Francesca Delbanco Diane Creator, Actor, Executive Producer Nicholas Stoller Creator, Executive Producer Rose Byrne Sylvia Actor, Executive Producer Seth Rogen Will Actor, Executive Producer Luke Macfarlane Charlie Greeves Actor Tre Hale Andy Actor Andrew Lopez Reggie Actor Sophie Leonard Frances Actor Carla Gallo Katie Actor Max Matenko Simon Actor Sophia Kopera Maeve Actor Milo Manheim Mason Grand Actor Vinny Thomas Omar Actor Guy Branum Stewart Actor Brock O'Hurn Koslo Actor Aidy Bryant Carrie Actor Michael Kostroff Frank Schaeffer Actor Danny Brown Lady Putteningham Actor Alisha Wainwright Audrey Actor Janet Varney Vanessa Actor Paul Lieberstein Dr. Melfi Actor O'Shea Read Producer James Weaver Executive Producer Conor Welch Executive Producer