21 Celeb Couples With Bizarre Age Gaps

4. Hugh Hefner and Crystal Harris

The 88-year-old playboy Hugh Hefner is the first magazine publisher to become a huge celebrity. He lives in the famous Playboy Mansion in Los Angeles where many lavish parties took place during the past few decades.

The Playboy founder said that he had slept with over a thousand women during his lifetime.

“How could I possibly know? Over a thousand, I’m sure. There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn’t married. You have to keep your hand in.”

Hefner was married to Mildred Williams in 1949 and they have two children. His second wife was Playmate of the Year Kimberley Conrad whom he divorced in 2010. The couple was separated since 1998 and Hugh had numerous relationships with young models that appeared in his magazine.

In 2008 Hefner started dating three girls, one of which was Crystal Harris. He finally proposed to Harris in 2010.

“All our friends think it’s made in heaven,” Hefner told in an interview to Esquire. “It’s only people who don’t know us, who simply see us as stereotypes in terms of age and beauty… I just feel very, very fortunate to have found her at this stage in my life. I saved the best till last.”

Hefner and Harris planned to get married on June 18, 2011 but Hugh called the wedding off five days prior to the ceremony. However, the couple got back together and were married on December 21, 2012. Hefner was 86 and the beautiful Harris only 26!

In a recent interview, Harris confessed that she married Hefner because of security.

Christopher Polk / Getty Images Entertainment / Getty Images

‘Well for me it meant more security, knowing that I am the one for him.’’
‘’Like we were talking about, there are always girls in and out and always the feeling of maybe being replaced… And he made sure I didn’t feel that way anymore and that was what the wedding was all about.‘’

Harris also once revealed that their sex lasted for ‘like two seconds.’