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 Padma Lakshmi Stephanie Guest Star Ana Sophia Heger Lark Guest Star Kat Purgal Employee Guest Star Zach Reino Class Member Guest Star John Funk Golfer Guest Star Justin Adler Executive Producer Aaron Kaplan Executive Producer Jason Winer Executive Producer Jeffrey Morton Executive Producer Jordan Young Writer Jonathan Judge Director