Never Been Kissed

Josie Geller, a shy, baby-faced junior copy editor at the Chicago Sun-Times, is tasked with studying teenage life by going undercover at her former high school. With help from her practical brother Rob, she infiltrates the campus's most popular crowd and observes how popularity, slang, and trends shape daily life. What starts as a straightforward assignment gradually pulls her into a world that feels both alien and familiar. She moves through classrooms, halls, and cafeteria chatter. As Josie navigates the social maze, she also grapples with her own yearning for connection and a surprising romantic spark with her English teacher, Sam Coulson, complicating her mission and forcing her to decide what parts of herself she wants to reveal in secret.

Released in 1999, Never Been Kissed was directed by Raja Gosnell and based on a screenplay by Abby Kohn and Marc Silverstein. Film paired Drew Barrymore with David Arquette and Michael Vartan, supported by Jessica Alba in a key role.

With a budget of 25 million, it grossed about 84.6 million worldwide, including solid domestic numbers and steady international receipts, signaling a strong return for a romantic comedy of its era and contributing to Barrymore's rising star status and beyond.

The film helped cement a late 90s rom com formula in which an outsider infiltrates high school life and discovers her voice. Barrymore's quick humor and the undercover premise left a recognizable mark on pop culture, with fashion moments and disguises echoing in later comedies in film history for fans.

Critics generally praised Barrymore's warmth and the film's cheerful energy, while some noted it relies on familiar rom com beats. The story explores identity and the balance between professional ambition and personal longing, showing how honesty and self-acceptance can reshape both love and life. The tone remains buoyant and affectionate.