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After years of living in the Playboy Mansion, Kendra Wilkinson decides to try to live outside of the sheltered lifestyle that the Playboy Mansion provides. Completely on her own for the first time in a long time, Kendra is beginning to experience things that she has been sheltered from. Getting a job, finding a place to live, and managing her own personal life turns out to be a little bit more that she bargained for.