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 Molly Shannon Allie Guest Star Angela Kinsey Ruth Guest Star Leslie David Baker Gavin Guest Star Gillian Vigman Tabitha Guest Star Justin Adler Executive Producer Aaron Kaplan Executive Producer Jason Winer Executive Producer Jeffrey Morton Executive Producer Barbie Feldman Writer Alisa Statman Director