Guest Stars Reginald VelJohnson as Todd Cynthia Stevenson as Dianne Brooks John Furey as Dennis Brian McNamara as Kyle Brooks Charles Rahi Chun as Simon Stewart Skelton as Alumni #1 Dee Baldus as Gertrude Milda Dacys as Juliette Rafael Kalichstein as Bartender Oliver Macready as Drew Cooney Nicola Hersh as Mrs. Rutherford Lindy Newton as Young Trudy Kyle Kulish as Alumni #2 Charles Laulette as Alumni Husband Alex Cohen as Delivery Man Luiggi Debiasse as Young Monk Glenda Morgan Brown as Alumni Wife Loanne Bishop as Alumni Chairwoman Franc Ross as Clinic Doctor Joshua Alba as Student #1 Cutter Garcia as Uniform Cop