Guest Stars Willie Garson as Stanford Blatch Jennifer Guthrie as Patience Co Starring Joanna P. Adler as Syd H. Jon Benjamin as Jeff Peter Rini as Joe Isabel Gillies as Elaine 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 John Connolly as David David Forsyth as Senior Partner "Chip" Scott Rabinowitz as Sean Lou Liberatore as Lou Andrew Fiscella as Working Class Guy Stephanie Venditto as Lisa