Maybelline Mary Katherine Mary Ann Chestnut, also known as "Maybe," lives an unconventional life. Her mother, Chessy, is a former beauty pageant queen who makes a living training teen beauty queens. Maybe is not one of those teen queens. In fact, Maybe makes a point of being exactly the opposite of the girls her mother coaches. Chessy is getting married for the seventh time and Maybe has had enough. Following an awful incident with Jake (husband-to-be #7), Maybe decides to leave for California with her friends Hollywood (who is going to start college) and Ted on an adventure to find her father.
Upon arriving in California, Hollywood and Ted quickly assimilate into their new lives. Maybe, however, struggles. She can't find a place to stay, her belongings are stolen, and she doesn't really know how to go about finding her father. Hollywood quickly tires of having Ted and Maybe live in his dorm room, so they must find other accommodations. While Ted has found a job working for an aging starlet, he also finds Sammy (husband #2 and #4) who moved to California to pursue his career as a photographer. Maybe moves in with Sammy and finds a job. While living with Sammy, Maybe is forced to confront some difficult truths about her mother and herself, which, in the end just may make her stronger and repair her relationship with Chessy.