Carolina

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)