Guest Stars Maren Heary as Dolly Holloway Frank Deal as Gary Levine Megan Sikora as Michelle Kessler Shiloh Fernandez as Tom Devins Blythe Danner as Nancy Kerry Condon as Melissa Saugraves Co Starring Ali Marsh as Blair Salz Quentin Mare as Adrian Salz Jordana Rose as Sadie Kessler Erin Neufer as Emily J.C. Montgomery as Principal Krappel Vardaan Arora as Raj Alok Tewari as Dr. Rothman Craig Wroe as Detective Chris Kelly