Chris Pine as Sam Harper

Elizabeth Banks as Frankie Davis

Olivia Wilde as Hannah

Michelle Pfeiffer as Lillian Harper

Mark Duplass as Ted

Devin Brochu as Simon

Barbara Eve Harris as Mrs. Haney

Dean Chekvala as Jerry

Sara Mornell as Dr. Amanda Goldstein

Michael Hall D'Addario as Josh Alan Davis

Philip Baker Hall as Ike Rafferty

David Burrus as Derek

Joseph Wise as Danny

Gabriela Milla as Lucy

Abhi Sinha as Manager

Jon Favreau as Richards

Rob Brownstein as Sales VP Ben

Katy Boyer as Lillian's Friend

Katherine Sigismund as Lillian's Friend

Sheila Shaw as Lillian's Friend

Darren O'Hare as Telemarketer

Maximilian Osinski as Telemarketer

Christiann Castellanos as Secretary

LeShay N. Tomlinson as Attendant

Tara Inden as LAX Flight Attendant

Liza del Mundo as Receptionist

Paul Sanchez as AA Group Leader

Stephanie Bast as AA Member

Ken Barnett as AA Member

Shaughn Buchholz as AA Member

Pippa Hinchley as AA Member

David Kelsey as AA Member

Nick Smoke as AA Member

Amanda Young as AA Member

David Zyler as 70's Studio Tech

Rif Hutton as 70's Studio Tech

Moosie Drier as 70's Studio Tech

Steve Alterman as 70's Studio Tech

Jon Morgan Woodward as John - AA Member (uncredited)