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Authors: Richard Kirshenbaum,Michael Gross

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III.

UPTOWN PROBLEMS

8. DATING TIPS FOR UPTOWN DIVORCÉES

Middle-Aged Millionaires Just Aren’t That into You

I WAS AT MY USUAL BANQUETTE TABLE
at Cipriani catching up with my dear friend and fellow gala charity chair, the Impossibly Blond and Glamorous Socialite. She looked up, over her grilled salmon and leeks.

“Do you have anyone for my friend Leanne? Her divorce just became final.”

I recalled a lithe brunette who looked good in Lilly, making the rounds of the Hamptons charity cocktail circuit along with her pint-size now-ex-husband.

“Is she realistic yet?” I asked.

“I think so.”

“Good.” I sipped my Bellini.

My friend and I, while an unlikely matchmaking duo, have been informally setting up divorced friends and “children of” on the Upper East Side for years, and with solid results. We always say we should charge a commission for our dating service, but that temptingly profitable idea would be too déclassé.

Our biggest challenge, time and again, is matching up middle-aged divorcées in the “pre-realist” stage, who have not realized that they have a choice of sex, money, or a warm body—but not all three in the same package.

“How did she make out in the divorce?” I asked my friend.

“All I know,” she revealed, “is that the husband made her include her Birkins as a part of the settlement.” She added: “At the
current
retail price.”
Bien sûr!

“She most likely will want the money, then.” I paused, Rolodexing in my head the range of the newly wed and nearly dead. As I gave the hand signal for the check, I thought of a few years’ divorced friend who could use a chatelaine for his manor, and Leanne was an ideal prospect.

“Oh yes, I think I have a good old-fashioned septuagenarian billionaire in Palm Beach for her. Not exactly scintillating, but his real estate portfolio has a personality all its own.”

“Perfect,” she said. “I’ll call her with the good news.”

A few years back, I cowrote a fairly well-known relationship book for women called
Closing the Deal
; the premise was that two married men’s advice could help turn single women into
deal closers
. While we had no formal training as relationship experts, we just implicitly understood that if women understood men better, they’d have a better shot at closing the deal. Knowing your audience is always key, whether personally or professionally, and we offered advice on topics from hygiene to foreplay.

Where most rich divorcées fail is in assuming they can replace their husbands with a newer model pretty much like the old one. Sorry to say, this tends not to be the case. Most of the time, the divorced well-to-do male is not looking for his equal, but rather for a sexretary from the Midwest, preferably without an opinion. As one recently divorced hedge funder told me: “Being married to a smart, opinionated woman is work! Now I just want tits on a stick, a blond wig, and someone to tell me I’m great when I get home.”

Women who take a tough line often wind up lonelier for it. At a political fund-raiser, my wife, Dana, and I were chatting with a well-regarded financier’s ex-wife, who clearly exhibited pre-realistic dating tendencies. She laid out her requests like the Marshall Plan: “My age or younger. I won’t date a geezer. Richer—the richer the better. Sexy. OK, let’s just cut to the chase: my ex if he had abs and a personality.”

“Don’t you think you shouldn’t have a list?” Dana asked innocently.

“That’s for
other
people,” she snapped.

She is still on the prowl.

Far more successful are those who focus on just one wish-list item, for instance sex. Assuming the woman is not completely devastated, pulling a Mrs. Robinson is a popular rebound maneuver once the lawyers have retreated and the paralyzing legal battle becomes a bitter memory.

Seducing younger men works out well for one rock star’s ex-wife I know, who prefers bedroom sizzle over an eight-figure net worth. Over lunch at Da Silvano, she professed to not care about money, which apparently is a British thing. (Not that she doesn’t have an unlimited budget for couture.)

“I’m English,” she said. “We don’t
like
money. It’s vulgar, never to be discussed.”

“So you’re not interested in a man with money?”

“Not at all. I’m into spontaneity. The younger the better, twenty-five to thirty. It’s a win-win. They’re in awe.”

“Of … ?”

“My experience.”

Notable hookups for such divorcées include affairs with French or Italian baristas, a Roman Casanova who preys on the newly divorced (despite good tailoring, he’s overcommitted and overdrawn), and the occasional Moroccan rug salesman. (“She got a ride on his flying carpet!”)

More common are the standard-issue service-industry providers: the omnipresent trainer, manny, male
or
female yoga instructor, Hamptons carpenter, contractor, driver, plumber, beach club attendant (for real Mrs. Robinson cred), and tennis pro. Since trainers are allowed an all-access pass to the family compound, they frequently help their clients lift and separate in different areas during the a.m. and p.m.

“Why is the trainer the obvious choice?” I asked a leading member of the clergy who confirmed the trend.

“I think it’s accessibility and availability,” he said. “If there’s a man close by, it’s affirmation, and it’s exciting for them. I have seen women relatively happy for a period in this arrangement.”

When finances aren’t important—but sex isn’t either—another option is “the warm body,” a common choice among the older set that also has its appeal for the career woman.

The warm body tends to be the straight man’s version of a walker: he may be dull as a month-old razor, but he provides an audience, especially to women who really want to do all the talking.

“Having a companion is nice. I already took care of a man once before,” a Madison Avenue matron remarked, opening her Bottega Veneta wallet and plucking out her ATM card. “Dinner, a movie, a cruise, prop him up in a chair, and away we go.” She smiled. “He doesn’t say much, but I find he hangs on my every word.”

Even younger women agree. “I just need him to change a lightbulb now and again,” said a friend.

“Sex?” I asked.

“Whatever.” She shrugged.

Not every divorcée, of course, is in a financial position to while away her days with the cabana boy (or his friendly, benign father), and some must resort to mercenary tactics to avoid expulsion from the golden triangle of Park Avenue, Sagaponack, and St. Barths.

“I wake up in a cold sweat that I’m only going to be able to afford a
white
brick building on Fifty-Seventh Street or a four-bedroom in the Financial District,” my wife’s friend lamented outside spin class. “Getting divorced is bad enough; the real estate downgrade is the final straw.”

Contrary to popular misconception, just divorcing a rich man doesn’t necessarily leave one set for life. I put a call in to an old friend who has a reputation as one of New York’s toughest divorce attorneys. One of his three assistants put me through.

“You next?”

“Sorry to disappoint,” I joked. After brief pleasantries, he told me business was booming now that couples can almost afford to part ways, and he laid out the economics.

“OK, let’s be clear; if the woman has the real money in the relationship, she can do whatever she likes.” That said, that’s not
most
women.

“So let’s just say you’re a relatively affluent couple in the twenty- to twenty-five-million range. By the time the lawyers take their eight-figure slice and the mortgages are paid off when the residences are sold, she might end up with a six- or eight-million-dollar check. It sounds like a lot of money, but that’s it for her, unless she marries again. A conservative three percent on six million—one hundred and eighty thousand dollars a year—is her clothing allowance from her former life.”

“So then what happens?”

“The ones with younger kids get alimony and child support. But the smart ones end up with the best sixty-year-old they can find.”

“And if they don’t?” I asked.

“There’s always Boca Raton,” he said.

I was heartened to hear one last and affirming category surfacing above Fifty-Seventh Street. These are the women who, empowered by divorce, want a real relationship centered around their kids.

A leading divorce consultant (a businesswoman who acts like a general contractor for people going through the process) had this to say: “There are those women who want a man to take care of them. Then again, there are those women who say, ‘I can do this,’ and just want a nice, normal guy who loves kids. Someone to provide their children with a moral compass.”

“So how do people meet guys like that?” I asked. “Do they fly coach or business instead of first?”

“If they start working again, they might meet them in the office, or at a kid’s baseball game, for example. There
are
healthy relationships out there,” she said. “From what I’ve seen, the women who get jobs afterward meet better men than the ladies who continue to lunch.”

I have one successful female friend who met and married a very nice family guy who was moderately successful himself. The one prerequisite was a makeover: better shoes, a nice belt, and no dad jeans.

I was getting the financial papers on Sunday on Lexington Avenue when I ran into an acquaintance, a high-end real estate broker who specializes in white shoe co-ops; he was listing an exclusive Park Avenue 12 with southern exposure.

“It just came on the market. You know death and divorce are the best things about real estate in this city,” he said darkly.

“Whose apartment is it?”

He mentioned a high-profile couple who had recently split.

I remembered the fabulous layout. “She doesn’t want it?” I asked.

“She can’t afford to buy him out.”

“Too bad.”

“I know. If she’s smart, she’ll get down to business and land an oligarch for papers,” he joked. “You know some of these women are like the real estate themselves. They come on the market, too many showings, sit too long without a bid, and then the product gets burned.”

Luckily, no such fate awaits two newly minted and very eligible divorced people I introduced in February at our annual Valentine’s Day Jazz Brunch, where we served up a torch singer and made-to-order omelets to a variety of guests. Both parties have interesting careers, in addition to having children.

“You two should know each other.” I literally hip-checked the lanky European businessman into view of my friend, a lovely entrepreneur. A friendship and fireworks ensued. Perhaps they had the advantage of finding each other when they were both considered fresh listings, new to the market, in prime Fifth and CPW locations. They snapped each other up.

A thank-you text appeared on my phone just yesterday revealing summer plans for the new couple: first a romantic trip to Anguilla, then two weeks in Cap Ferrat. Not only is love in bloom on two continents, but the very best thing is that in spite of it all, they won’t have to move to Florida.

9. THE HIGH FLIERS

Uptown Pill-Poppers Struggle to Hide Excesses from the Kids

SPRING BREAK FOUND US
fleeing manhattan for the glorious Los Angeleno sunshine, palm trees, and alfresco lunches by the Beverly Hills Hotel pool. We were ensconced in the famed Howard Hughes bungalow, which I am sure has withstood its own share of vibrations over the years. Still, nothing prepared us for the 4.9 earthquake that interrupted our reverie and shook us out of bed at 6:30 a.m. Like a fool I called the front desk for confirmation. “Yes, Mr. Kirshenbaum. That was indeed an earthquake.”

The next day, after a sleepless night, we ran into myriad New York families, all on spring break, having McCarthy salads by the pool, fiddling with the romaine and cheddar. “Aftershocks can be worse than the quake,” I worried aloud to anyone who would listen.

“Don’t worry,” my friend’s platinum blond wife said, retrieving her pillbox, implants immovable in her string bikini top. As her toddlers pranced about, she opened what seemed like a veritable pharmacy in her designer clutch.

“A little Xany will do you good,” she said, picking around in the compartments. “Let’s see, I have Valium, Xanax. Oh, those are the antidepressants. Wait, are those the Klonopin or the Zoloft … ?” she pondered.

“A cosmo and Molly and you won’t remember a thing,” she offered. “Even if the big one comes.”

Having grown up in the “Just Say No” generation, afflicted by fear, guilt, and propaganda, it’s strange to see so many New York parents smoking, popping, and snorting as soon as their kids are counting sheep.

“It’s the ’80s again,” a good friend said at a recent party, inhaling a funny cigarette and passing it along.

“Why’s that?” I said, taking in the duplex transformed into a dance party.

She gesticulated above the din and deejay spinning electronic dance music. “Let’s say you’re at a party and it’s a five. By smoking or drinking you already elevate it to a six or a seven. Time is valuable. All I have to say is:
elevate your party level for better times, baaaby
.”

“Well,
they
certainly are,” I said, pointing to two married women (to men) I knew who were gyrating and making out in the corner.

“That’s my point. You don’t feel old, you feel free. You’re having a renaissance,” she said as she toked.

“Any downside?” I said, taking a Jell-O shot.

“I haven’t heard any bad reviews.” She shrugged in her vintage Halston halter. “Honestly, I want to go out there and have a great time. I want to be wasted, entertained. I just want to fly high and have fun. Take the edge off,” she mused.

“The cause for all this fun?” I probed like a proctologist.

“It’s a midlife crisis. Lots of
rich girls
doing coke, Mollys, and edibles behind their husbands’ backs.”

“And your husband?” I asked, wondering what the straitlaced banker would think.

“We don’t have that kind of relationship,” she said. “I’m honest.”

“Honest?”

“I said to him, you’re missing out. If you want to go out and have to deal with all these people
unmedicated
, that’s your issue.”

After I got back from LA, I was catching up with a friend after his family’s ski trip to Aspen.

“How was your trip?” I asked.

“Half of New York was there,” he said. “It was a crazy party.”

“How was the skiing?” I asked.

“Everyone in Aspen was high. They were bumping off trees on the mountain like pinball machines. You cannot believe the dispensaries out there. By the end of the trip, the whole town was sold out. People were bringing back the infused gummy candies by the garbage-bag full.”

“Are you serious?” I asked.

“People were eating those gummies like sunflower seeds. They were whacked.”

“What do you think about it all?”

“Look,” he said, asking his assistant to bring him a double espresso, “it’s people trying to hang on to their youth. You can get wasted when you’re in your forties and fifties but it’s kind of sad when you see people in their sixties who are sloppy. So you might as well do it while you’ve still got it going on.”

Our first weekend back from the left coast saw us at a dinner party in an elegant Normandy pile in Greenwich. It was a well-heeled and conservative crowd, which prompted me to ponder whether drug usage had made its way to suburbia. My dinner partner, a vivacious and convivial gal, seemed taken aback by my line of questioning.

“No. None of my friends do drugs here,” she said with distaste. “They only drink. I think New York is just a faster crowd.” She eyed me suspiciously as she took a spoonful of crème brûlée.

“I’m sorry, I didn’t mean to offend you and ask if you were partaking. It’s just that I am writing an article.”

“Yes, I’ve read some of your pieces. You seem to know the most ridiculous people.”

“That I do.” I smiled.

“Wait.” She turned to me in a discreet fashion, as if offering up the tidbit like a peace sign. “I think I have something for you. Do you know how all these women stay so thin?” she whispered, as if giving up the secret location to the Maltese falcon.

“How?” I leaned in.

“They take their children’s ADD medication. It’s all speed, suppresses the appetite.”

“I was sober for a decade,” a fellow charity board member and fairly new acquaintance revealed over lunch at Bill’s. “My drinking was honestly the cause of my first divorce.”

“First?”

“I’ve also been married multiple times. Runs in the family.”

He asked the waiter for a whiskey, neat. “My mother was an artist, a socialite, an alcoholic, and, honestly, a drug addict. I was shipped off to a different boarding school with each new husband. That said, she had great style.”

“All those schools,” I sympathized. “That must have been difficult.”

“It’s all a blur between the beer and the bong hits.”

“Do you and your friends still do drugs?”

“Well, everyone on the North Shore and in Palm Beach is friendly with the drink. Drinking is part of the culture—cocktails before dinner, roadies at the [
über
exclusive North Shore golf club], bloodies at the [fortresslike Palm Beach private club].”

“So no drugs?”

“Let’s just say I’m trying to
teach
myself to do coke more. I bought a spoon.”

“Teach yourself? Why?”

“I’ve gained so much weight from the beer and vodka, I’m starting to resemble a keg.”

The next week, I met a golf buddy at Sant Ambroeus for a fluffy egg white omelette and espresso. As we were catching up, he said that his twelve-year-old son had walked into the apartment unannounced and smelled the marijuana.

“That’s not cigarette smoke. Is that what I think it is? That’s
illegal
,
Dad
!!!”

My friend tried to explain that adults sometimes relax in other ways.

“Who are you buying this from?” the son lectured. “These are bad people. Dad, do you want to go to JAIL?” he pleaded.

A similar story was relayed to me as well when a friend’s daughter came home early and caught my friend, a conservative Madison Avenue private equity guy, smoking weed. The daughter shrieked, “Dad, what are you doing?” The father turned white and said—and I quote: “It’s not mine, I’m just holding it for a friend.”

The digital landscape has transformed everything, from book and food delivery to drug delivery.

“In college I used to have to go to some grungy park and meet ‘the guy,’” said one of New York’s high fliers. “Now it’s just a text away. It’s like when I first moved to New York and I could order in moo shu chicken. I thought having a doorman and ordering in takeout was the ultimate luxury. Now I’m getting the weed delivered to my doorstep. It’s the next level of delivery!”

“I felt that way about Fresh Direct a few years back,” the wife interjected, “and our dealer is very stylish. You should see, he’s all in Dolce. In fact, I asked him where he got his blazer and told him to pick one up for Mark (not his real name) in a size forty-two.”

“Oh, I love that blazer. I didn’t realize it was from Yves (not his real name).”

“Now he’s adding personal shopping as an extra service,” she said admiringly.

“I have a different theory,” Respected Uptown Therapist revealed in his office.
Why do they all love Danish Modern furniture with nubby fabric?
I wondered.

“There’s an enormous amount of social pressure in New York City. To be thin, to be beautiful, to be rich and successful.” He stroked his Freudian goatee. “There’s a term, ‘relative deprivation.’”

“Meaning?”

“You may have it all but you are relatively deprived compared to someone who has much more than you have. And then it’s about appearances.”

“I call it the press release,” I offered. “Don’t forget everyone has perfect children as well who are all
geniuses
and
savants
.”

“With all this pressure, the drugs, drinking, and partying are the pressure valves. The more pressure, the more need for release.”

“Perhaps that’s why it’s happening more in New York City?”

“It is undeniable that it is more stressful in the city. When you’re doing drugs, you forget your problems. I see a lot of wives doing drugs to escape their husbands’ reduced bonuses.”

“Sounds like high school all over again.”

“Yes. Even down to the rich popular kids. Only now they’re parents.”

Just this week I woke up in wrenching pain and headed to the dentist.

“You have a fractured tooth and it needs to come out. Most likely you’ll need an implant.”

I always say toothache is as bad as heartache, but not nearly as romantic.

“Give me
every
painkiller you have,” I begged. “I also have a business function at six I have to attend.” First came the Novocain, then the crushed Triazolam, then the gas. Two hours later I awoke, numb and swollen and still flying.

“I have one question,” I asked the staff as they helped me to the waiting room. “Do you think it’s OK if I make the cocktails? I have a few people I want to see.”

“I think it’s OK but don’t overdo it,” they stressed.

Dana was in the waiting room and steadied me to the car.

“I really think we need to go home,” she said.

“Absolutely not,” I protested, even though I was a bit unsteady. “I feel great.”

When we got to the Lever House, we entered the party, Dana holding me by the elbow.

“Hi, Richard. So good to see you,” the socialite said. “You look amazing. So relaxed.”

“It’s true,” the editor agreed. “He looks ten years younger. No frown lines.”

What would have been a nice but obligatory cocktail party seemed to pass in a flash with laughs and effervescent conversation. Indeed, I had elevated my party level.

That is, of course, until I woke up bleary-eyed, the next morning.

“Daaaad.” My teenage son tugged at my blanket, as I lay supine in bed. “I really think you need to stay in this evening and get some rest. Enough is enough.”

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