The ‘2 Percent’ Aim to Make the Move to Elite Status

Standing by for the upgrade.
The wealthy have become ever-mindful of opportunities to trade up. Illustration by Paul Kisselev

On a sizzling August night, Ironman and I were catching up over spicy hot Thai food while reveling in the icy air conditioning. We shared Instagram diaries of our summer vacations, a digital show and tell, as we nursed spicy green apple martinis with needle-thin, floating peppers.

“Wyoming was truly amazing,” he said as I scanned the photos of his wife, Ubermom, and their trio of impressive and beautiful Ivy League daughters, all clad in outdoor gear and in various stages of airborne activity. Not something yours truly would indulge in but an activity I am clearly impressed by. Ironman looks vastly younger than his years, due to good Latin genes and his workout schedule and easily could pass for one of the 20-something guides in the scroll.

I quickly showed him my workout photo: me hoisting a pitcher of sangria with sliced white peaches and cherries—in the background, the soaring cliffs of Capri. “This is how I hang at the rocks, but we can still be friends,” I offered.

He showed me another photo with an incredible panoramic view.

“And this is the spot where we decided to renew our vows,” he said, showing me a photo of blonde Ubermom holding the rope as he dangled off a razor-sharp cliff.

“If she would have let it go, that would have been the end of me,” he stated.

“Lucky man,” I laughed.

“I‘m glad she held tight.” Their enduring marriage has been remarkable, and they lovingly accept each other.

When I told another couple the rope story at a recent dinner, the wife remarked, “Well, great for them, but if it were Larry [not real name] and me, I would have dropped that rope in record time and not given it a second thought! ” She laughed ruefully. “Buh-bye!” she waved at her husband, who sat across the table from her with a blank look on his face.

“And then?” I asked

“And then, I’d be able get someone younger and richer. After 15 years of marriage to him, and always being on a budget, it’s time for an upgrade.” Her husband shrugged and looked like a deer in the headlights.


“So who do you have for me?” The voluptuous, tawny-skinned Chablis had cornered me at a Watermill soirée, her ample décolletage on full display. It’s not that I really know Chablis, mind you—more that I know who she is from reading third-tier Hamptons giveaway publications in the bath, magazines in which she is shown artfully affecting the same pose (and demented smile) at random store openings, vague charity events and suspect cocktail parties, often in the company of faux reality stars and the like. Needless to say, women like Chablis are highly entertaining and good material.

There’s something palpable in the air, a sense of overt longing and envy that has seeped a layer below the 1 percent to the very affluent but not quite super rich.

“Aren’t you married?” I asked (not that I know her husband either, but I have seen the low-budget ads for his eponymous company, which sells porcelain thrones [not real business] ).

“I’m so out of there,” she said somewhat defiantly, applying cotton-candy gloss on her inflated pillow lips.

“Oh, that’s too bad,” I shrugged, not knowing what else to say.

“Where have you been?” She ran her fingers through her double-processed platinum hair and extensions. “I thought you know everything, Rich!” She licked her lips suggestively. “Anyway, Ira [not real name] sold me a bill of goods and isn’t rolling in it like I thought, so I want more and now I’m going to get it. I want someone handsome, sexy and rich. So, who do you have for me? I heard you fixed up the so-and-so’s (a divorced and happily dating couple). He’s a Euro cutie. I want that!”

Oh, I didn’t realize you are friends of theirs.”

She paused. A friend of my friend is…um…friends with them,” she said unconvincingly.

Well, it’s not like going into Bergdorf’s and picking out a Gucci bag, my dear. Or ordering up a Tesla. What are you looking for?” I humored her, eager to hear her game plan.

“It’s not what I want but what I desereve. I see these women married to like, billionaires, and I want that.” She slurped her rosé champagne. “Why should they have it and not me? After all, those women don’t have the twins.” She arched her back.

“Chablis, very often in a first marriage, the ladies met and supported the husband while they were first starting out. They arrived when there was very little money, and they put in their time, raised the family and believed in them.”

“Well, I believe in Hundy’s” she laughed, “and, I have other things to offer.” She had a convenient wardrobe malfunction, as her skimpy Versace burst open at the seams.

“Sometimes, the twins just want to say hello,” she shrugged.

“Clearly. Chablis, are you sure you made the right choice by leaving Ira? It’s not that easy out there the first or second time,” I cautioned.

“Third,” she said matter-of-factly.

“Busy girl.”

“That’s my motto: ‘Get busy.’ Anyway, I’ll take one of your tall South Americans or Euro types that own oil wells. Or something cash…um…producing,” she said blankly, her taut eye job producing a question mark on her forehead.

“I’ll keep you in mind, although I don’t have a stock room of rich bachelors. I’m actually an ad man and author, not a professional matchmaker.”

“Even better. You know all the rich guys through biz. But they have to have great abs, be adventurous and—”

“…And be funny as [famous comedian and Hamptons resident]?” I offered.

“How did you know?”

“I think it might be best not to have a list.”

“That’s what my mother always says.”

“Anything else you want?”

Well, it’s not like I won’t take someone fugly. As my grandmother used to say, ‘Sometimes you have lay down and spread ‘em for old Glory.’ ”

She downed her flute and walked away, tripping over her Manolos.


There’s something palpable in the air, a sense of overt longing and envy that has seeped a layer below the 1 percent to the very affluent but not quite super rich. Once satisfied with their lives and lot, some in this group (whose own parents were happy owning their own home, appliances and yearly vacations) vocally want their share and quick and are willing to do whatever it takes to get it. Divorces are occurring because of it; Ponzi schemes are created for it; friendships have become strained as social leap-froggers jockey for position. Financial and social disillusionment have rendered bad behavior more obvious and choices more overtly cynical. Couples that would have had long-term marriages in years past now choose not to weather the storm. They don’t just want out; they want up. Now.


‘I  think it’s all about lifestyle envy.” Ruby Flame and I were chatting at an evening event at one of the Hamptons’ new statement beachfront manses

‘It’s not just about relationships and the newest designer bag. It’s a lifestyle issue. It’s how people live, and the way it makes other people feel.’

“Truffle pizza?” one of the servers offered. “Grapefruit and Tito’s vodka shot?”

“It’s not just about relationships and the newest designer bag. It’s a lifestyle issue,” Ruby continued. “It’s how people live, and the way it makes other people feel. I’m a very secure person, so I’m happy for people who live this way and happy to be invited, even though it’s not my particular lifestyle.”

“Cauliflower risotto?” The waiter pointed to the buffet.

“I would never, as an example, be with someone I don’t like just for the lifestyle. I’d rather be alone. And have been,” she mused. “However, I do understand why people do it, and I know both women and, yes, men, who have sacrificed their personal relationships for ‘The Lifestyle.’ ” She smoothed her Proenza over her toned figure.

“And when do they look for the upgrade?”

“I think certain people test the waters and then realize that they are no longer 25 without children and that, aside from a fling, at the end of the day Mr. Fabulous isn’t going to commit to the upgrade, so in the end they decide to stay.”

“What about those that cut bait to get the upgrade before they find someone?” I asked.

“I think if they are confident and secure it’s fine, but not everyone finds what they are looking for. I’m sure it’s a difficult realization once they decide to make that move and they can’t find an upgrade.” Together we made our way to the buffet, passing a divorcee flirting simultaneously with both a bartender and a single private equity guy.


Our SUV negotiated the potholes as Business Partner and I caught up on his trip to St.-Tropez while trying to get to our new business meeting on time.

“It was great to go, but I am happy to be back,” he said. “There are just so many five-hour lunches one can take.” He laughed, adjusting his Tom Ford Aviators. Biz Partner is president of NSGSWAT and lives with his partner downtown.

I told him of my latest modern anthropological theory. “Searching for the upgrade…,” he mused. “It mirrors what happens in the straight world. There are just some men who want to be taken care of. And they know time is limited while they still look great and need to lock it down”

So they’re obvious about wanting the upgrade?” I inquired.

“One-hundred percent. They’re looking for the sugar daddy, literally, so they can fly private and live the fabulous lifestyle. They will say, ‘I need to find a rich one now,’ even if they have a boyfriend. ‘This (the body and face) isn’t going to last forever.’ I personally can’t understand it because I love to work, but they really want someone to just take care of them.”

“So how do they do it?”

“The new way is to post seemingly unassuming shirtless pictures of yourself on Instagram. It’s almost like respectable porn. People follow you and get to see you and your great body in suggestive situations and poses. Many end up using their Instagram as bait to land a rich one. Or at least become ‘Insta-famous’ to get invited to really good parties.” On his phone, he pulled up an image of a buff fellow in a provocative, shirtless pose—ostensibly a travel photo.

“That’s an interesting ploy.”

“And this is a substantive person with a real job.”

“Really?” I raised both eyebrows.

“Well look, you can’t blame him…He just wants to lock it down while he still has this.” He framed his face with his hands as though he were Voguing.


Our Lady of the East River was receiving after a lengthy hiatus. Her houseman showed me onto the terrace, offered me a glass of Sancerre and silently placed a gorgeous platter of airy white French cheeses on the wrought-iron table. Our Lady emerged in vintage Pucci, her saucer-sized sunglasses offsetting her perfect blonde coif.

“Dahling, I have missed you.”

‘The men are vile. Boastful and vulgar, only able to talk about the latest deal or what they acquired. There is no more art to conversation. In my day, these people would only have been accepted only by gangsters and show people.’

“You’re looking très chic, as usual. Lovely to see you in good form,” I responded.

“I assume you want this old woman’s naughty opinion.”

Young woman,” I said. “And yes I do.”

“It’s an old story that resurfaces every few decades.”

“How so?”

“When I was a young deb, there were a few men in our circle who succumbed to the charms of actresses or showgirls, all who were all looking for their meal ticket.”

“Actually, the story is more about people who want an upgrade ‘midstream’ in their relationship.”

Oh yes, I understand now,” she replied. “The story I have isn’t about a woman but a gentleman I knew many years ago. He was matinée idol, good-looking and was known as a yo-yo.”

“A yo-yo?”

“You know, going with women and men, dahling. I know it’s an old term. He married a gal I knew who was a somewhat attractive but dour heiress. Positively humorless. One day they find her trust is no more, and she has to cut off his allowance. She cancels the polo and the clubs. He, of course, was livid and went about actively looking for a replacement as he was not cut out for a desk job.”

“Did he find it?”

“Yes, he married [an older socialite]. The overt nature of his quest made it somewhat scandalous at the time.”

“And why did Madame D’argent marry him?

“The men always have it easier. I always say it’s quite unfair. While he was wasn’t the brightest bulb on the Christmas tree, he was handsome, had good manners and was known to be quite well endowed. No one looked better in a white dinner jacket. The women were lining ‘up, old and young’ alike. Eventually, I heard she divorced him, and he ended up broke with an older boyfriend…It was quite a sad ending actually. The last time I saw him he was downing cocktails at the bar at the Marbella Club.”

“Do you see this trend today?”

“Dahling. It’s everywhere. It’s all these people from New Jersey who want la grande vie and think buying a (coveted luxury bag) on credit is the answer. The girls I see at the charity board meetings were just answering phones last month before running off with the boss. It’s all so pedestrian. No one is memorable. The new money wives all look exactly the same. I have a hard time telling one from another. It’s ghastly. And don’t get me started on the men!”

“Please do.”

“Well, since you ahsked “ She grinned and sipped her martini. “The men are vile. Boastful and vulgar, only able to talk about the latest deal or what they acquired. There is no more art to conversation. In my day, these people would only have been accepted only by gangsters and show people.” She gave a slight gasp.

“Mauricio dear, would you mind a refill?” She pointed to her glass.

“What do you think about them wanting an upgrade?”

“Dahling, if I was married to any one of them I would have gotten an upgrade a long time ago.

You mean the money would be important?”

“Heavens no! If I married someone run of the mill or boastful, I would never have stayed. I would rather die broke and happy with a man who could make me laugh, than rich and bored to tears with a vulgarian! That’s the upgrade. More fromage, dear?”


Montauk continues to evolve into swarms of people in search of St.-Tropez–style moments. We were lunching at the fabulous and chic Duryeas at a friend’s late summer birthday soirée.

“I used to come here as a kid, when it was only fisherman,” my lunch partner remarked, looking at his carbonized Rolex.

‘Dollar Bill was having a party on his boat in Sag, and we met and haven’t left each other’s side.’ Chablis caressed his hairy forearm and solid gold Rolex. ‘Cancel my order,’ she winked at me. “I got a live one.”

“It reminds me of a beach club in Europe!” I agreed. Around us, girls adjusted their Calypso cover-ups as cool top-noted French waiters poured magnums of Cotes de Provence.

“Richard! I cannot believe it!” I blanched as a scantily clad Chablis sashayed over to our table in white translucent short shorts. “I want to introduce you to my new boyfriend. You know Dollar Bill,” she exclaimed.

“Chablis, what a surprise,” I said. “No, I haven’t had the pleasure.” I extended my hand to her swain, who flashed Chiclet-sized laminates and stroked his chest, his shirt unbuttoned to the navel.

“When did you two meet? I only saw you two weeks ago.”

“Dollar Bill was having a party on his boat in Sag, and we met and haven’t left each other’s side.” Chablis caressed his hairy forearm and solid gold Rolex. “Cancel my order,” she winked at me. “I got a live one.”

“We’re taking the boat to a party in Sag, and then we have a party in Bridge and then a dinner party at so and so’s.” Dollar Bill  broadcast their schedule to no one in particular.

“Come on, babe. We don’t want to be late.” He pulled Chablis by the arm as she air kissed us goodbye.

“How do you know her?” Hedge Fundress sniffed, as if Chablis were old sushi one overlooks in the fridge.

“She cornered me at Publishing Princess’s party in Watermill, as she was desperate for a rich boyfriend.”

“Well, my girlfriend used to date him, if you can call it that, since she paid for everything. Word is that both of them are looking for the upgrade. Dollar Bill lost 75 percent of his money when the MLPs hit the skids, and the other 25 percent went up his nose. My friend told me that Dollar Bill thinks Chablis is rolling in it due to her settlement with Ira, and Chablis isn’t smart enough to read the tea leaves that everything with Dollar Bill is rented: the Porsche, Hamptons house and studio apartment in the city.” She smirked. “Both spray-tanned poseurs looking for the upgrade, thinking the other one has it.”

“It reminds me of Dana’s favorite O’Henry story—a Hamptons version of The Gift of the Magi,” I mused.

“Poor Chablis,” a fellow reveler said out loud as she walked along the dock to Dollar Bill’s rented boat. “She’s a hot number, but he’s nothing more than a gigolo.”

“Poor Dollar Bill,” another woman at the table chimed in. “She will eat him alive and pick what’s left off the bone.”

At that moment, I saw Chablis and Dollar Bill board a rented boat, speeding off to their next social destination.

“So what do you want to do tonight, honey?” Dana massaged my neck. “Go with Chablis to a million parties?”

“I’d rather walk barefoot on broken glass. I just want to grill some salmon and stay in and veg.” My mind was reeling at what we’d witnessed and heard.

“Sounds like the perfect evening to me,” Dana agreed.

We thanked our hosts for the lovely afternoon and made our way to back to our home and children, with the knowledge that those in search of an upgrade often end up with nothing more than…a downgrade The ‘2 Percent’ Aim to Make the Move to Elite Status