Guest Stars Timothy Granaderos as Montgomery De La Cruz Josh Hamilton as Matt Jensen Steven Weber as Principal Gary Bolan Bryce Cass as Cyrus RJ Brown as Caleb Brenda Strong as Nora Walker Joseph C. Phillips as Greg Davis Anne Winters as Chlöe Rice Wilson Cruz as Dennis Vasquez Tommy Dorfman as Ryan Shaver Chelsea Alden as Mackenzie Samantha Logan as Nina Jones Allison Miller as Sonya Struhl Kelli O'Hara as Jackie Jake Weber as Barry Walker Keiko Agena as Pam Bradley Jackie Geary as Amber Foley Kimiko Gelman as Vice Principal Jane Child Brittany Perry-Russell as Dre Porter Makenzie Vega as Sarah Carlin Co Starring Brandon Butler as Scott Reed Richard Gross as Judge Campbell Spence Moore II as Michael Jeanette Pavini as Maureen Carlin Gigi Benson as Ms. Paul