Guest Stars Chris Noth as Mr. Big Noelle Beck as Barbara Gerry Bamman as Shrink Joseph Murphy as Jack Co Starring Lisa Emery as Ruth / Mid 30's Woman Matthew Sussman as Wall Street Man Jonathan Walker as Ken Catherine Corpeny as Wife Sherri Alexander as Peacock Woman Laura Ekstrand as Plain Woman Amy Delucia as Beautiful Woman P.J. Heslin as Husband Toni James as Normal Woman Suzanne Smith as Long Island Woman Carmi Turchick as Scottie