Playboy founder Hugh Hefner is set to marry fiancée Crystal Harris at the Playboy Mansion on New Year's Eve, despite Harris famously calling off their wedding in 2011, just days before they were due to wed. Jewel-loving Crystal has even scored herself a brand new engagement ring, having reportedly sold off her old one.

Flamboyant 86-year-old millionaire extraordinaire Hugh Hefner has had no shortage of women knocking on his door, regardless of his advanced years. Obviously, some might harbour intentions far less noble than seeking romantic love. Which begs the question: Can someone so rich, famous and constantly surrounded by some of the world's most beautiful women ever hold down a proper relationship? We're not so sure. In any case, here's a look at some of some of Hefner's more prominent relationships.

Click through to see the women in Hugh Hefner's life.
December 28, 2012
Women feel more comfortable undressing in front of men than they do in front of other women. Women are too judgmental, and men are just grateful.