Hugh Hefner was never a lonely man. The bathrobe-clad lothario famously bragged of bedding over a thousand women. But the ultimate Playboy, who died Wednesday at the age of 91, admitted late in his life that he never really found his soulmate. Click through RadarOnline.com's gallery to discover some of his greatest conquests…and heartbreaks.
“There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn't married,” Hef once bragged to Esquire. “You have to keep your hand in.”
For all his promiscuity, Hefner was only married three times. His first was to college sweetheart Mildred Williams in 1949. The couple had two children together, Christie and David Hefner.
But Hef was reportedly heartbroken when he learned that Mildred cheated on him while he was in the military, and the two divorced a decade later.
Hefner would then go on a tear, dating a bevy of Playboy models and bunnies. In 1968, when he was 42-years-old, Hef convinced his 18-year-old trophy, Barbara Klein, to change her name. And she did.
The now Barbi Benton went on to star in several B-movies and tv shows. Of course, she also posed for Playboy. And she even helped Hef discover his ultimate home, the Playboy Mansion. They dated until 1976.
Before becoming Gene Simmons’ longtime love, Canadian actress Shannon Tweed briefly dated Hefner, and became Miss November 1981.
Hefner married for a second time in 1989, saying “I do” to Miss January 1988, Kimberly Conrad.
They were together for nine years and had two children - Marston and Cooper.
Of course, one of Hefner's most publicized relationships was with The Girls Next Door in 2005.
Hef let cameras roll as he dated three different women, Holly Madison, Bridget Marquardt, and Kendra Wilkinson, at the same time. The reality show lasted six seasons.
After that relationship fizzled, Hef downsized — and dated only two women: 20-year old twins Kristina and Karissa Shannon.
Finally, on New Year’s Eve 2012, Hefner, by then 86, wed 30-year-old model Crystal Harris. They were together until the day he died. We pay for juicy info! Do you have a story for RadarOnline.com? Email us at firstname.lastname@example.org, or call us at 800-344-9598 any time, day or night.