Never Been Kissed

Never Been Kissed (1999) is a romantic comedy directed by Raja Gosnell — watch it online on iFILM. Drew Barrymore plays Josie Geller, a 25-year-old copy editor at the Chicago Sun-Times who has never quite figured out how people actually connect. When her editor sends her undercover at a high school to write a feature from the inside, Josie walks straight back into the worst years of her life.

She is awkward, over-eager, and completely out of her depth. Her brother Rob, played by David Arquette, tries to fast-track her into the popular crowd — with predictably chaotic results. Things get genuinely complicated when Josie develops real feelings for her English teacher Sam Coulson, played by Michael Vartan.

The film has a relaxed, mid-summer feel that holds up well, and sharp viewers will catch early appearances by Jessica Alba, John C. Reilly, and James Franco. A crowd-pleasing, low-pressure comedy with a warm payoff. Stream Never Been Kissed (1999) online on iFILM.