Olivia Wilde Director Kaitlyn Dever Amy Actor Beanie Feldstein Molly Actor Jessica Williams Miss Fine Actor Jason Sudeikis Principal Brown Actor Lisa Kudrow Charmaine Actor Will Forte Doug Actor Victoria Ruesga Ryan Actor Mason Gooding Nick Actor Skyler Gisondo Jared Actor Diana Silvers Hope Actor Molly Gordon Triple A Actor Billie Lourd Gigi Actor Eduardo Franco Theo Actor Nico Hiraga Tanner Actor Austin Crute Alan Actor Noah Galvin George Actor Michael Patrick O'Brien Pat the Pizza Guy Actor Ben Harris Yacht Waiter Actor Kyle Samples Butler Actor Deb Hiett George's Mom Actor Bluesy Burke Cindy Actor Christopher Avila Rob Actor Stephanie Styles Alison Actor John Hartman Yacht Waiter No. 2 Actor Adam Simon Krist Dick Actor Gideon Lang Skip Actor Ellen Doyle Murder Mystery Nurse Actor Katie Silberman Screenwriter, Producer Emily Halpern Screenwriter Sarah Haskins Screenwriter Susanna Fogel Screenwriter Megan Ellison Producer Jessica Elbaum Producer Chelsea Barnard Producer David Distenfeld Producer Will Ferrell Executive Producer Adam McKay Executive Producer Jillian Longnecker Executive Producer Scott Robertson Executive Producer Alex G. Scott Executive Producer Jason McCormick Cinematographer Brent White Film Editing Jamie Gross Film Editing Dan Nakamura Original Music Katie Byron Production Design Erika Toth Art Director Rachael Ferrara Set Decoration April Napier Costume Design Allison Jones Casting