Guest Stars Greg Ellis as Simon Cochran Kathleen Rose Perkins as Amy Vanessa Marano as Haley McGuire Uriah Shelton as Jack McGuire Adam Scott as Josh Burkett Tim Russ as Gordon Benedict John Getz as Peter Derby Jason O'Mara as Stu Hoffman Bob Morrisey as 50-Year-Old Dad Adilah Barnes as Librarian Jeff Witzke as Focus Group Moderator Sally Ann Brooks as Single Mom Shane Edelman as Accountant Co Starring Ben Carroll as Mourner #2 Lara Phillips as Mourner #1 Laurie Searle as Mourner #3 Jon Mayes as Mail Guy