Kris Isacsson Director, Writer Freddie Prinze Jr. Alfred "Al" Connelly Actor Julia Stiles Imogen Actor Selma Blair Cyrus Actor Shawn Hatosy Eddie Hicks Actor Zak Orth Monk Jablonski Actor Ashton Kutcher Jim Morrison Actor Rosario Dawson Lana Actor Henry Winkler Chef Ray Connelly Actor Lucie Arnaz Judy Connelly Actor Lauren German Lovestruck Woman Actor Zay Harding Young Man Actor Amanda Barfield Faith Keenan Actor Chloe Hunter Megan Brodski Actor Granger Green Haley Heller Actor Jed Rhein Gabe Stiano, New Age Actor Joseff Stevenson Ted McGurran, Allergic Actor Elizabeth Levin Carbs Girl Actor Lola Glaudini Parolee Actor Robin Nance Daddy's Girl Actor Mary Wigmore Pearly Whites Actor Julian Michael Caiazzo Al at 5 Years Actor Bobby Cohen Executive Producer Hugo Heppell Associate Producer Trish Hofmann Co-Producer Jason Kliot Producer Jeremy Kramer Executive Producer Joana Vincente Producer Bob Weinstein Executive Producer Harvey Weinstein Executive Producer Edmund Choi Original Music Robert Yeoman Cinematographer Stephen A. Rotter Film Editing Douglas Aibel Casting Kevin Thompson Production Design Marc Dabe Art Director Tracey Gallacher Art Director Ford Wheeler Set Decoration Michael Clancy Costume Design