Content Warning: This section discusses women’s objectification, sex work, sexual intercourse, substance abuse, and suicidal ideation.

Holly is the author of and main protagonist in Down the Rabbit Hole. As a little girl growing up in Alaska, she becomes enthralled with Marilyn Monroe and fantasizes about living a life of public adulation and fame. Her dreams compel her to obtain plastic surgery and later move to Los Angeles for an acting career. She initially intends to finish college, but financial pressures compel her to abandon this plan. She supports herself by modeling and waitressing at Hooters.

At 20, she receives an unexpected invitation to a Playboy Mansion pool party, where she meets Hefner for the first time. She agrees to become one of Hefner’s girlfriends after realizing that she will be unable to pay her rent once her roommates leave. She quickly becomes Hefner’s main girlfriend.

Though Holly eventually learns that Hefner thought she was quite attractive from the moment she arrived at the mansion, her self-doubt and insecurities intensify during her years with him. Depressed, confused, suicidal, and in need of help, the author finds herself struggling to understand why her glamorous life is so unfulfilling. She feels besieged by the jealousy of Hefner’s other girlfriends, as well as Hefner’s personal cruelty.