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Sandy and Mandy Bentley

E367623 01: (ITALY OUT) Hugh Hefner, center, celebrates the upcoming May issue of Playboy with his girlfriends, cover girls Sandy and Mandy Bentley, April 12, 2000 in New York City. (Photo by Arnaldo Magnani)

Hugh Hefner's Many Exes

December 28, 2012

Playboy mogul Hugh Hefner finally tied the knot with on-again, off-again girlfriend Crystal Harris on December 31, 2012. But she wasn't the first girl to win his heart. Take a

trip down memory lane with omg! as we look back at some of Hef's

gal pals from over the years.