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Glen Powell

Charlie Young

Zoey Deutch

Harper Moore

Taye Diggs

Richard "Rick" Otis

Joan Smalls

Suze

Meredith Hagner

Becca

Lucy Liu

Kirsten Stevens

Pete Davidson

Duncan

Jon Rudnitsky

Mike

Tituss Burgess

Creepy Tim

Noah Robbins

Intern Bo

Jaboukie Young-White

Assistant Alex

Jake Robinson

Golf Guy

Aaron Costa Ganis

Dan

Wai Ching Ho

Kristen's Mom

Jeff Hiller

Mexican Restaurant Waiter

Evan Parke

District Club Doorman

Doris McCarthy

Restaurant Guest

Stacey Alyse Cohen

Airport Security Officer - TSA

Shana Solomon

Fancy Restaurant Waiter

Fabrizio Brienza

Fancy Host

Shyrley Rodriguez

Assistant Jamie

Jacqueline Honulik

Date

Anna Suzuki

Frantic Assistant Leslie

Stephanie Hsu

Nervous Assistant Amber

Kate Middleton

Mary

Annie Pisapia

Traveler

Cody Calafiore

Duncan's Hook-up

Leonard Ouzts

UPS Guy

Paulie Deo Jr.

Tim

Ralph Byers

Frank

Jay Schmidt

Assistant Steve

Serena Berman

Young Talented Writer

Hazel Anne Raymundo

Sweet Mother

Alejandro Hernandez

Bobby the Nacho Guy

Madison Arnold

Dennis

Sonia Denis

Ring Salesman

Fay Ann Lee

Kirsten's Friend Emma

Jackie Burns

Kirsten's Friend Sloane

Steve Beauchamp

Random Airport Traveler

Patrick Holden O'Neill

Assistant Peter

Jamie Forbes

Assistant James

Caitlin Brodnick

Assistant Anna

Nick Cafero

Assistant George

Matt Gehring

Assistant on the Phone

Matt Bailey

Tom

H. Foley

Lobby Delivery Guy

Buddy Bolton

Homeless Guy

Saul Alvarez

Pizza Delivery Guy

Leah Lauren

Tourist

Keldrick La Vott Crowder

Yankee Fan

Josh Berresford

Famous Athlete