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 Guest Star Ashley Wolff Jenna Guest Star Alek C. Unszusz Irving Rosenblatt Guest Star Amarr M. Wooten Buddy Guest Star Kelly Albanese Kelly Guest Star Lars Slind Ronald Guest Star Mimi Karsch Narducci Dancer Guest Star Justin Adler Executive Producer Aaron Kaplan Executive Producer Jason Winer Executive Producer Jeffrey Morton Executive Producer Maggie Mull Writer Rebecca Asher Director