- Raúl Castillo - Bernie
- Mauricio Ochmann - Martin
- Andrew Bachelor - Andrew
- Malin Åkerman - 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
- 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
- Peter Gwinn - Andy
- Beth Horn - Elysa
- Marika Engelhardt - Detective Lindsay
- Megan Ferguson - Samantha
- Megan Ferguson - Easy
- Jacqueline Toboni - Jo
- Sophia Bush - Alexandria
- Jaz Sinclair - Amber
- Liu Bing - Bing
- Odinaka Malachi Ezeokoli - Od
- 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
- Marc Maron - Jacob Malco
- Jane Adams - Annabelle Jones
- Melanie Lynskey - Beth
- 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
- Kiersey Clemons - Chase
- Phil Ridarelli - Tom
- Stephen George - Jo's Partner
- Jane Brody - Ethics Professor
- Suzanne Adent - Penny
- Cassidy Slaughter-Mason - Megan
- Lucas Von Kampen - Alan
- Lucas Von Kampen - Allen
- Clare O'Connor - Amanda
- Victoria Allen - Ashley
Jake Weber hace el papel de Wally.
Orlando Bloom interpreta a Tom en la serie.
Craig Butta interpreta a Frank Bruno en la serie.
Peter Gwinn interpreta a Andy en la serie.
Megan Ferguson interpreta a Samantha en la serie.
Jacqueline Toboni hace el papel de Jo.
Jaz Sinclair hace el papel de Amber.
Odinaka Malachi Ezeokoli interpreta a Od en la serie.
Kate Micucci hace el papel de Annie.
Kate Lyn Sheil interpreta a Annie's Roommate en la serie.
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