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Holly Madison Cullen (born December 23, 1979) is an American model and television personality, best known for appearing as Hugh Hefner's number one girlfriend with Bridget Marquardt and Kendra Wilkinson on the reality television series The Girls Next Door. Although not a Playboy Playmate, she has appeared in nude pictorials with her Girls Next Door costars and fellow Hefner girlfriends Bridget ...Bunny Holly Madison offered a bleak picture of her time in her book Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny. “Everyone thinks that the infamous ...Holly Madison dated Hugh Hefner from 2001 to 2008. The Playboy founder died in 2017 ... "When you would go out with Hef, he's taking all kinds of naked pictures of these women when we're wasted ...The Kendra on Top alum, who moved into the mansion in 2004, noted that she hasn't spoken to the Holly's World alum, 41, in 10 years, adding, "I don't even know them. 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