Famous May-December Couples: Some Work, Some Don’t

Love is love and sometimes love spans several years and even decades. No, it’s not the plot to a bad Keanu Reeves movie. May-December couples are certainly nothing new among celebrities, but they do attract attention. Unfortunately, such relationships don’t always last. Just ask Hugh Hefner. The Playboy founder has had a string of younger beauties, including his recent almost-bride Crystal Harris, 60 years his senior.

Not all younger-older match-ups are doomed. Demi Moore and new “Two and a Half Men” star Ashton Kutcher have been happily married for six years despite a 16 year age difference. Tom Cruise and Katie Holmes have the same age difference and their relationship appears solid. The union even resulted in a daughter, Suri. Kelsey Grammar, 55, appears very happy with his new 29-year-old girlfriend Kayte Walsh.

There does appear to be a double-standard though with nobody batting an eye at younger partners for Clint Eastwood (Dina Ruiz, 46), Michael Douglas (Catherine Zeta-Jones, 41) and Harrison Ford (Calista Flockhart, 46). Yet, when Jennifer Aniston and Cameron Diaz are spotted with younger guys they are labeled cougars. The next time you see your favorite star, you might just be wondering if the partner at their side is a spouse or one of their children.