Pilby (Powley) is a genius who graduated Harvard at 18. Convinced that the world is populated by oversexed hypocrites, she has a hard time making sense of life as it relates to morality, relationships, sex and leaving her apartment. In an effort to coax Carrie out of her shell, her psychiatrist (Nathan Lane), makes a deceptively simple checklist of goals for her to achieve between Thanksgiving and the year's end. Each goal brings Carrie closer to the understanding that humans, like books, can't be judged by their covers.