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 Jordan Peele Chad Guest Star Ashley Wolff Jenna Guest Star Susan Park Dr. Sally Hong Guest Star Pamela Trotter Shannon Guest Star Ann Morgan Guilbert GiGi Guest Star Hunter King Clementine Guest Star Martin Mull Gary Tompkins Guest Star Bella Shepard Lexie Guest Star Jerry Lambert Chase Guest Star Jason Winer Executive Producer, Director Justin Adler Executive Producer, Writer Aaron Kaplan Executive Producer Jeffrey Morton Executive Producer Barbie Feldman Writer Lesley Wake Writer Elizabeth Tippet Writer Alec Sulkin Writer Joe Cristalli Writer Maggie Mull Writer Greg Malins Writer Kirker Butler Writer Phil Trail Director Chad Lowe Director Ken Whittingham Director Phil Traill Director Helen Hunt Director Rolin Jones Writer