Raúl Castillo

Bernie

Mauricio Ochmann

Martin

Andrew Bachelor

Andrew

Malin Akerman

Lucy

Orlando Bloom

Tom

Jake Weber

Wally

Hannibal Buress

Jason

Emily Ratajkowski

Allison Lizowska

Jennifer Kim

Annie

Lawrence Michael Levine

Harrison

Joe Lo Truglio

Mike

Aubrey Plaza

Lindsay

Timothy Simons

Whitman

Parker Sawyers

Jason

Sam Guinan-Nyhart

Justin

Jasmine McNeely

Jeezy

Natasha Forouzannia

Masseuse

Karley Sciortino

Sally

Craig Butta

Frank Bruno

Siddhartha Rajan

Indian Client

Chris Doubek

Jay

Arsh Singh

Uber Passenger

Michaela Watkins

Karen Treska

Kate Berlant

Lauren

Spencer Parsons

Spencer Parsons

Judy Greer

Gretchen

Alex Ross Perry

Mr. Pope

Sophie Traub

Stephanie

Tim Kazurinsky

Father Timothy

Danny Masterson

Annie's Boyfriend

Nicky Excitement

Hugh

Hannah Ward

Hannah

Perry Myers

Detective Perry

Peter Gwinn

Andy

Michael Deal Jr.

Jaguar Creep

Beth Horn

Elysa

Marika Engelhardt

Detective Lindsay

Kayla Benegas

Host

Megan Ferguson

Easy

Jacqueline Toboni

Jo

Sophia Bush

Alexandria

Jaz Sinclair

Amber

Bing Liu

Bing

Cemre Paksoy

Alex

Odinaka Malachi Ezeokoli

Od

Kenzie Elizabeth

Kat

Kate Micucci

Annie

John Gallagher Jr.

Lucas

Kate Lyn Sheil

Annie's Roommate

Esteban Andres Cruz

Terrible Singing Date Guy

Dustin Guy Defa

Therapist

Cliff Chamberlain

Ryan

Stephanie Branco

Stacy

Lydia House

Lydia

Marc Maron

Jacob Malco

Jane Adams

Annabelle Jones

Melanie Lynskey

Beth

Grace Hahn

Coffee Shop Barista

Kali Skrap

Skrap

Anthony Smith

Ant

Elizabeth Reaser

Andi

Michael Chernus

Kyle

Kris Rey

Easy

T.J. Jagodowski

Bern

Dave Franco

Jeff

Zazie Beetz

Noelle

Aya Cash

Sherri

Evan Jonigkeit

Matt

Rebecca Spence

Cheryl

Gugu Mbatha-Raw

Sophie

Aislinn Derbez

Gabi

Jake Johnson

Drew

Lindsay Burdge

Amy

Danielle Macdonald

Grace

Kevin Lingle

Driver

Tyla Abercrumbie

Shelby

Kristina Valada-Viars

Alice

Marz Timms

Van Howard

Kiersey Clemons

Chase

Phil Ridarelli

Tom