Guest Stars Dominic Burgess as Jerry Summers Fredric Lehne as Don Duntsch Molly Griggs as Wendy Young Grainger Hines as Earl Burke Jennifer Kim as Stephanie Wu Maryann Plunkett as Madeline Beyer 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 Earl Baker Jr. as Harold Brennan David Park as Director Jody Gleb as Janet Provost