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 that Richard Antrem (Oliver Platt) is a competing restaurateur; and Ray is drawn to an older woman (Olympia Dukakis) after a fight with Leah.