Guest Stars Brian McNamara as Kyle Brooks Cynthia Stevenson as Dianne Brooks Reginald VelJohnson as Todd Stewart Skelton as Alumni #1 Charles Rahi Chun as Simon 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 Dee Baldus as Gertrude Franc Ross as Clinic Doctor Joshua Alba as Student #1 John Furey as Dennis Cutter Garcia as Uniform Cop