Bloomsbury £18.99

The Finkler Question, By Howard Jacobson

There's a gag in Woody Allen's Annie Hall in which the world's favourite bespectacled neurotic carps on to his squash buddy about a paranoid encounter. "I was having lunch with some guys at NBC," says Woody, "so I said 'Did you eat yet or what?' and Tom Christie said, 'No, Jew?' Not did you? 'Jew eat?' Jew?"

A similar moment of linguistic confusion forms the narrative springboard to Howard Jacobson's The Finkler Question. This charming novel follows many paths of enquiry, not least the present state of Jewish identity in Britain and how it integrates with the Gentile population. Equally important is its exploration of how men share friendship. All of which is played out with Jacobson's exceptionally funny riffs and happy-sad refrains.

A dinner between three long-time friends sets the bittersweet mood for what follows. Julian Treslove is a failed BBC producer and hapless romantic; his old school pal Sam Finkler is a populist and popular Jewish philosopher; and Libor Sevick is an old Czech who once taught them the history of Prague. Sam and Libor have recently become widowers.

Sevick is the steady hand of the trio. Suddenly alone at 90 and living in a cocoon of mourning for his beloved wife, his constancy puts the two younger men's shambling love lives into focus. He's a lovely character, a one-time film journalist who was confidante to Monroe, Dietrich and Garbo, yet remained relentlessly faithful and happy in his little Mittel-European bubble. Finkler, however, rates pomp over domestic reality (his laughable Alain de Botton-style bestsellers include The Existentialist in the Kitchen).

After dinner, Treslove walks back to Regent Street. Lingering outside the oldest violin dealer in the country, he is mugged. By a woman, no less, and one who may, or may not, have called him a Jew in the process. From here on in, everything is under question.

Treslove, whose perspective is the core of the book, is as jealous of his friends' bereavement as he is their success. He is J Alfred Prufrock with an Ophelia complex, longing for a lover to worship who will then majestically expire in his arms. Only he can't keep any of them long enough. If women are a mystery to him, then so is Finkler, who ultimately becomes a byword for his faith: Jewish becomes "Finklerish". Jacobson cunningly crafts sublime pathos from comedy and vice versa. As such, he is the literary equivalent of Tony Hancock, illuminating the conflict, anger, love and dependence created by friendship while wincing at the ignominy and absurdity of the characters' predicament.

Jacobson's prose is a seamless roll of blissfully melancholic interludes. Almost every page has a quotable, memorable line. "Nosebleeding, like grief," states page 49, "is something you do in the privacy of your own home".

The contrary nature of existence was once nailed by Allen in another dining joke. "Two elderly women are at a Catskill Mountains resort and one of them says, 'Boy, the food at this place is really terrible,' and the other one says: 'Yeah I know – and such small portions.'" Now Jacobson has plated up this sentiment in a dish as hearty as Libor's favourite dumplings.

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