Zoey Deutch character Harper Moore
Glen Powell character Charlie Young
Lucy Liu character Kirsten Stevens
Taye Diggs character Richard "Rick" Otis
Joan Smalls character Suze
Meredith Hagner character Becca
Pete Davidson character Duncan
Jon Rudnitsky character Mike
Tituss Burgess character Creepy Tim
Noah Robbins character Intern Bo
Jaboukie Young-White character Assistant Alex
Jake Robinson character Golf Guy
Aaron Costa Ganis character Dan
Ching Hoh-Wai character Kristen's Mom
Jeff Hiller character Mexican Restaurant Waiter
Evan Parke character District Club Doorman
Doris McCarthy character Restaurant Guest
Stacey Alyse Cohen character Airport Security Officer - TSA
Shana Solomon character Fancy Restaurant Waiter
Fabrizio Brienza character Fancy Host
Shyrley Rodriguez character Assistant Jamie
Jacqueline Honulik character Date
Anna Suzuki character Frantic Assistant Leslie
Stephanie Hsu character Nervous Assistant Amber
Kate Middleton character Mary
Annie Pisapia character Traveler
Cody Calafiore character Duncan's Hook-up
Leonard Ouzts character UPS Guy
Paulie Deo Jr. character Tim
Ralph Byers character Frank
Faith Logan character Elegant Restaurant Patron (uncredited)