Annie

Elizabeth Reaser

Annabelle Jones

Jane Adams

Bernie

Raul Castillo

Noelle

Zazie Beetz

Kyle

Michael Chernus

Jason

Hannibal Buress

Gabi

Aislinn Derbez

Amber

Jaz Sinclair

Jo

Jacqueline Toboni

Martin

Mauricio Ochmann

Annie

Kate Micucci

Sherri

Aya Cash

Cheryl

Rebecca Spence

Drew

Jake Johnson

Alexandra

Alexandra Marzella

Jeff

Dave Franco

Chase

Kiersey Clemons

Dave

David Pasquesi

Matt

Evan Jonigkeit

Wally

Jake Weber

Lindsay

Aubrey Plaza

Gretchen

Judy Greer

Lauren

Kate Berlant

Amy

Lindsay Burdge

Tom

Orlando Bloom

Lucy

Malin Akerman

Jacob Malco

Marc Maron

Therapist

Dustin Guy Defa

Allison Lizowska

Emily Ratajkowski

Andrew

Andrew Bachelor

Penny

Suzanne Adent

Sophie

Gugu Mbatha-Raw

Frank Bruno

Craig Butta

Andy

Peter Gwinn

Easy / Samantha

Megan Ferguson

Od

Odinaka Malachi Ezeokoli

Annie's Roommate

Kate Lyn Sheil

Ryan

Cliff Chamberlain

Grace

Danielle Macdonald

Alice

Kristina Valada-Viars

Allen

Lucas Von Kampen

Annie

Jennifer Kim

Harrison

Lawrence Michael Levine

Mike

Joe Lo Truglio

Whitman

Timothy Simons

Jason

Parker Sawyers

Justin

Sam Guinan-Nyhart

Jeezy

Jasmine McNeely

Masseuse

Natasha Forouzannia

Sally

Karley Sciortino

Indian Client

Siddhartha Rajan

Jay

Chris Doubek

Uber Passenger

Arsh Singh

Karen Treska

Michaela Watkins

Spencer Parsons

Spencer Parsons

Mr. Pope

Alex Ross Perry

Stephanie

Sophie Traub

Father Timothy

Tim Kazurinsky

Annie's Boyfriend

Danny Masterson

Hugh

Nicky Excitement

Hannah

Hannah Ward

Detective Perry

Perry Myers

Jaguar Creep

Michael Deal Jr.

Elysa

Beth Horn

Detective Lindsay

Marika Engelhardt

Host

Kayla Benegas

Alexandria

Sophia Bush

Bing

Bing Liu

Alex

Cemre Paksoy

Kat

Kenzie Elizabeth

Lucas

John Gallagher Jr.

Terrible Singing Date Guy

Esteban Andres Cruz

Stacy

Stephanie Branco

Lydia

Lydia House

Beth

Melanie Lynskey

Coffee Shop Barista

Grace Hahn

Skrap

Kali Skrap

Ant

Anthony Smith

Easy

Kris Rey

Bern

T.J. Jagodowski

Driver

Kevin Lingle

Shelby

Tyla Abercrumbie

Van Howard

Marz Timms

Tom

Phil Ridarelli

Jo's Partner

Stephen George

Ethics Professor

Jane Brody

Waitress

Brennan Stacker

Megan

Cassidy Slaughter-Mason

Amanda

Clare O'Connor

Ashley

Victoria Allen