Never Been Kissed (1999)

Drawing a blank? Well she DREW BARELY MORE than one when trying to remember her last true kiss.  Never Been Kissed starring Drew Barrymore, David Arquette and that sexy dude from Alias.

Drew Barrymore is an uptight copy editor with a checkered high school past who yearns to be a reporter.  One day she gets an opportunity to go undercover as a highschool student to write her first article abouthow kids these days REALLY live.  Determined to rewrite her past, Drew never expected she'd be copyediting her future, a future with a dashing, yet soulful kindred spirit, who happens to be HER ENGLISH TEACHER!  Don't stand so close to this one, fatties, cuz she's never been kissed and his kiss is on her LIST!Dave yearns for those glory days when he was a jock who could bully nerds on their own level: through chess.  Noah perfects his sunny surfer girl drawl. Almost.