Never Been Kissed is a 1999 comedy directed by Raja Gosnell and starring Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon, Leelee Sobieski, John C. Reilly, Jessica Alba, Marley Shelton, James Franco, Giuseppe Andrews, Jeremy Jordan and Garry Marshall.

Taglines:
The Class Clown Just Turned Chic.
A Comedy With Class.
She's never been hip. Never been cool. Never been in... Until now.
Some things are worth waiting for.

The main characters include:
Josie Geller - (Drew Barrymore) a young copy editor who works for the Chicago Sun-Times; and who is assigned to go undercover at a local high school for her first story. Unfortunately, Josie's high school years were marked with cruelty from other students and the scar of her nickname "Josie-Grossie".
Sam Coulson - (Michael Vartan) a young, attractive English teacher at the high school in which Josie enrolls.
Rob Geller - (David Arquette) Josie's younger brother; who, in contrast to Josie, was popular during his high school years and uses what he knows about popularity to help Josie in her assignment.

Barrymore plays 25-year-old Josie Geller, a one-time high school misfit turned pedantic and lonely copy-editor for the Chicago Sun-Times. Josie desperately wants to be a reporter, and constantly sends story ideas to her boss, Gus (John C. Reilly). One day during a staff meeting, the tyrannical editor-in-chief, Rigfort (Garry Marshall), assigns her to pose as a high school student for her first story, an undercover feature. The aim of the story is to gain the trust of the pretty, popular girls (including Kirsten, played by Jessica Alba), who are stereotypically vain and intolerant of anyone who is not like them; and the highschool heart-throb, Guy Perkins (Jeremy Jordan). At first, despite her best efforts and the support of her best friend at the paper, Anita (Molly Shannon), Josie reverts back to her geeky, misfit, high school persona, and becomes friends with fellow geek Aldys (Leelee Sobieski). However, after counselling by her brother, Rob (and with the benefit of hindsight of her original high school career), Josie learns how to not only fit in, but thrive. A subplot involving the attraction between Josie (who has never had a romance) and young English teacher Sam Coulson is complicated by the fact that Sam thinks Josie is 17 years old and a student, and therefore out of bounds.