James Franco (who portrays Chris) and Marla Sokoloff (who portrays Maggie) started dating while filming this movie. Their relationship lasted 5 years (1999-2004).
This movie was filmed at Torrance High School in Torrance, California. She's All That (1999) was also filmed at this school. Jodi Lyn O'Keefe co-starred in both movies.
Shane West portrays Ryan in this film, a nerd who falls for a girl. In A Walk to Remember (2002), he portrays the very non-nerdy cool guy, named Landon Carter, who also falls for a girl.