When Josie Geller (Drew Barrymore), a bright but socially-awkward magazine editor, gets an undercover assignment to pose as a high school student, she leaps at the chance to prove herself as a reporter. However, Josie quickly learns that life in high school isn’t any easier the second time around and she becomes a target for the cool-but-cruel popular kids. As the pressure to write the story grows, so does Josie’s attraction to her handsome and kind-hearted English teacher, Sam Coulson (Michael Vartan). Things start looking up when Josie’s brother, Rob (David Arquette), helps her win the cool kids over. But will her quest for the story jeopardize her chance at true love?

1999 — written by Abby Kohn and Marc Silverstein. Directed by Raja Gosnell.

Sources include:

Google Movie Synopsis

https://www.imdb.com/title/tt0151738/

https://en.wikipedia.org/wiki/Never_Been_Kissed