Skip to content, or skip to search.

Skip to content, or skip to search.

Where the Boys Are!

Inspired by Hollywood, increasing numbers of New York women are aiming younger -- and scoring higher.


Madonna, 43, and husband Guy Ritchie, 33.  

When Jessica first met Nick at a friend's party, it felt like the perfect fit. She was a divorced former model, now working for a white-shoe law firm, and though he was vague about what he did for a living, the chemistry was there. She thought he was around 30, and he made the same assumption about her. It wasn't until three months later that they discovered each other's actual ages. He was 24 and she was 37.

"When I found out how old he really was, I wasn't sure I even wanted to be friends," Jessica says now. As it turned out, though, the thirteen-year age barrier wasn't as daunting as she thought: Today they are married and raising a 3-year-old in their Upper West Side apartment. Still, Nick can't forget her first reaction when she learned how young he was. It was like a brick wall going up, he says.

Now, nearly a decade after they first met, the gap seems, if not normal, at least far more acceptable than it once was. (Although Jessica still avoids discussing her age with her mother-in-law.) And judging from what's been going on in yoga classes, Soho lounges, and the celebrity-gossip pages this summer (not to mention movie screens), the long-standing taboo against older women dating younger men is finally losing much of its primal power. New York women in particular are openly dipping into lower age brackets in numbers that would have been unimaginable in the past.

Thanks to their increasing financial independence, women are freer to consider romantic options once filed under INAPPROPRIATE. And thanks to the ruling gym and fitness craze (not to mention Botox and plastic surgery), they hardly look their age anyway. "Women have to stop thinking guys under 35 are not an option," says Jessica, "or that it will make them look foolish."

Take Justine, a makeup artist in her mid-forties who first started dating younger men last year, after a twelve-year relationship with a man twenty years her senior. She had previously dated only older guys, but now the ones she met were either attached, too involved in their work, or just plain unappealing. Luckily, she noticed a strange thing happening: Many of the men who approached her were half her age. Her Chanel boots and leather pants might have had something to do with it. And her devotion to Pilates. When a friend had a costume party, she says, "the theme was 'Bond girl,' but I just showed up in my usual Friday-night outfit, and everyone said I had the best costume in the room."

At another friend's birthday party, a restaurateur named Paul, who was only 34, kept wanting to dance with her. "Every time I turned around, he was there," she says. They danced, they drank champagne, and she kissed him good night, but the next morning she congratulated herself for not giving him her phone number. Then the phone rang at work.

Justine tried to get rid of him by insisting she was too busy to talk. "Can I call you at your other numbers?" he asked.

"Which numbers did I give you?" she shot back.

"All of them," he said. And with that, Justine gave in -- at least for a drink. "I wondered if my subconscious wasn't trying to tell me something," she says.

Then came the orchids. And the caviar. Paul talked about their future together. "I found myself getting involved in the dreams I thought I had passed," she says now. "He re-instilled in me the sense that it's not over yet."

In the past, when people thought of older women with younger men, they usually pictured a widow of a certain age with a mother-obsessed gigolo, or a past-her-prime movie star with a muscle-bound stud of ambiguous sexuality and unambiguous greed. But the new dispensation isn't about Leona Helmsley or Mae West. It's about Madonna, 43, marrying Guy Ritchie, 33; or Sandra Bullock, 38, who's seeing Ryan Gosling, seventeen years younger. Daryl Hannah, 42, has been spotted around Paris and London with David Blaine, 29. And Janet Jackson, 36, made "Page Six" two weeks ago by canoodling with Justin Timberlake, 21.

Message boards on MSN and iVillage, and sites like, are alive with gossip and advice on the subject. And Hollywood and Broadway have taken note of the cultural shift. For the past four months, Kathleen Turner, 48, has been sleeping with 24-year-old Jason Biggs eight times a week at the Plymouth Theatre in The Graduate. Meanwhile, at the multiplex this summer, there's been a mini-epidemic of older-woman-younger-man couplings: from Diane Lane's dangerous liaison with a younger Olivier Martinez in Unfaithful to Bebe Neuwirth's surprise fling with her best friend's 15-year-old stepson in this month's Tadpole. (Not to mention Senator Amidala, whose older-woman-younger-man affair with Anakin Skywalker is at the heart of Attack of the Clones!)

In August, 33-year-old Jennifer Aniston will hook up with 21-year-old Jake Gyllenhaal in The Good Girl, making Gyllenhaal the new poster boy for OWYM relationships, since he's also the object of 39-year-old Catherine Keener's affections in this month's Lovely and Amazing.

For New Yorkers, though, the summer's most compelling cultural signifier isn't a film or a play. It's Candace Bushnell's surprise July 4 marriage to New York City Ballet dancer Charles Askegard. The Nantucket affair merited a front-page "Sunday Styles" story in the Times, but what had everyone talking was not that the author of Sex and the City had finally ended her famously enviable single life after only eight weeks of courtship, or that her most recent ex-boyfriend flew in from London for the occasion. The surprise was the age difference between the 43-year-old bride and the 33-year-old groom.

Current Issue
Subscribe to New York

Give a Gift