Julia Stiles

Character: Carolina

Alessandro Nivola

Character: Albert Morris

Shirley MacLaine

Character: Grandmother Mirabeau

Mika Boorem

Character: Maine Mirabeau

Azura Skye

Character: Georgia Mirabeau

Edward Atterton

Character: Heath Pierson

Randy Quaid

Character: Ted Mirabeau

Dwight Armstrong

Character: Snake

Ana Ortiz

Character: Christen

Jennifer Coolidge

Character: Aunt Marilyn

Barbara Eden

Character: Daphne St. Claire

Ambyr Childers

Character: Young Carolina

Lisa Sheridan

Character: Debbie

Daveigh Chase

Character: Young Georgia

Laura Ford

Character: Kate

Alan Thicke

Character: Chuck McBride - Perfect Date Host

John Capodice

Character: Ernie the Cook

Lauri Johnson

Character: Susan the Waitress

Kate Flannery

Character: Café Waitress

Michael Panes

Character: John

Ryan Scott Greene

Character: Seth

Curt Clendenin

Character: Perfect Date Audience Member (uncredited)