Kate Spencer is a teenage girl who lives with her single mother, Lori, whose poor taste in men causes them to move around frequently. Kate and her mother move to a suburb of Portland, Oregon, where Kate gets a job as a waitress. While at work, she sees popular local boy John Tucker on dates with three different girls: chronic overachiever Carrie, head cheerleader Heather, and promiscuous and liberal vegan activist Beth. Kate learns from a co-worker that John dates girls from different cliques at his school so that they never interact. John convinces the girls to keep their relationships secret by claiming his father forbids him to date during basketball season.