Couples 49 Famous Couples with Huge Age Differences  

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List of famous couples with the greatest age differences. Enjoy these pictures of celebrities whose significant others are young enough to be their kids or old enough to be their grandfathers. That's right, we're looking at you, Hugh Hefner and Woody Allen. But hey, as Hef's ex-girlfriend Kendra Wilkinson said, when asked how on earth she was dating an ancient human being, "age ain't nothin' but a number." So check out this list of celeb couples with epic age gaps.

Married couple Harrison Ford and Calista Flockhart have a child, but with a 22 age year difference, Ford could have been Flockhart's own dad. Kind of weird to think about, huh? Of course, Demi Moore ditched Bruce Willis for a man 16 years her younger. Ashton Kutcher was her boy toy before he moved on to a similarly-aged Mila Kunis, but he would have been a newborn at Moore's Sweet Sixteen party.

Dating or marrying someone decades older or younger isn't exclusive to Hollywood, but, as evidenced by this list, it's pretty damn prevalent.


Dick Van Dyke is listed (or ranked) 1 on the list 49 Famous Couples with Huge Age Differences
Photo: via Imgur
Relationship: Started dating 2006, married in 2012
Dick Van Dyke: b. 1925 with 4 children born between 1948-58
Arlene Silver: b. 1971
Age Difference: 46 years see more on Dick Van Dyke

Hugh Hefner is listed (or ranked) 2 on the list 49 Famous Couples with Huge Age Differences
Photo: via Twitter

Relationship: Started dating in 2008, engaged in 2011, married in 2012, divorced in 2017
Hugh Hefner: b. 1926 with 4 children born 1952, 1955, 1990, and 1991
Crystal Harris: b. 1986
Age Difference: 60 years

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Patrick Stewart is listed (or ranked) 3 on the list 49 Famous Couples with Huge Age Differences
Photo: via Twitter

Relationship: Started dating in 2009, engaged in 2013, married in 2013
Patrick Stewart: b. 1940 with 2 children born 1967 and 1973
Sunny Ozell: b. 1978
Age Difference: 38 years

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Charlie Chaplin is listed (or ranked) 4 on the list 49 Famous Couples with Huge Age Differences
Photo: via Twitter
Relationship: Married in 1943, had 8 children between 1944 and 1962
Charlie Chaplin: b. 1889 with 3 children born 1919, 1925, and 1926
Oona O'Neill: b. 1925
Age Difference: 36 years see more on Charlie Chaplin