New York state of mind

Returning to a city that has changed made me realise that I too have matured with the passage of time

Does the character of a city change over time? Or is it really your perspective that does?

The first time I went to New York was in the summer of 1994.

I had just finished my final exams at a British university and it was still a few weeks yet before my parents would arrive for the graduation ceremony.

It was the best time, really, for any young adult - finally free from the obligations of school, yet blissfully unaware of the obligations of work.

The world was open for us to explore, so a good friend and I decided to go to the Big Apple, the Capital of the World, the City of Dreams.

But having planned a two-week itinerary, my friend pulled out from the trip three days before the flight.

A week later, I sat alone in Tom's Restaurant at the corner of 112th Street and Broadway, looking out the window, humming to myself.

"I am sitting in the morning at the diner on the corner, I am waiting at the counter for the man to pour the coffee," went the Suzanne Vega song, Tom's Diner, whose lyrics I knew by heart.

It was one of the first places I had looked up after I arrived at the grimy Port Authority Bus Terminal, walked 40 blocks and finally got settled in a small Upper East Side hostel with roaches that fell off the ceiling in the middle of the night.

Clutching a well-thumbed Let's Go travel guide and looking out the window, I wondered whether it was this huge, strange city I needed to navigate, or my tangled emotions and identity.

To this young Singaporean, New York was even more of a mess than me. The next 10 days would take me from subversive bookstores to adult movie theatres, from museums that pushed the boundaries of self-expression to parks and neighbourhoods that turned menacing in minutes.

"As I'm listening to the bells of the cathedral, I am thinking of your voice, and of the midnight picnic once upon a time before the rain began…"

All I knew, as I finished up the song that morning in the diner, was that when I walked out the door, I vowed to find myself. And eventually, someday, to also find love.

The next time I visited New York, in 2006, I had found love, but I had also just lost it.

It was a difficult time for me. Just when I had started to feel secure about a five-year relationship I could see stretching into old age, we had unceremoniously broken up.

Devastated, I wanted to leave Singapore behind and start again. So I went on a month-long study trip organised by the United States government for delegates from more than 20 foreign countries to learn about various aspects of trade.

We had criss-crossed the nation, going from Los Angeles to Raleigh to Chicago, before finally arriving for the final leg in New York.

Our mini-United Nations group of economists, public servants and journalists had grown quite close, but once everyone arrived at the Empire City, we went our separate ways.

The most striking thing about New York was how much it had cleaned up under the previous mayor, Rudy Giuliani. There were even signs at traffic intersections prohibiting unnecessary honking.

As I walked past the site of the twin towers of the former World Trade Center - by now just a huge, sad crater in the ground - I felt a palpable sense of loss and renewal about the city.

But it was also the New York I had seen through the lens of all six seasons of the television series Sex And The City (1998 to 2004) - a place where any or all possibilities started with someone interesting or good-looking whom you met on the street, at a party or in a cafe.

"New York City spread herself beneath you, with her bangles and her spangles and her stars," Vega would write a year later, in 2007. "From the 27th floor above the midtown roar, you were dazzled by her beauty and her crime."

Throwing caution to the wind, I went bar-hopping with a friend I had met on the Internet - a Latino comic book artist who part-timed at the giant Toys 'R' Us store in Times Square.

It was a New York that I had, up to then, only read about in books such as American Psycho by Bret Easton Ellis. As the night progressed, we went deeper and deeper into the belly of the beast.

Today, my memory of it is a bit of a blur, but I remember going to bars with dancers who not only danced on poles, but also showered with real water, standing on bar tops. There were bars with patrons all decked out in leather and chains and in cross-dress or no dress at all, in dark basements where unspeakable adventures could be had.

Most of all, I remember wandering through the streets of Greenwich Village, Soho and Chelsea in the dead of night, marvelling at how safe it was compared to the last time I was there.

The New York I knew had indeed changed. Or had I?

That was the question I asked myself when I visited New York again a month ago.

True to form, there is a new song by Vega about the place, from her 2016 album, Lover, Beloved.

"New York is my destination… all of the tales of seduction glittering on the horizon," it goes. "New York is made for grander things, just like me."

In the intervening years, I kept tabs on New York again through the lens of television.

By now the neuroticism of the four women of Sex And The City had been replaced by the neuroticism of the four working millennials on Girls (2012 to present). Out with the tired streets of Manhattan and in with the bohemian neighbourhoods of Brooklyn.

Waiting for the fancy global conference I was attending to start, I made a beeline for Williamsburg - the epicentre of hipsterdom - on a Sunday morning wanting to feel like Hannah Hovarth of Girls, on the hunt for some retro-ironic, upcycled fashion.

I found some at the Kinfolk store, on a street filled with beautiful men in sunglasses and goatees, and women in sunglasses and sun dresses - buying Thai chilli sauce from a store that specialised entirely in hot sauce from all over the world.

Standing there, I contemplated whether I should also buy something for E., the partner I met just after my last trip to New York. We started a new life and have been together ever since.

There was a time when I would have done that, perhaps as physical proof of my devotion or a memento of my trip; a flag to be planted in the house to show that I had been there and done that.

Instead, I took a photo of the shop and posted it on Instagram.

As I wandered the gentrified streets of the city, rife with the orderly energy of working executives and tourists hurrying along barricaded streets with armed policemen keeping watch, I thought to myself that the world has indeed changed.

And in the security of somehow having found what I was looking for all those years ago, in the New York diner that was the subject of a Suzanne Vega song, I think I might have as well.

A version of this article appeared in the print edition of The Sunday Times on June 18, 2017, with the headline 'New York state of mind'. Print Edition | Subscribe