Guest Stars Cameron Crovetti as Josh Wright Darby Camp as Chloe Mackenzie Chloe Coleman as Skye Carlson Nicholas Crovetti as Max Wright Ivy George as Amabella Klein Douglas Smith as Corey Brockfield Crystal Fox as Elizabeth Howard Martin Donovan as Martin Howard Denis O'Hare as Ira Farber Mykal-Michelle Harris as Young Bonnie Khalilah Joi as Young Elizabeth Poorna Jagannathan as Katie Richmond Eve Gordon as Dr. Danielle Cortland Becky Ann Baker as Judge Marylin Ciprian James Trevena-Brown as Brad Gorcey Chad Mountain as Bailiff Brayden McDonell as 3-Year-Old Josh Asher McDonell as 3-Year-Old Max Goreti Da Silva as Clerk Adam Cropper as Cashier Maverick Thompson as Raymond Teddy Blum as Young Perry Taylor Treadwell as Young Mary Louise