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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 31, 2012

Before Playboy mogul Hugh Hefner takes a trip to the altar to marry on-again, off-again girlfriend Crystal Harris, take a trip down memory lane with omg! as we look back at some of Hef's gal pals from over the years.