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Cast Anastasia Case ..... Bridget's Sister Audra Lynn ..... Herself Bridget Marquardt ..... Herself David Phillips ..... Michael-David Winery Owner Holly Madison ..... Herself Hugh M. Hefner ..... Himself Jeff Case ..... Bridget's Stepfather Jillian Grace ..... Herself Judy Case ..... Bridget's Mom Kara Monaco ..... Herself Kendra Wilkinson ..... Herself Sara Jean Underwood ..... Herself Stacy Berk ..... Hef's Ex-Girlfriend

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