We Could Sing a Duet 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.
Gumball! On the run from the police, Jonathan and Ray turn to Howard (Patton Oswalt) for help with trying to find out who framed Jonathan for murder, while George runs interference for them in his own inimitable, marijuana-induced way.
The Blonde in the Woods Jonathan marks the release of his new book but must process some alarming family news before trailing a mysterious woman on another case. Meanwhile, George is reunited with his daughter at his restaurant, where he meets her new boyfriend; and Ray spends a day with his biological son.