George urges Jonathan to show Emily what it's like to be out with a younger man, but they wind up on a stakeout with a wannabe gumshoe (Brett Gelman) impersonating Jonathan. Meanwhile, George goes out on the town with Bernard, but is shocked to learn... (more) that Richard Antrem (Oliver Platt) is a competing restaurateur; and Ray is drawn to an older woman (Olympia Dukakis) after a fight with Leah.

Brett Gelman, David Rasche, Halley Feiffer, John Hodgman, Oliver Platt, Olympia Dukakis