When a beautiful first-grade teacher arrives at a prep school, she soon attracts the attention of an ambitious teenager named Max, who quickly falls in love with her. Max turns to the father of two of his schoolmates for advice on how to woo the teacher. However, the situation soon gets complicated when Max's new friend becomes involved with her, setting the two pals against one another in a war for her attention.
Jason Schwartzman
as Max Fischer
Bill Murray
as Herman Blume
Olivia Williams
as Rosemary Cross
Seymour Cassel
as Bert Fischer
Brian Cox
as Dr. Nelson Guggenheim
Mason Gamble
as Dirk Calloway
Sara Tanaka
as Margaret Yang
Stephen McCole
as Magnus Buchan
Luke Wilson
as Dr. Peter Flynn
Dipak Pallana
as Mr. Adams
Andrew Wilson
as Coach Beck
Marietta Marich
as Mrs. Guggenheim
