Guest Stars Josh Hamilton as Matt Jensen Mark Pellegrino as Officer Bill Standall Steven Weber as Principal Gary Bolan Michele Selene Ang as Courtney Crimsen Brian d'Arcy James as Andy Baker Steven Silver as Marcus Cole Brandon Larracuente as Jeff Atkins Robert Gant as Todd Crimsen Alex Quijano as Steve Crimsen Co Starring Timothy Granaderos as Montgomery De La Cruz Tommy Dorfman as Ryan Shaver Karen Kahn as Secretary Gabrielle Haugh as Laura Hannah Payne as Stephanie Hannah Perko-Engel as Other Girl Ellen Ho as Ashley Danielle O'Dea as Theresa the Barista Desiree Choy as Girl #2