Julia Stiles
Carolina
Alessandro Nivola
Albert Morris
Shirley MacLaine
Grandmother Mirabeau
Mika Boorem
Maine Mirabeau
Azura Skye
Georgia Mirabeau
Edward Atterton
Heath Pierson
Randy Quaid
Ted Mirabeau
Dwight Armstrong
Snake
Ana Ortiz
Christen
Jennifer Coolidge
Aunt Marilyn
Barbara Eden
Daphne St. Claire
Ambyr Childers
Young Carolina
Lisa Sheridan
Debbie
Daveigh Chase
Young Georgia
Laura Ford
Kate
Alan Thicke
Chuck McBride - Perfect Date Host
John Capodice
Ernie the Cook
Lauri Johnson
Susan the Waitress
Kate Flannery
Café Waitress
Michael Panes
John
Ryan Scott Greene
Seth
Curt Clendenin
Perfect Date Audience Member (uncredited)