Jennifer Aniston as Nicole Hurley

Gerard Butler as Milo Boyd

Jason Sudeikis as Stewart

Jeff Garlin as Sid

Ritchie Coster as Ray

Cathy Moriarty as Irene

Peter Greene as Earl Mahler

Joel Marsh Garland as Dwight

Dorian Missick as Bobby Jenkins

Siobhan Fallon Hogan as Teresa

Carol Kane as Dawn

Adam Rose as Jimmy

Christine Baranski as Kitty Hurley

Gio Perez as Uncle Sam

Jason Kolotouros as Gelman

Matt Malloy as Gary

David Costabile as Arthur

Lynda Gravatt as Judge

Charlie Hewson as Rich Guy

Charles Techman as Track Vet

Lou Sumrall as Bone

Jayne Houdyshell as Landlady

Mary Testa as Maid at the Taj

Harry Zittel as Pedicab Driver

Tracy Thorne as Membership Director

Christian Borle as Caddy

Amanda Hope Dutton as Darla

Adam LeFevre as Edmund

Edward Mitchell as Jonathan

Patrick Mitchell as Jeremy

Brooke Allison as Strip Club Waitress

Eric Zuckerman as Kenny

Wally Dunn as Depository Clerk