Guest Stars Willie Garson as Stanford Blatch Jennifer Guthrie as Patience Co Starring H. Jon Benjamin as Jeff Joanna P. Adler as Syd Isabel Gillies as Elaine John Connolly as David Peter Reardon as Paul Remy Auberjonois as Waiter Melora Griffis as Young 30's Woman Kristen Behrendt as Rebecca Karen Braga as Intellectual Woman Kerrianne Spellman as Anne David Healy as Peter Karl Geary as Tommy David Forsyth as Senior Partner "Chip" Scott Rabinowitz as Sean Lou Liberatore as Lou Peter Rini as Joe Andrew Fiscella as Working Class Guy Stephanie Venditto as Lisa