In one year, Holly goes from being Hefner’s newest, most junior girlfriend to the one with the most authority and seniority. He replaces all six Mean Girls with new women. Among them is Bridget, who becomes Holly’s fast friend. The new girlfriends have the same obligations and privileges as Hefner's previous entourage. Holly notices, however, that the luster around Hefner’s romantic companionship is not as great as it once was.

Holly and Bridget spend their idle time familiarizing themselves with the mansion’s grounds, and become official tour guides.

Holly, tired of Hefner’s clutter, gains permission to organize his bedroom. It is overflowing with useless objects, some of which are downright creepy. For instance, Hefner made The Guinness Book of World Records for owning more scrapbooks than anyone else in the world. His 2,000 scrapbooks contain photographs of all the women who attended events at the mansion, as well as memorabilia related to every woman he dated. For Holly, these scrapbooks are one manifestation of Hefner’s fixation on celebrity—both his own and that of the people around him.

Playboy Enterprises experiences further financial strain during Holly’s second year as Hefner’s girlfriend. In the hopes of reviving the business, he invites networks to film television specials at the Playboy Mansion.