Guest Stars Chris Noth as Mr. Big Willie Garson as Stanford Blatch Ben Weber as Skipper Johnston Justin Theroux as Jared James McCaffrey as Max Caroline Aaron as Pamela Glock Jack Koenig as Michael Conway Co Starring Kate Jennings Grant as Alison Roth Deborah Zoe as Melissa John Scurti as Chunky Gay Guy 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