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 impersonating Jonathan. Meanwhile, George goes out on the town with Bernard, but is shocked to learn that Richard Antrem is a competing restaurateur; and Ray is drawn to an older woman after a fight with Leah.

Cast: Jason Schwartzman, Zach Galifianakis, Ted Danson, Heather Burns, John Hodgman, David Rasche, Halley Feiffer, Olympia Dukakis, Oliver Platt, Brett Gelman, Paula Leggett Chase, Angela Cristantello, Barry Godin, Chris Miskiewicz, Matthew J. McCarthy