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, Bowfinger, Shopgirl Also Ranked #20 on The Most Trustworthy Celebrities in the World #7 on The Funniest People of All Time #97 on Celebrities Who Should Run for President #8 on The Funniest Stand Up Comedians of All Time Clint Eastwood married Dina Ruiz on March 31, 1996, when he was 66 years old and she was 31. Despite an age gap of more than a decade, Colleen Smith and her husband Damian cite many factors that make their marriage work, including her role as the oldest child in her family and their common interests.Hugh Hefner married Crystal Harris on December 31, 2012 when he was 86 and she was 26. Other famous men who have married much younger women include Frank Sinatra, Kevin Costner and Woody Allen.Why do you think so many men choose to marry women who are half their age? Larry King married Shawn Southwick in 1997 when he was 64 and she was 38. King has been married seven times previously to six different women.Prior to dating Sklar, Seinfeld was in a relationship with 17 year-old high school student Shoshanna Lonstein. Age: 62 Birthplace: New York City, New York, United States of America Profession: Television producer, Film Producer, Screenwriter, Actor, Voice acting, more Credits: Seinfeld, Jerry Seinfeld: 'I'm Telling You for the Last Time', Comedian, Bee Movie Also Ranked #18 on The Funniest People of All Time #9 on The Funniest Stand Up Comedians of All Time #32 on The Best TV Actors of All Time #6 on Celebrities Whose Lives You Want Steve Martin married Anne Stringfield on July 28, 2007 when he was 62 and she was 36.The couple are still married today, and their first child was born in 2012.

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Many of Hollywood's leading men have married much younger women.

This is Melania's first and only marriage and Trump has been married twice before.

Another famous entrepreneur Rupert Murdoch married Wendy Deng in 1999 when he was 68 and she was 30. Hefner has been married twice previously and he has been in several long-term relationships.

We have been divorced for 2 years and although it saddens me that my family has been broken apart, I am happy that my ex and I have have managed to be civil enough to make it okay for the kids.

Here is what I have found: For single men the options are plentiful. It seems that the breakdown of available women fall into the following categories: 1.

Be cautious men, these women are looking for you to do it all over again and that means house and children.

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