Owen Wilson as John Grogan

Jennifer Aniston as Jennifer Grogan

Eric Dane as Sebastian Tunney

Kathleen Turner as Ms. Kornblut

Alan Arkin as Arnie Klein

Nathan Gamble as Patrick (Age 10)

Haley Bennett as Lisa

Haley Higgins as Shannon

Ann Dowd as Dr. Platt

Clarke Peters as Editor

Finley Jacobsen as Conor (Age 8)

Lucy Merriam as Colleen (Age 5)

Bryce Robinson as Patrick (Age 7)

Ben Hyland as Conor (Age 5)

Sarah O'Kelly as Neighbor Mom (Nurse)

Keith Hudson as Big Guy

Haley Hudson as Debby

Tom Irwin as Dr. Sherman

Alec Mapa as Jorge

Sandy Martin as Lori

Joyce Van Patten as Mrs. Butterly

Zabryna Guevara as OB-GYN Nurse

Megan Grace as Secretary

Ana Ayora as Viviana

Matthew J. Walters as Billy

Nicole Herold as Sunbather

Paul Tei as Dude

Gaston Renaud as Metro Reporter

Angelina Assereto as Waitress

Emmett Robin as Boy

Lisa Varga as Still Photographer

Dylan Henry as Patrick (Age 3)

Stephen Lee Davis as Neighbor Steve

Michael Baskin as Party Guy Michael

Bradley Frishman as Patrick (Age 20 Months)

Eric Conger as Newscaster

Clyde the Dog as Adult Marley