The Many Loves Of Hugh Hefner, The Luckiest Bastard In The World

Kimberly Conrad
Playmate of the Year 1989 Kimberly Conrad was Hef's second fling with marriage, a relationship that resulted in Hef's two sons Marston and Cooper. The couple split up less than a decade later, prompting Hugh to note that, "I was married and faithful for eight years in the 1980s, and following that, as an overreaction to that failed marriage, I wound up with seven live-in girlfriends. Dealing with those seven girlfriends was easier than dealing with one wife." Now that's a burn right there! The couple was actually married for nine years, and remained separated for 11 years before they eventually divorced, which meant they were technically together until SEPTEMBER 2009! Since Hef was 98 at the time, it's understandable that he might have forgotten to file the papers, but still. Yeesh. [Photo: Getty Images]