Guest Stars Mark Feuerstein as Mark Sarah Burns as Claire Adam Scott as Ben Josh Charles as Blake Eric Nenninger as Warner Rich Sommer as Graham Lake Bell as Donna David Wain as Yaron Samm Levine as Arty John Early as Logan Paul Scheer as Dave Chris Pine as Eric Jason Schwartzman as Greg Marlo Thomas as Vivian Co Starring Thaddeaus Ek as Nathan Chris Redd as Mason Andrea Rosen as Nadine Morgan Walsh as Tracy Cordelia Zawarski as Popular Girl #3 Daisy Stoneman as Popular Girl #2 Brett Manley as Willie / Young Reagan Kaycee Rice as Popular Girl #1