Charlie

Aaron Tveit

Brice

Kal Penn

Brad

Jason Ralph

Angela

Abby Elliott

Vince (as Shane Mcrae)

Shane McRae

Anne

Annaleigh Ashford

Kathy

Lauren Miller Rogen

Angela's Dad

Chris Elliott

Lorelei

Kelen Coleman

Charlie's Therapist

Lewis Black

Angela's Mom

Haviland Morris

Mary

Jessica Rothe

Nathan

Ben Rappaport

Workaholic Hottie

Julia Eringer

Frat Guy Manager

Zack Robidas

Evy

Elizabeth Alderfer

Governor Kelleher

Jason Jones

Date #3

Emily Althaus

Date #2

Vasthy Mompoint

Unemployment Worker

Constance Shulman

Date #1

Liz Holtan

Magic 8-Ball Manager

Jake Paque

Date #4

Sulekha Naidu

Mr. Tucker/Angry Wedding Guest

Brian Russell

Edward Hart

Jason Altman

Professor

John Quilty

Downtown Man

Reggie Green

Presidential Debate Moderator

Deidre Goodwin

Well-Spoken Beastly Thug

Jason Alan Carvell

Monotone Manager

Sekou Laidlow

Mr. Staut

Ezra Barnes

Sorority Girl

Nichole Bloom

Barry/Trust Funded Avenger

Brooks Wheelan

Wedding Bartender

Matthew Robbins

Juice Barista

Brittnew Lewis