Story :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.
Cast
Jason SchwartzmanMax Fischer
Bill MurrayHerman Blume
Olivia WilliamsRosemary Cross
Seymour CasselBert Fischer
Brian CoxDr. Nelson Guggenheim
Mason GambleDirk Calloway
Sara TanakaMargaret Yang
Stephen McColeMagnus Buchan
Luke WilsonDr. Peter Flynn
Dipak PallanaMr. Adams
Andrew WilsonCoach Beck
Marietta MarichMrs. Guggenheim
Ronnie McCawleyRonny Blume
Keith McCawleyDonny Blume
Hae Joon LeeAlex
Adebayo AsabiMr. Obiamiwe
Connie NielsenMrs. Calloway
Al FielderErnie
Colin PlattBoy Portraying Frank Serpico
George FarishO'Reilly
Francis FernandezBurnum
McCauley PenderdastFields
Eric WeemsWillie
Dalton TomlinWrestler
Wallace WolodarskyReferee
Kim TerryMrs. Blume
Ella PryorWoman Back Stage
Paul SchiffWaiter
Antoni ScaranoSmall Boy Artist
Brian TenenbaumContractor
Thayer McClanahanSchool Reporter
Patricia WinklerMrs. Whitney
Manning MottMr. Holstead
J.J. StonebrakerWoody
Donny Caicedo40 Ounce
Ali KtiriBenjamin
Michael MaggartConcierge
Robbie LeeIsaac
Morgan RedmondBellman
Ed GeldartSecurity Guard
J.J. KillaleaTommy Stalling
William LauMr. Yang
Lucille SadikinMrs. Yang
Steve EckelmanTennis Pro
Eric Chase AndersonArchitect
Danny FineCoach Fritz
Kyle Ryan UrquhartRegis
Kumar PallanaMr. LittleJeans
Stephen DignanReuben
Alexis BledelStudent (uncredited)
Brandon TrostVietnamese Soldier with Rocket Launcher (uncredited)