Guest Stars Marylouise Burke as Jessica's Mother Alanna Ubach as Yael Koontz Lennie James as Charlie Gina Hecht as Principal Rhonda Barr Kathryn Hahn as Claire Ludmila Velikaya as Lottie's friend Elisa Perry as Prostitute #2 Eileen Grubba as Missy Verda Bridges as Prostitute #3