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Our editorial content is not influenced by any commissions we receive. As long as men and women have existed, men have desired women younger than themselves. All of biology and society is tilted in this direction, whether it's the fact that men remain sexually potent far longer than women do or the squishy idea that men become "distinguished" as years go by while older women look, well, "old. A year later, the two reunited, and on Saturday, the news broke that they again planned to wed, this time in a small ceremony to be held on New Year's Eve at the Playboy Mansion. Let's face it: Hugh Hefner is a freak, in the most enviable way possible.

Harrison Ford and Calista Flockhart Age difference: 22 years.

Jan 12,   We know, we know: Older guys dating younger women is the oldest-and most cliche-story in the book. And while we don't need to go into all the reasons why men of a . Celebrity Cougars: Female Stars Who Have Dated Much-Younger Men (PHOTOS) Admit it, you're curious: If the new millennium has brought anything, it's a generation of women who throw age conventions to the wind and date men of any (and all) ages.

Ronnie Wood and Sally Humphries Age difference: 31 years. Bruce Willis and Emma Heming Age difference: 24 years.

10 Married Celebrities With HUGE Age Differences

Eddie Murphy and Paige Butcher Age difference: 19 years. Age difference: 30 years.

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Annette Bening and Warren Beatty Age difference: 21 years. Billy Joel and Alexis Roderick Age difference: 32 years.

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Kelsey Grammer and Kayte Walsh. Follow ComplexPopCult.

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Dec 15,   15 Hot Celebrity Women Who Are Currently Dating Older Men. By Josh Robertson. Josh Robertson is a freelance writer based in New York City. men have desired women younger than themselves. All. Jul 31,   They all made dating younger men a trend to watch, Leonardo DiCaprio, and Bradley Cooper, just to name a few) while older women face incessant scrutiny. These 14 celebrities prove that dating Author: Michael Beckert. May 31,   The year-old reality TV star and the year-old boxer-turned-model began dating in , a year after Kourt split from baby daddy Scott Disick (who is four years younger than her).

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