Justin Spitzer Creator, Executive Producer Ana Gasteyer Katherine Actor Jon Barinholtz Wesley Actor Harriet Dyer Sadie Actor Humphrey Ker Elliot Actor Michael Benjamin Washington Cyrus Actor Tye White Jack Actor X Mayo Dori Actor Elizabeth Hinkler Chloe Guest Star Caitlin Kimball Phoebe Guest Star Tirosh Schneider Joshua Guest Star Natalie Cabo Harper Guest Star David Theune Tom Guest Star Korama Danquah Allison Guest Star Sara Sevigny Joy Guest Star Pam Trotter Elaine Guest Star Jennifer Shelton HR Video Narrator Guest Star Abigail Kate Thomas Ruby Guest Star Meighan La Rocca Mandy Guest Star Jeffrey Blitz Executive Producer Aaron Kaplan Executive Producer Dana Honor Executive Producer Lara Everly Director Elena Crevello Writer