Guest Stars Maya Stojan as Tory Ellis Melise as Hillary Cooper Sam Anderson as Principal Duncan Cas Anvar as Dr. Rampanel Hannah Marks as Jordan Gibbs Jackie Debatin as Realtor Lori Alan as Ms. Papen Victory Van Tuyl as Kris Howard Julie Pinson as Diane Beaumont Leigh Parker as Lucas Troy Arianna Ortiz as Librarian John Mese as Mr. Charles Beaumont Co Starring Natasha Hall as Madison Beaumont Liz Benoit as Assistant Will Deutsch as Nerdy Guy Sam Towers as Riley Mitchum Uncredited LaTeasha Leigh Clark as Party Goer