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 Josh Groban Ian Guest Star Kat Von D Lois Guest Star Hunter King Clementine Guest Star Jordan Danger Host Guest Star Andrew Patrick Ralston Chip Baggins Guest Star Elsa Ramon Reporter Guest Star Lola Blanc Girl Guest Star Justin Adler Executive Producer Aaron Kaplan Executive Producer Jason Winer Executive Producer, Director Jeffrey Morton Executive Producer Alec Sulkin Writer