- Holly's search for the 55th Anniversary Playmate starts with casting calls at the Mansion and in Chicago.
- Holly is in charge of finding the 55th Anniversary Playmate. She takes the responsibility seriously, especially after Hef tells her that he is looking for a "Playmate of the Year, times 55." The process starts with a mass casting call at the Mansion with hundreds of candidates having their pictures taken. Holly, Bridget, and a few of their Playmate friends then travel to Chicago for the casting call there. First they visit Playboy's headquarters and then go to the hotel where the casting call is being held. They see various women posing and being interviewed, but Holly is hoping to find a really special candidate to take back to Los Angeles. Holly and friends go to Hooters for lunch in hopes of finding potential Playmates there. They meet Crystal, a customer, who turns out to have auditioned for the Playmate search the day before. After spending more time at the casting call, Holly prepares to continue the Playmate search in Dallas and New York. Meanwhile, Kendra goes shopping for clothes and is surprised to find herself surrounded by paparazzi and fans. Later, she invites Hef to join her in a live Internet chat.—Anonymous
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