James Wolk Joe Kimbreau Actor Natalie Martinez Amy Kindelán Actor Elizabeth Lail Jenny Banks Actor Charlie Barnett Eric Payne Actor Anne Ramsay Gwen Kimbreau Guest Star David Warshofsky Frank Kimbreau Guest Star John Gluck Christopher Kimbreau Guest Star Brandon Sutton Barrett Blankenship Guest Star Joe Carroll Ray Jaffin Guest Star Gabrielle Byndloss Mallory Guest Star Christine Adams Regina Diaz Guest Star Michelle Lukiman Kokoro Guest Star Lili Mirojnick Kinsley Guest Star Reinaldo Faberlle Miguel Turner Guest Star Elizabeth Becka Professor Holland Guest Star Russel Friend Executive Producer Garrett Lerner Executive Producer Matt Reeves Executive Producer Adam Kassan Executive Producer Rafi Crohn Executive Producer Howard Klein Executive Producer Adam Davidson Executive Producer Chris Koch Director Simran Baidwan Writer Ian Deitchman Writer Kristin Rusk Robinson Writer