These rolls in work eventually led to invitations to the Playboy Mansion, at a time when Hefner had seven girlfriends. Holly moved into the mansion and became one of Hefner's official girlfriends in August 2001, after more than a year of visiting the mansion. In February 2002, after all but two of his girlfriends left, Madison became Heft's "number 1 Girl" and moved into his bedroom at the mansion. Hefner's two other girlfriends, Bridget Marquardt and Kendra Wilkinson, have their own bedrooms off the story.
In season Three of the show during the episode My Bare Lady, Holly stated that she wants to have a career producing Playboy spreads and working for Hugh Heffner. Holly also helped design and put together the new Girls Next Door calendar for Hugh.
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