What a Girl Wants — If She’s Newly Single in Hollywood
Then there's Madonna, 52, whose taste in men, despite a brief fling with Warren Beatty during her Dick Tracy/Blond Ambition era, always has skewed younger. Her first husband, Sean Penn, was two years her junior.
Living well is the best revenge. So is looking good. Been there, heard that, moving right along. Lately, if you’re a recently unhitched female star in Hollywood, and you really want to stick it to your ex, upgrade to a much hotter rebound guy, one who’s younger (at least younger than the ex) and preferably a male model.
From Diana Hyland and John Travolta in the ’70s, to Cher and the bagel boy, Goldie Hawn and Kurt Russell and Susan Sarandon and Tim Robbins in the ’80s and beyond, to Demi Moore and Ashton Kutcher in the 2000s, older woman-younger guy combos are nothing new in Hollywood. But lately, the guys seem to be getting, if not younger, definitely hotter. Perhaps the recent cougar craze raised the stakes. A few years ago, the must-have accessory was a gay best friend. But that’s so ’00s. These days, newly single Oscar winners — and Madonna — all seem to want their own personal boy toy.
I’d say it’s a welcome development. Women are generally expected to value personality and/or power over prettiness, but why shouldn’t they look for a guy with as many desirable intangible traits as possible in a super-attractive package? If it happens to last forever — or more than a few months — that’s icing. Halle Berry, 44, kicked off the recent trend with the 10-years-younger French-Canadian model Gabriel Aubry, whom she began dating in 2005, after splitting with her ex-husband Eric Benet. Though Berry and Aubry recently broke up, she got a genetically blessed daughter, Nahla, 2, out of the deal.
Then there’s Madonna, 52, whose taste in men, despite a brief fling with Warren Beatty during her Dick Tracy/Blond Ambition era, always has skewed younger. Her first husband, Sean Penn, was two years her junior. She had eight years on Carlos Leon, the father of her daughter Lourdes, 13. And Guy Ritchie, her second husband and dad to her son Rocco, 10, was a full decade younger than Madonna. Her current rebound guy is young enough to be not only her son, but the kid of all her exes as well. Early twentysomething Brazilian model Jesus Luz was still in diapers when Madonna was stirring up controversy for messing with stigmata, kissing a black saint, and dancing in a field of burning crosses in the “Like a Prayer” video, and donning her first bullet bra.
Meanwhile, Susan Sarandon, 63, who broke up with Tim Robbins, 51, last fall after 23 years and two children together, reportedly has been spending a lot of quality time with 31-year-old Jonathan Bricklin, with whom she co-owns the New York City ping-pong club SPiN. Others who have gone looking for a new love outside of the modeling field: Emma Thompson, 51, who followed her divorce from Kenneth Branagh with love and marriage to Greg Wise, 44, an actor, and Reese Witherspoon, 34, who post-Ryan Phillipe spent about two years in the romantic company of Jake Gyllenhaal, 29.
If any star could use a slight injection of youth, it’s Oscar winner Kate Winslet, who won her Academy Award for bedding a teenager in The Reader. She’ll be 35 on October 5, but in some ways, she reads about five years older. (Maybe it’s all those Oscar nominations, or the fact that she’s been playing moms onscreen since she was 20.) Now the twice-divorced mother of two seems to be making an effort to recapture her misspent youth following her split earlier this year with director Sam Mendes, who is 11 years older than Winslet. Her latest flame, Louis Dowler, is young (the same age as the actress), hot, and, of course, a model.
Oscar winner Sandra Bullock, on the other hand, always has seemed younger than her age (46), and, like Madonna, she likes to dip into the fountain of youth. Apart from Jesse James, her estranged husband who is five years her junior, she’s been linked to at least two younger costars, A Time to Kill‘s Matthew McConaughey (five years) and Murder By Numbers‘ Ryan Gosling (16 years). Now that she might be on the verge of negotiating her first post-Oscar film —Extremely Loud and Incredibly Close, a drama costarring Tom Hanks — soon she probably will want to start thinking about dating again.
I’m convinced that she, too, will go hotter and younger. So don’t be surprised if she shows up at the Oscar’s next year on the arm of a stunning model who’s barely old enough to join her for a champagne toast after the ceremony. 
