to Passage. After his whirlwind divorce and their equally whirlwind Vegas wedding, Passage moved with her son from a small walk-up to a $7 million condo on the Upper East Side in a building so sure of its fabulousness that it was called “Lux74.” In a year, she went from rubbing customers’ legs at bachelor parties to rubbing shoulders with celebrities at the Vanity Fair Oscar party.


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