Guest Stars Darby Camp as Chloe Mackenzie Chloe Coleman as Skye Carlson Nicholas Crovetti as Max Wright Cameron Crovetti as Josh 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 Becky Ann Baker as Judge Marylin Ciprian Poorna Jagannathan as Katie Richmond Eve Gordon as Dr. Danielle Cortland James Trevena-Brown as Brad Gorcey Brayden McDonell as 3-Year-Old Josh Asher McDonell as 3-Year-Old Max Goreti Da Silva as Clerk Chad Mountain as Bailiff Adam Cropper as Cashier Maverick Thompson as Raymond Teddy Blum as Young Perry Taylor Treadwell as Young Mary Louise