Dianne Wiest Joan Actor James Brolin John Actor Zoe Lister Jones Jen Actor Colin Hanks Greg Actor Angelique Cabral Colleen Actor Thomas Sadoski Matt Actor Betsy Brandt Heather Actor Dan Bakkedahl Tim Actor Niall Cunningham Tyler Actor Holly J. Barrett Samantha Actor Giselle Eisenberg Sophia Actor Hunter King Clementine Actor Kurt Warner Himself Guest Star Glenn Rockowitz Stadium Announcer Guest Star Malika Williams Stadium Representative Guest Star Bob Wiltfong Football Fan Guest Star Kim Yarbrough Salesperson Guest Star Justin Adler Executive Producer Aaron Kaplan Executive Producer Jason Winer Executive Producer Jeffrey Morton Executive Producer Elizabeth Tippet Writer James Alan Hensz Director