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Hugh’s Highs And Lows: Inside Hefner’s Sexual Conquests, Girlfriends & Nasty Divorces

Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
Source: Getty Images

Sep. 29 2017, Published 7:59 p.m. ET

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
Source: Getty Images

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.

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
Source: Getty Images

“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.

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
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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.

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
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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.

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
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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.

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
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Kimberly Conrad

Before becoming Gene Simmons’ longtime love, Canadian actress Shannon Tweed briefly dated Hefner, and became Miss November 1981.

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
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Hefner married for a second time in 1989, saying “I do” to Miss January 1988, Kimberly Conrad.

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They were together for nine years and had two children - Marston and Cooper.

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
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Of course, one of Hefner's most publicized relationships was with The Girls Next Door in 2005.

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
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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.

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Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
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After that relationship fizzled, Hef downsized — and dated only two women: 20-year old twins Kristina and Karissa Shannon.

Hugh Hefner – Inside The Playboy Founder’s Sexual Conquests, Girlfriends, Wives And Nasty Divorces.
Source: Getty Images

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 tips@radaronline.com, or call us at 800-344-9598 any time, day or night.

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