Guest Stars Mark Feuerstein as Mark Adam Scott as Ben Sarah Burns as Claire Rich Sommer as Graham Eric Nenninger as Warner Josh Charles as Blake Lake Bell as Donna John Early as Logan David Wain as Yaron Samm Levine as Arty Chris Pine as Eric Paul Scheer as Dave Jason Schwartzman as Greg Marlo Thomas as Vivian Co Starring Thaddeaus Ek as Nathan Andrea Rosen as Nadine Chris Redd as Mason 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