Guest Stars Chris Noth as Mr. Big Willie Garson as Stanford Blatch Ben Weber as Skipper Johnston Justin Theroux as Jared Caroline Aaron as Pamela Glock James McCaffrey as Max Jack Koenig as Michael Conway Co Starring Kate Jennings Grant as Alison Roth John Scurti as Chunky Gay Guy Deborah Zoe as Melissa Michael Spiller as Slick Guy Susan Malfitano as Ordinary Woman Todd Barry as Ordinary Guy Michael Dale as Rick Connelly Avalon Hodges as Julia Melissa Darling as Almost Together Woman