AceShowbiz - Hugh Hefner's reputation as a ladies' man didn't make it shocking at all that he was dating former Playboy Playmate Crystal Harris, though she was only 22 and he was 82 at the time. But it was his decision to marry her in his latter age that raised eyebrows. The model got cold feet five days before their supposed wedding in June 2011. They engaged in humiliating public spats for about a year, but later reconciled in 2012 and eventually got married on December 31 of the same year. Declaring his pure love for his third wife, the Playboy founder said before their wedding, "The dramatic age difference between difference & Crystal & me really doesn't matter. Whatever time I have left, we want to spend together." True to his words, they remained together until his death in September 2017.