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 Megan Mullally Mary-Lynn Guest Star Nick Offerman Spencer Guest Star Fortune Feimster Dougie Guest Star Leith M. Burke Dr. Casey Dia Guest Star Justin Adler Executive Producer, Writer Aaron Kaplan Executive Producer Jason Winer Executive Producer, Director Jeffrey Morton Executive Producer