After celebrating the release of his new book The Blonde in the Woods, Jonathan learns some distressing familial news. George reunites with his daughter Emily and meets her new boyfriend. Ray spends time with his biological son Spencer. Meanwhile, Jonathan's latest case leaves him in a precarious position.
While showing Emily a "youthful" time, Jonathan discovers a classified ad for a detective impersonating himself. On a night out with Bernard, George learns that Richard Antrem has opened a restaurant aimed at hurting George's restaurant. Ray, in hot water with Leah, finds himself drawn to a lonely woman named Belinda (Olympia Dukakis).
Writer turned private-eye Jonathan Ames was last spotted duking it out in a dean's office, (almost) saving Super Ray from a stalker, and endorsing George's decision to resign from his glossy magazine gig. This season Jonathan will come face-to-face with "furries", hang with Dick Cavett, and go on the ultimate oedipal investigation!
A Brooklyn-based writer whose long-anticipated (by his editor) second novel was rejected, Jonathan must make ends meet in the tradition of countless novelists before him: teaching and freelance writing. With a deep fondness for white wine and marijuana, Jonathan is a questing, sensitive soul who often turns to his best friend Ray or his mentor and sometimes-boss George Christopher for solace and advice. In addition to being a struggling writer, he has a yearning to be heroic and have adventures - and he wants to help people - so he leads a double life as an unlicensed private detective.
The editor of 'Edition NY' magazine, and Jonathan's sometimes employer, George has been a tastemaker and man about town for decades. He's had three marriages and countless lovers. His penthouse bachelor pad and high-rise office may be peppered with souvenirs of his success, but George has become somewhat inured to a life that garnered him his own Chuck Close-esque portrait. George has become friend and mentor to Jonathan, perhaps as a way to vicariously reclaim his youth and to escape boredom. Also, Jonathan has access to marijuana, which pleases George immensely.
A talented but not-yet-financially-successful cartoonist, Ray is Jonathan's best friend. He's something of a tormented curmudgeon and he isn't afraid to challenge Jonathan on an ill-advised decision, but when Jonathan is in trouble, Ray's there - in whatever capacity necessary. He's Sancho Panza to Jonathan's Don Quixote.