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Hugh Hefner Reveals The Insane Number Of Women He's Slept With

Aly Weisman   

Hugh Hefner Reveals The Insane Number Of Women He's Slept With

Hugh Hefner Playboy Playmates

Alberto E. Rodriguez/Getty

Hugh Hefner has dated up to seven women at one time, as shown on his popular E! reality show "Girls Next Door."

Hugh Hefner, 86, is currently on his third wife, but that's nothing compared to the amount of women the Playboy founder has slept with throughout his lifetime.

“Over a thousand, I’m sure," Hefner revealed to Esquire of the number of women he's had sexual relations with. But it's not an exact number, as he says, "How could I possibly know?"

But Hefner's sexual escapades have nothing to do with him being unfaithful to his wives.

“There were chunks of my life when I was married, and when I was married I never cheated,” explains the publishing icon. “But I made up for it when I wasn’t married. You have to keep your hand in.”

Hefner was first married in 1949 to Northwestern University student Mildred Williams, with whom he has two children, before divorcing in 1959.

40 years later, Hefner said "I do" again to Playmate of the Year Kimberley Conrad, whom he separated from in 1998 and finally divorced in 2010.

During the separation, Hefner dated up to seven women at once (with the help of Viagra) and featured his relationship with Playboy Playmates Holly Madison, Bridget Marquardt and Kendra Wilkinson on the popular E! reality series "The Girls Next Door."

hugh hefner playboy

Instagram @mermaidcrystal

Hugh Hefner, 86, married Crystal Harris, 26, last New Year's Eve.

On New Year's Eve, Hefner married Crystal Harris, 60 years his junior, a year after the couple reconciled after she called off the wedding days before the initial ceremony was set to take place.

“He believes in love,” 26-year-old Harris told Esquire. “Hef loves me more than anybody else in a relationship ever has. It took me time away to realize that. I think I realized that here is where I’m meant to be.”

Adds Hefner, "All our friends think it’s made in heaven. It’s only people who don’t know us, who simply see us as stereotypes in terms of age and beauty… I just feel very, very fortunate to have found her at this stage in my life. I saved the best till last.”

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