What is it about the Big Apple that obsesses us?

Living in New York is an almost constant exercise in overcoming your own cultural expectations. There is surely no place on earth more saturated by film, literature, and song than the Big Apple, and vast swathes of our psychogeography are dominated by the lower chunk of Manhattan.

Walk along Bleecker Street and you’re in a Simon & Garfunkel song. Head up to Lexington and suddenly you’re in the Velvet Underground, waiting for your man. For me, any trip to the Plaza hotel is a journey into the privileged desolation of The Great Gatsby, but also the heartwarming absurdity of Home Alone 2. I cannot ever hear the words Clinton Street without thinking of Famous Blue Raincoat by Leonard Cohen: “New York is cold, but I like where I’m living, there’s music on Clinton Street all through the evening”.

It is a city of visions and reflections, where your actual life and your cultural memories often intersect. But if you are to make the place your home, as I have for the last two years, then at some point you have to supersede the fables and turn your life into a reality.

"An Englishman in New York isn’t just a person, he’s a literary trope. Sting even wrote a song about it..."

New York was the obvious choice. The job was there. I speak the language. But there was another reason too: it is the city of childhood aspiration. If you grew up in a western country any time in the past century or so, if you were ambitious and literate and adventurous, then a youthful sojourn in New York almost certainly represents some sort of pinnacle or life goal.

But you take a lot of baggage with you. A lot of expectations. Some of these are the cinematic ones I’ve already described, which can be quite oppressive. If you don’t find yourself enveloped by a loving and eccentric West Village-dwelling clique within six months, then you feel like a failure. If you choose to stay at home on a Saturday night, to vegetate in front of Hulu with your girlfriend, there’s an accompanying guilt that you wouldn’t feel elsewhere, as though the Bright Lights Big City life is passing you by.

But there’s another layer to that guilt too. You’re an Englishman in New York. What better thing is there to to be? A young bachelor from Blighty in the finest city on earth. Long, louche, chaotic nights of drinking and carousing with strangers from bars surely await. You merely need to open your mouth, let the Received Pronunciation flow out and the city is yours.

An Englishman in New York isn’t just a person, he’s a literary trope. Sting even wrote a song about it. Manners maketh man and you’ll be the hero of the day, or something like that. Think of Peter Fallows, the cynical, sozzled British hack in Tom Wolfe’s Bonfire of the Vanities.

"The accent thing is, to be honest, a bit overrated..."

Or indeed, going back further, PG Wodehouse’s Bertie Wooster, who in his own hapless way conquered the New York of the jazz age from his apartment in Stuyvesant Tower. More recently, Patrick Melrose’s epic quaalude and cocaine bender from Edward St Aubyn’s books, just made into a TV series, sets the standard for a debauched weekend in the Big Apple.

As a journalist, this sometimes intimidating sense of being on a well-trodden and glittering path is amplified by the exploits and achievements of hacks gone by, which haunt the industry. Geordie Greig, pointed editor of the Daily Mail, used to do my job at The Sunday Times. His editor at the paper was Andrew Neil, who recalled visiting Greig during his tenure and going for lunch with Henry Kissinger. I recently took my editor for a pint.

The accent thing is, to be honest, a bit overrated. There are thousands of English men scurrying about New York. Nowadays, most of them sound more like Tim from The Office than Prince Charles, but either way it’s not the linguistic black Amex card that everyone thinks it is. What the accent occasionally does is open conversational doors.

I don’t consider myself emotionally stunted. I love to watch romcoms. I go to a therapist sometimes to blither on about low self-esteem and depression. But American girls can be a stretch.

"I drink a middling amount by English standards, but in New York I drink more than everyone else..."

One ex-girlfriend wrote about me in a recent New York Times column: “Dating a Brit, which I did for a while, has many downsides. You gain a minimum of ten pounds from the alcohol intake. You become needy, given that they have the emotional bandwidth of a dry scone.”

I actually think I’m closer emotionally to a Blueberry muffin, but she was right about the drinking.

I drink a middling amount by English standards: most days in moderation, some days not in moderation. But in New York I drink more than everyone else. When I order wine in a restaurant, I have to insist, firmly, that I want a bottle and not just a glass. When I partake at lunch, people shake their heads in disgust. This is still a puritan country.

In truth though, I’ve mostly found the Englishman in New York myth to be just that: a myth. What’s really changed today is the global monoculture. Where I live, in gentrified west Brooklyn, my Englishness is moderated by how closely aligned my tastes and experiences are with my neighbours. Until I open my mouth to express my ignorance of snow cones or Law & Order, I’m really just another bearded millennial stocking up on hummus and pita bread at the supermarket.

After two years living in New York, I think I’ve shed most of the cultural baggage. I’ve all but forgotten the fact I sound a bit weird to most people and am not too proud to say soccer, sidewalk, subway and cilantro, for the purposes of avoiding confusion. I can walk down Bleecker Street free of Paul Simon and along Lexington without Lou Reed.

"After two years living in New York, I think I’ve shed most of the cultural baggage..."

What has liberated me from all the cinematic expectations is an important lesson, not dissimilar to the moment when a young man finally accepts he really will never play for Manchester United. New York is still the most exciting city I’ve ever visited.

My life is often thrilling and I will undoubtedly look back on my time here with misty-eyed longing. It will probably be the best thing I ever do. But no one will ever make a movie about it.

Read the full story in the Sept/Oct issue of Gentleman’s Journal. Subscribe here…

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