The story follows Josie Geller (Drew Barrymore), a socially awkward copy editor for the Chicago Sun-Times who dreams of becoming a reporter. When her editor, Rigfort (Garry Marshall), assigns her to go undercover as a high school student to uncover teenage culture, Josie sees it as an opportunity to relive her high school years and finally fit in.
As Josie navigates the challenges of high school, she struggles to shake off her nerdy persona and make friends. However, she finds herself drawn to her English teacher, Sam Coulson (Michael Vartan), and forms a close bond with her popular younger brother, Rob (David Arquette), who is posing as a student to support Josie’s mission.
Despite her initial awkwardness, Josie begins to find her place in the high school social scene and gains popularity among her peers. She also starts to develop genuine feelings for Sam, who reciprocates her affections but is hesitant to act on them due to the professional boundaries between them.
As Josie’s investigation progresses, she faces moral dilemmas and struggles with her identity as she grapples with the consequences of her deception. Her relationship with Sam becomes increasingly complicated, and she must decide whether to reveal the truth about her assignment and risk losing everything she has gained.
In a climactic moment, Josie decides to come clean about her true identity during a school-wide prom night. She confesses her feelings for Sam and apologizes for deceiving everyone. Despite initial shock and betrayal from her peers, Josie’s honesty and vulnerability win them over, and they forgive her.
In the end, Josie’s article is published, and she achieves her dream of becoming a successful reporter. She also reconciles with Sam, who realizes that their connection transcends the boundaries of their professional roles. The film concludes with Josie and Sam sharing a romantic kiss, finally finding happiness together.
“Never Been Kissed” is a heartwarming and comedic tale of self-discovery, redemption, and the transformative power of love. With its relatable characters, humorous moments, and heartfelt themes, it remains a beloved classic in the romantic comedy genre.