Is holly still dating hugh hefner

More acting gigs followed until Brande took on her most challenging role: proving her business savvy on Donald Trump's "Celebrity Apprentice." The brainy beauty came in third but was still the target of Joan and Melissa Rivers' dumb blonde rants.

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Bridget Marquardt had a couple of failed test shoots for a Playmate slot and was rejected from the mag but welcomed into Hef's house.Carrie eventually dropped the litigation, but we wonder if she was still trying to get at Hefner when she launched "Playboy" competitor "Nude" magazine in 2008.Kimberly Conrad 1989 was a good year for Kimberly Conrad: the former Miss January 1988 was named Playmate of the Year AND she ended Hugh Hefner's 35-year bachelor spree by marrying the ultimate playboy.Photo gallery: See Hef's girlfriends through the years.Barbi Benton Back in 1968 it was only kind of creepy that 42-year-old Hugh Hefner was dating an 18-year-old.

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