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- The girls and Hef visit Chicago, Hef's hometown.
- Kendra and Bridget spend time with their families while Holly stays at the mansion with Hef. Bridget goes to Chicago to visit the Playboy offices & the city with her mother. Kendra & her family (mother, grandmother, grandfather & brother) work on Kendra's condo in San Diego, cleaning it up. Holly stays at the mansion working on Playmate photos with Hef.
- Holly's search for the 55th Anniversary Playmate starts with casting calls at the Mansion and in Chicago.