Trailer
Cast
Jay Schmidt
Assistant Steve
Taye Diggs
Richard "Rick" Otis
Meredith Hagner
Becca
Pete Davidson
Duncan
Noah Robbins
Intern Bo
Doris McCarthy
Restaurant Guest
Fay Ann Lee
Kirsten's Friend Emma
Jeff Hiller
Mexican Restaurant Waiter
Jacqueline Honulik
Date
Anna Suzuki
Frantic Assistant Leslie
Cody Calafiore
Duncan's Hook-up
Sonia Denis
Ring Salesman
Tituss Burgess
Creepy Tim
Evan Parke
District Club Doorman
Fabrizio Brienza
Fancy Host
Stephanie Hsu
Nervous Assistant Amber
Annie Pisapia
Traveler
H. Foley
Lobby Delivery Guy
Buddy Bolton
Homeless Guy
Josh Berresford
Famous Athlete
Zoey Deutch
Harper Moore
Lucy Liu
Kirsten Stevens
Jon Rudnitsky
Mike
Stacey Alyse Cohen
Airport Security Officer - TSA
Kate Middleton
Mary
Leonard Ouzts
UPS Guy
Steve Beauchamp
Random Airport Traveler
Madison Arnold
Dennis
Glen Powell
Charlie Young
Jake Robinson
Golf Guy
Jaboukie Young-White
Assistant Alex
Wai Ching Ho
Kristen's Mom
Shana Solomon
Fancy Restaurant Waiter
Shyrley Rodriguez
Assistant Jamie
Serena Berman
Young Talented Writer
Patrick Holden O'Neill
Assistant Peter
Joan Smalls
Suze
Aaron Costa Ganis
Dan
Caitlin Brodnick
Assistant Anna