Guest Stars Samantha Sloyan as Dr. Penelope Blake Wilmer Valderrama as Kyle Diaz Rebecca McFarland as Tara Parker Morgan Lily as Jennifer "Jenny" Parker Vanessa Bell Calloway as Lucinda Gamble Anne-Marie Johnson as Judge Madeline Kane Gwendoline Yeo as Michelle Carpio Stephen Mendel as Dr. Russo Co Starring Eva Ariel Binder as Sofia Robbins-Sloan-Torres Eliyas Qureshi as Bailiff