Guest Stars Jack Mulhern as Grizz Olivia Nikkanen as Gwen Salena Qureshi as Bean Emilio Garcia-Sanchez as Jason Spencer House as Clark Kiara Pichardo as Madison Grace Victoria Cox as Lexie Naomi Oliver as Olivia Kelly Rose Golden as Marnie Alicia Crowder as Erika Benjamin Breault as Blake Seth Meriwether as Greg Dewey Acei Martin as Tiffany Amy Carlson as Amanda Pressman Chaske Spencer as Mr. Pfeiffer Anastasia Barzee as Karen Chloë Levine as Emily David Aaron Baker as Jim Pressman Paul Anthony Stewart as Doug Eliot Kate Avallone as Mazie Bates Wilder as Will's Father Michael Siberry as Rodgers Eliot Ava Gaudet as Lynette Eliot Angela Hope Smith as Assistant Carly Nahon as Gina Bria D'Aguanno as Millicent