Julia Stiles as Carolina

Alessandro Nivola as Albert Morris

Shirley MacLaine as Grandmother Mirabeau

Mika Boorem as Maine Mirabeau

Azura Skye as Georgia Mirabeau

Edward Atterton as Heath Pierson

Randy Quaid as Ted Mirabeau

Dwight Armstrong as Snake

Ana Ortiz as Christen

Jennifer Coolidge as Aunt Marilyn

Barbara Eden as Daphne St. Claire

Ambyr Childers as Young Carolina

Lisa Sheridan as Debbie

Daveigh Chase as Young Georgia

Laura Ford as Kate

Alan Thicke as Chuck McBride - Perfect Date Host

John Capodice as Ernie the Cook

Lauri Johnson as Susan the Waitress

Kate Flannery as Café Waitress

Michael Panes as John

Ryan Scott Greene as Seth

Curt Clendenin as Perfect Date Audience Member (uncredited)