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