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

Ana Ortiz

Christen

Jennifer Coolidge

Aunt Marilyn

Barbara Eden

Daphne St. Claire

Ambyr Childers

Young Carolina

Lisa Sheridan

Debbie

Daveigh Chase

Young Georgia

Alan Thicke

Chuck McBride - Perfect Date Host

John Capodice

Ernie the Cook

Lauri Johnson

Susan the Waitress

Kate Flannery

Café Waitress

Michael Panes

John

Curt Clendenin

Perfect Date Audience Member (uncredited)