Never Been Kissed is a romantic comedy that follows Josie Geller (Drew Barrymore), a 25-year-old copy editor at the Chicago Sun-Times, who longs to be a reporter. Given her first assignment, Josie must go undercover as a high school student to investigate the lives of teenagers for a feature story.

Returning to high school is a daunting task for Josie, who was socially awkward and unpopular during her teenage years. Determined to succeed, she adopts a new persona and tries to fit in with the popular crowd. Along the way, Josie befriends Aldys (Leelee Sobieski), a fellow outsider, and struggles to balance her professional duties with the emotional challenges of reliving her adolescence.

As Josie navigates the complexities of high school life, she develops a crush on her charming English teacher, Sam Coulson (Michael Vartan), complicating her assignment. The film culminates in a prom night revelation, where Josie must decide between her career ambitions and following her heart, leading to a heartwarming and humorous conclusion about love and self-discovery.