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Forever a ladies' man, Hugh Hefner has had many girlfriends throughout the years!The almost 91-year-old founder and chief creative officer of Playboy Enterprises has infamously dated blonde after blonde, most notoriously courting the cast members of the short-lived reality series .Even though he's certainly had his fill of bombshells — previously admitting to sleeping with "more than" 1,000 women — Hef maintains that he always stayed faithful during the multiple times he was married.

Hefner is a native of Chicago, Illinois, and a former journalist for Esquire.

(Photo Credit: Getty Images) Hef, a distinguished polygamist with a reported net worth of million, has famously welcomed his multiple girlfriends to live in his house, also known as the Playboy Mansion. 1 girlfriend" of seven years, Holly Madison — who has since outed many of the Mansion's secrets (like what sex with Hef was like and how she was offered prescription drugs!

) — Hugh tied the knot with Crystal Harris in 2012. MORE: Kendra Wilkinson Believed False Reports Claiming Hugh Hefner Was Dead — Plus Their Throwback Pics!

The first issue, published in December 1953, featured Marilyn Monroe from her 1949 nude calendar shoot and sold over 50,000 copies.) After the Charles Beaumont science fiction short story "The Crooked Man" was rejected by Esquire magazine in 1955, Hefner agreed to publish it in Playboy.

The story highlighted straight men being persecuted in a world where homosexuality was the norm.




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