by JULIET WATERS

In one way, it’s easy to see why David Rakoff is GQ’s writer-at-large. He’s very funny and highly intelligent. In other ways, it’s a weird fit. He’s gay, which can be an obvious drawback when he’s assigned to cover a Playboy shoot in Belize, or flies to Myrtle Beach on Hooters Air. Also, he’s a self-described Art Fag, whose dream job is more likely writer-at-large at Martha Stewart’s Living. Of course he would never get that job, if only because of paragaphs like this:

“I am anti-fun. Not as in anti-violence, but as in anti-matter. I am not so much against fun—although I suppose I kind of am—as I am the direct opposite of fun. I suck the fun out of a room. Or perhaps I’m just a different kind of fun; the kind that leaves one bereft of hope; the kind of fun that ends in tears.”

This insight is delivered at the end of a “Midnight Madness” scavenger hunt in East Manhattan. Not that there’s anything really wrong with roving gangs of geeky sleuths, but I suspect that eight hours of solving puzzles and bickering over directions wouldn’t leave anyone too gregarious at 4 a.m. The glue that holds this collection of wildly disparate subjects together is Rakoff’s status as a hardcore New York City loner. He’s like Fran Leibowitz, the curmudgeonly essayist who lives in one of the most populated cities in the world, because, paradoxically, it’s the place where people who don’t love people (or at least all people) are the happiest if not the luckiest. At heart, Rakoff is the kind of loner that few people have the guts to be. It’s what makes him honest, acidic, funny and sometimes mean yet weirdly soulful.

Oh it’s no surprise that he left Toronto as soon as he was legally old enough to do so. But it is a surprise that he would want to become an American. Loners are not known for lining up to take the pledge of allegiance, or for statements like, “George W. Bush made me want to be an American,” however obviously ironic.

“I have lived in the United States, first as a student then as a resident alien, under numerous other administrations, including what I once thought of as the nadir of all time: the Cajun-scented, plague-ravaged Reagan ’80s in New York,” he says. “Horrible, black years of red fish and blue drinks. A time when greed was magically transformed from vice to virtue.”

His assertion that he became an American because, “I no longer felt safe being here as just a lawful permanent resident,” as though he was likely to be deported to Syria, seems a little disingenuous. A bone, perhaps, thrown to the citizens of his native country, to which I suspect he was far more afraid of being deported.

It’s not that he’s lost all sense of connection to Canada. “Once I reach my decision, I don’t make my intentions widely known,” he explains. “I tell almost no one, especially no one in Canada. You can only know this if you grew up in a country directly adjacent to a globally dominating, culturally obliterating economic behemoth, but becoming an American feels like some kind of defeat. Another one bites the dust.”

The truth is probably a simple paradox. David Rakoff was, in a certain way, forced to become an American because it was the only way he could continue calling the country he lives in a “globally dominating, culturally obliterating economic behemoth.”

Anti-American American and loner that he is, one still wouldn’t call Rakoff cynical or even hostile. It’s impossible to believe anyone this in love with Martha Stewart could be. As the Playboy shoot shows—which will work best for anyone who’s ever had the experience of feeling truly and completely alienated—there’s always a joy he takes in observing people, even if he doesn’t always connect.

Don’t Get Too Comfortable by David Rakoff, Doubleday, pb, 224pp, $33.95