Don't Think Twice

Keegan-Michael Key

Jack

Gillian Jacobs

Samantha

Chris Gethard

Bill

Kate Micucci

Allison

Tami Sagher

Lindsay

Mike Birbiglia

Miles

Richard Masur

Lou

Sondra James

Bonnie

Richard Kline

Mr. Coughlin

Emily Skeggs

Shy Sarah

Brandon Scott Jones

Audience Chuck

Sunita Mani

Amy

Glenn Wein

Psychiatrist

Neil Fleischer

Pianist Seth

Erin Darke

Natasha

Gary Richardson

Gary

Steve Waltien

Hugh Finn

Kati Rediger

Alicia Bonham

Hallie Bulleit

Audience Claudia

Garth Kravits

Doctor

Jason C. Brown

Studio Page

Pete Holmes

Self

Seth Barrish

Timothy

Miranda Bailey

Producer