Guest Stars Theo Stockman as Jacob Cricket Brown as Chloe Morgan Troy Iwata as Damian Saito Steven Boyer as Matthew Peter Jacobson as Robert Paltrow Ceci Fernandez as Vanessa Jake Levy as Aaron Arnie Burton as Teacher Leon Addison Brown as Judge Co Starring Shanti Ashanti as Adi Bianca Norwood as Ryan David Ebert as WeWork Exec 1 / Jeff Winitsky Carolyn Baeumler as Rebekah's Mom Angela Wong Carbone as Lucy Jaiden Klein as Tween Rebekah Kenneth De Abrew as Scene Partner Gaelen Gilliland as Bank Teller Wonu Ogunfowora as H.R. Onboarding Assistant Kim Fischer as Mark Trevor James Berger as Keith Paltrow Sofia Dobrushin as Andrea
