David Rakoff spends his life at a considerable remove. A neurotic, homosexual Canadian Jew who has spent almost half his life in New York City working as a journalist – but not a reporter, he is quick to point out – Rakoff defies both assimilation and easy categorization. It is this multi-faceted alienation that both contributes to Rakoff’s considerable skill as a cultural commentator, and gives Fraud, his first collection of essays, its title.

The pieces in this book are collected from sources as disparate as the New York Times Magazine (for which Rakoff is a regular writer), GQ, and Outside magazine. But whether Rakoff is writing about attending a Buddhist retreat led by movie-tough-guy-turned-Tibetan-Lama Steven Seagal, searching in vain for the Loch Ness monster, or visiting Iceland to investigate its legendary fairy folk, Rakoff‘s preferred subject is himself. His simultaneous self-absorption and alienation are the source of much of the book’s humour.

This is not, however, the gently self-effacing personal and observational humour of a writer like Bill Bryson. Rakoff cuts more deeply than that. His alienation and self-doubt are not merely stylistic techniques; rather, there is a core of pain and distance that Rakoff explores with a gentle but incisive hand. Nor is the humour cumulatively funny. Each essay is best read in isolation, allowed its own space.

Readers will certainly laugh, but it is the deeper insights into Rakoff himself that will linger, the images of the author spending Christmas alone at a B&B in New Hampshire, or of his revisiting his cancer treatment (and sperm donation) after a dozen years, that will resonate. Fraud is a perversely funny and deeply, if oddly, affecting read.