Guest Stars Dominic Burgess as Jerry Summers Molly Griggs as Wendy Young Fredric Lehne as Don Duntsch Grainger Hines as Earl Burke Maryann Plunkett as Madeline Beyer Jennifer Kim as Stephanie Wu Dashiell Eaves as Stan Novak Cristala Carter as Shelley Brennan Carrie Preston as Robbie McClung Perry Strong as Joe Padua Diane Davis as Sarah Provost Co Starring Kelly Kirklyn as Dorothy Burke Shawn T. Andrew as Drew Sweeney Pilar Witherspoon as Dr. Ivers Sean Weil as Henry Aldrich Christine Pedi as Elaine Johnson Mark Torres as Judge Nesha Ward as Cindy Tremblay David Park as Director Earl Baker Jr. as Harold Brennan Jody Gleb as Janet Provost