Aaron Tveit as Charlie Carroll

Kal Penn as Brice

Abby Elliott as Angela

Annaleigh Ashford as Anne

Kelen Coleman as Lorelei

Haviland Morris as Angela's Mom

Chris Elliott as Angela's Dad

Lauren Miller Rogen as Kathy

Jessica Rothe as Mary

Lewis Black as Charlie's Therapist

Shane McRae as Vince (as Shane Mcrae)

Julia Eringer as Workaholic Hottie

Misty Gonzalez as Background

Scott Hedley as Presidential Debate Attendee

Emily Althaus as Date #3

Vasthy Mompoint as Date #2

Liz Holtan as Date #1

Guy Olivieri as Restaurant Worker

Jake Paque as Magic 8-Ball Manager

Sulekha Naidu as Date #4