Cameron Diaz as Elizabeth Halsey

Justin Timberlake as Scott Delacorte

Jason Segel as Russell Gettis

Lucy Punch as Amy Squirrel

Phyllis Smith as Lynn Davies

Kaitlyn Dever as Sasha Abernathy

John Michael Higgins as Principal Wally Snur

Thomas Lennon as Carl Halabi

Kathryn Newton as Chase Rubin-Rosse

Molly Shannon as Melody (Garrett's Mom)

Eric Stonestreet as Kirk

Matthew J. Evans as Garrett Tiara

Dave Allen as Sandy Pinkus

Jillian Armenante as Ms. Pavicic

Igal Ben Yair as Arkady

Aja Bair as Devon (Chase's Friend)

Andra Nechita as Gaby

Noah Munck as Tristan

FINNEAS as Spencer

Daniel Castro as Rodrigo (Acne Kid)

Deirdre Lovejoy as Sasha's Mother

Adrian Kali Turner as Shawn

Paul Bates as School Superintendent

Jeff Judah as Janitor

Nat Faxon as Mark

Stephanie Faracy as Mrs. Pubich

David Paymer as Doctor Vogel

Alanna Ubach as Angela

Christine Smith as Danni

Paul Feig as Dad at Carwash

Melvin Mar as Male Teacher (Bathroom)

Rose Abdoo as School Secretary

Jerry Lambert as Morgan's Dad

Jennifer Irwin as Chase's Mom

Christopher Rockwell as Chase's Dad

David Doty as Armando the Homeless Guy

Rick Overton as Philip

Danny Trapp as Cowboy at Palace

Matt Besser as Abraham Lincoln (Tour Guide)

Lee Eisenberg as Blacksmith (Re-Enactor)

Bruno Gunn as Police Officer

Jordan Van Vranken as Crying Girl

Kadee Noel Brown as Student in Elizabeth's Class (uncredited)

Jennifer Holloway as Sheila (uncredited)

Christina Gabrielle as 8th Grade Student (uncredited)