Hugh Hefner's Many Exes

Kimberly Conrad
After 30 years of living as a bachelor (and a busy one at that), Hef decided to make another trip down the aisle at age 63, this time to marry a 1988 Playmate of the Month, Kimberly Conrad, who was just 27 at the time. Conrad gave birth to Hef’s other two children, sons Maston and Cooper, now 22 and 21 respectively. Hef and his second wife split after nine years together, but Hef didn’t actually file for divorce until 2009, ... more 

Kimberly Conrad
After 30 years of living as a bachelor (and a busy one at that), Hef decided to make another trip down the aisle at age 63, this time to marry a 1988 Playmate of the Month, Kimberly Conrad, who was just 27 at the time. Conrad gave birth to Hef’s other two children, sons Maston and Cooper, now 22 and 21 respectively. Hef and his second wife split after nine years together, but Hef didn’t actually file for divorce until 2009, shortly after Cooper turned 18, when he asked a judge to reduce his spousal support from $40,000 to $20,000 a month. Throughout their separation, Conrad had lived with the couple’s sons in a house conveniently located next door to the Playboy mansion. less