Guest Stars Olivia Nikkanen as Gwen Jack Mulhern as Grizz 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 Chloë Levine as Emily Anastasia Barzee as Karen David Aaron Baker as Jim Pressman Kate Avallone as Mazie Bates Wilder as Will's Father Michael Siberry as Rodgers Eliot Paul Anthony Stewart as Doug Eliot Ava Gaudet as Lynette Eliot Angela Hope Smith as Assistant Carly Nahon as Gina Bria D'Aguanno as Millicent