29 Sep Hugh Hefner’s 31-Year-Old Widow Has Not Won The Gold Digger Lottery

When Hugh Hefner’s first marriage to his childhood sweetheart Mildred Williams ended in divorce in 1959, he began to live the Playboy lifestyle that we have all come to associate with the world’s most famous bachelor.

Against the odds he decided to tie the knot again in 1989, marrying Playmate of the Year Kimberly Conrad, only to separate in 1998 after having two children together. Following their divorce, Hefner said that he preferred to be single.

Then in his seventies, he continued to date women a fraction of his age including Holly Madison, Kendra Wilkinson and Bridget Marquardt, pictured below, whose relationships with him were famously depicted on The Girls Next Door.

Although Hefner had three live in girlfriends, Madison was his “number one girlfriend”, and the two shared a more serious relationship. Despite their 53-year age gap, she wanted to marry the Playboy mogul and have his children.

However, Hefner was unwilling to marry again, and when doctors confirmed that his sperm was no longer viable, Madison left him after seven years together. This came shortly after Wilkinson and Marquardt also decided to end their relationships with the man who made them household names.

The trio were almost immediately replaced by then 19-year-old twin playmates Kristina and Karissa Shannon and 23-year-old Crystal Harris, with Harris taking Madison’s place as Hefner’s number one girlfriend.

Harris went on to become a Playmate, posing for the December 2009 issue of Playboy.

Just two years into his relationship with Crystal, Hefner did the unthinkable and proposed. This came as a surprise to Crystal who claimed that she was not looking to marry the Playboy founder, but she accepted the proposal anyway.

But Hefner’s wife-to-be got cold feet five days before their wedding in 2011 and left Hefner during one of his movie nights. She then gave a shocking interview to Howard Stern, claiming that the two only ever slept together once.

“I have never seen him naked… I am not turned on by Hef. Sorry,” she revealed to Stern.

Harris publicly apologised for her comments and ended up marrying Hefner in December 2012, despite friends warning the Playboy founder not to. But, Hefner, clearly a clever man, made sure that he wasn’t going to be taken for a ride…

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