May-December romances

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Anna Friel and Charlie Heaton: 17 year gap



Tony Bennett and Susan Crow: 40 year gap

Tony Bennett technically met his wife before she was even born. Bennett wrote in his memoir that he posed for a photo with his now-wife Susan Crow’s parents at one of his shows in 1966. Turns out, Crow’s mom was pregnant with her at the time. Little did they know, the Crow’s unborn baby would end up marrying the singer.



Michael Douglas and Catherine Zeta-Jones: 25 year gap

All-star couple Michael Douglas and Catherine Zeta-Jones share the same birthday, so he’s got exactly a quarter of a century on her.



Christopher Knight and Adrianne Curry: 25 year gap

Christopher Knight was hesitant to enter into a relationship with the significantly younger Adrienne Curry. It was a major plotline on “The Surreal Life.” However, he eventually came around as we learned on “My Fair Brady.” Maybe he should have listened to his gut — the pair split in 2013.



Marilyn Manson and Evan Rachel Wood: 18 year gap

Marilyn Manson was known for his shocking antics. Evan Rachel Wood was not, which is why everyone was shocked when the two began dating. She has also been linked to Mickey Rourke. 



Calista Flockhart and Harrison Ford: 22 year gap

This subdued Hollywood pair seem to be a perfect fit despite a large age gap.



Cameron Diaz and Justin Timberlake: 9 year gap

Despite their age difference, Cameron Diaz and Justin Timberlake shared a lot of interests and hobbies. Like surfing. And golf. Sadly, it wasn’t enough to sustain them. Timberlake is married to actress Jessica Biel and Diaz is married to Benji Madden.



Megan Fox and Brian Austin Green: 13 year gap

The proud parents of three boys met on the set of “Hope & Faith” when Fox was 18 and Green was 30.



Anna Nicole Smith and J Howard Marshall: 63 year gap

The skeezy marriage between the late Anna Nicole Smith and J. Howard Marshall – she was 26, he was 89 – is a May-December story for the ages (but not for all ages).

(AP Photo)


Tom Cruise and Katie Holmes: 17 year gap

Maybe it was the age difference that caused their split?



Woody Allen and Soon-Yi Previn: 34 year gap

Woody Allen and Soon-Yi Previn. The marriage of Woody Allen, 73, and his once-upon-a-time-sorta-step-daughter Soon Yi Previn, 38, takes the prize of most disturbing May-December romance EVER.



Ashton Kutcher and Demi Moore: 16 year gap

Everyone was so shocked when Demi Moore and Ashton Kutcher hooked up that most assumed it was an elaborate stunt designed to “Punk” us all. Things didn’t work out between the pair. Kutcher is now married to Mila Kunis.



Mariah Carey and Nick Cannon: 10 year gap

Mariah Carey shocked everyone with her out-of-nowhere marriage to Nick Cannon. They have since split.



Geena Davis and Dr. Reeza Jarrahy: 15 year gap

Everyone was shocked by the union of Ashton and Demi. However, few seemed to notice that the age difference between Geena Davis and her fourth husband Dr. Reeza Jarrahy.



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