Guest Stars Darby Camp as Chloe Mackenzie Chloe Coleman as Skye Carlson Cameron Crovetti as Josh Wright Nicholas Crovetti as Max Wright Ivy George as Amabella Klein Santiago Cabrera as Joseph Bachman Merrin Dungey as Detective Adrienne Quinlan P.J. Byrne as Principal Nippal Douglas Smith as Corey Brockfield Sarah Sokolovic as Tori Bachman Crystal Fox as Elizabeth Howard Tim True as Detective Walt Gibson 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 Eliza Shin as Vice Principal Coolidge Becky Ann Baker as Judge Marylin Ciprian Travis Schuldt as Michael Something Feodor Chin as Kevin Bellina Logan as Mindy Paul Nygro as Kevin's Partner Deb Snyder as Marsha Mike Bradecich as Carl Swallow Benjamin Plessala as Brian Melinda Ratner as Esalen Wife Will Hawkes as Esalen Husband