Guest Stars Sarah Steele as Marissa Gold Anika Noni Rose as Wendy Scott-Carr Michael Ealy as Derrick Bond Gary Cole as Kurt McVeigh Jerry Strong as Matt Becker America Ferrera as Natalie Flores Dennis Boutsikaris as Tommy Segara Jennifer Lim as Diane's Assistant Jerry Stiller as Judge Felix Afterman Aaron Tveit as Jimmy Patrick Andrew Pang as Dr. Huang Graham Rowat as Damian Hart Leslie Kalarchian as Principal Athena Bruner