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 Sarah Sokolovic as Tori Bachman Douglas Smith as Corey Brockfield Crystal Fox as Elizabeth Howard Tim True as Detective Walt Gibson Martin Donovan as Martin Howard Denis O'Hare as Ira Farber Khalilah Joi as Young Elizabeth Mykal-Michelle Harris as Young Bonnie Poorna Jagannathan as Katie Richmond Becky Ann Baker as Judge Marylin Ciprian Eliza Shin as Vice Principal Coolidge Travis Schuldt as Michael Something Bellina Logan as Mindy Deb Snyder as Marsha Paul Nygro as Kevin's Partner Mike Bradecich as Carl Swallow Feodor Chin as Kevin Benjamin Plessala as Brian Melinda Ratner as Esalen Wife Will Hawkes as Esalen Husband