Glen Powell as Charlie Young

Zoey Deutch as Harper Moore

Taye Diggs as Richard "Rick" Otis

Joan Smalls as Suze

Meredith Hagner as Becca

Lucy Liu as Kirsten Stevens

Pete Davidson as Duncan

Jon Rudnitsky as Mike

Tituss Burgess as Creepy Tim

Noah Robbins as Intern Bo

Jaboukie Young-White as Assistant Alex

Jake Robinson as Golf Guy

Aaron Costa Ganis as Dan

Wai Ching Ho as Kristen's Mom

Jeff Hiller as Mexican Restaurant Waiter

Evan Parke as District Club Doorman

Doris McCarthy as Restaurant Guest

Stacey Alyse Cohen as Airport Security Officer - TSA

Shana Solomon as Fancy Restaurant Waiter

Fabrizio Brienza as Fancy Host

Shyrley Rodriguez as Assistant Jamie

Jacqueline Honulik as Date

Anna Suzuki as Frantic Assistant Leslie

Stephanie Hsu as Nervous Assistant Amber

Kate Middleton as Mary

Annie Pisapia as Traveler

Cody Calafiore as Duncan's Hook-up

Leonard Ouzts as UPS Guy

Paulie Deo Jr. as Tim

Ralph Byers as Frank

Jay Schmidt as Assistant Steve

Serena Berman as Young Talented Writer

Hazel Anne Raymundo as Sweet Mother

Alejandro Hernandez as Bobby the Nacho Guy

Madison Arnold as Dennis

Sonia Denis as Ring Salesman

Fay Ann Lee as Kirsten's Friend Emma

Jackie Burns as Kirsten's Friend Sloane

Steve Beauchamp as Random Airport Traveler

Patrick Holden O'Neill as Assistant Peter

Jamie Forbes as Assistant James

Caitlin Brodnick as Assistant Anna

Nick Cafero as Assistant George

Matt Gehring as Assistant on the Phone

Matt Bailey as Tom

H. Foley as Lobby Delivery Guy

Buddy Bolton as Homeless Guy

Saul Alvarez as Pizza Delivery Guy

Leah Lauren as Tourist

Keldrick La Vott Crowder as Yankee Fan

Josh Berresford as Famous Athlete