Bored to Death - Season 3 Episode 4
We Could Sing a Duet

George urges Jonathan to show Emily what its 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.