In 2001, I sat at the Long Bar Lounge of the elegant Raffles Hotel in its colonial splendor of bamboo thatch and creams – where the Singapore Sling was invented in 1915 – watching the lounge act, a Pinoy cover band, when my companion and fellow travel writer, Craig, broke out into giggles.

I asked the usually stroppy New Yorker what was so funny, to which he replied, “I’m marveling at that I’m an American watching a Filipino sing ‘I’m An Englishman in New York” in Singapore.”

It was funny back then, in a time before these unexpected intersections where cultures collided were taken for granted. These days cultural plurality is no longer the mainstay of the wealthy elite  or the nerdy workmen who work the saltmines of the global economy.

An yet it never ceases to amaze me when friends in LA swoon over  Korean burritos from a truck or I find myself bobbing along to French rap. I loved coming upon the often quixotic and quirky mixes of tribes and tribulations mingling, often in far flung places. But coming to Chicago, I found perhaps joining a French- or Korean-language group seemed about as much cultural plurality as I can expect in one of America’s most segregated cities, one that is defined by its neighborhoods – and neighborhoods still largely defined by ethnicity.

That’s probably one of the reasons why I’d felt so displaced at first in America’s third largest city. It’s multi-ethnic by make up: almost equal proportions of Caucasian and Black, then Hispanic, with a dollop of Asian and a sprinklings of other ethnicities for garnish. But then,  it feels more like a cultural neopolitan than a melting pot, where the layers lay stratified without mingling.

When neighborhoods are racially defined, as are social norms, it makes those cultural cross sections I crave hard to find. I loved it that riding the subway or streetcar in Toronto, I’d hear a dozen languages being spoken as I watched neighborhoods morph into each other, having a dialogue with one another until a different set of characteristics took over.

I loved it that the average person would have a cursory knowledge of Asian countries – and certainly never call me Oriental (OK, it only happened once here and she didn’t mean any harm, but my first thought was, “Oriental? What am I? A rug? Should I ask if she considers herself Occidental?) – but would know to ask if I’m Korean, Chinese, or Japanese, or would make the distinction by instinct that the man over there is Ethiopian and not just black.

Chicagoans tend to be cultural purists and they like it that way. Everyone’s just American. Chicago is the most American city I’ve ever been in and is the most American city of its size in the world. It it truly the greatest American city. It’s a vast and ubiquitous blanket of Americana and nostalgia.  And the cultural singularity completely confounds me.

Tolerance isn’t: ” We’re all the same.” Tolerance is: “This is how we’re different and isn’t that neat? How do they do it in your culture?” The variety and infinite mingling of peoples and ideas to create new things is so exciting.  Give me spice, not just meat and potatoes.  And once all the ticks and tocks are acknowledged, an awareness of our universal humanity opens up. I like hot and you like savory but we all need to eat. And it’s from that point of awareness and learning of each other that culture truly becomes alive.

Don’t get me wrong. The trade-off you get for the singular surety and swagger of American culture is delightful: a sense of history, however young, and a sense of solidarity in a behemoth land where, unlike Canada, there are no drawn out debates whether its culture exists. There is a sense of history here and little patience and want of awareness for plurality or elsewhere because here is where it’s happening. Think local, live locally.

I’d thought of myself as a citizen of the world, an easily transplanted weed that grips the earth and thrives wherever the winds of change blow. Not quite as much so as I’d hoped, perhaps.  I’m not sure if I miss Toronto and Hong Kong so much as I miss who I was in my 20s and 30s, at  that particular place and time. And somewhere behind comes the whisper: Give-it-time-and-pressure. No-peeking-till-the-self-is-formed-in-this-new-landscape. The trick is to absorb the facets of this grand land without allowing myself to be hijacked or swallowed whole.

I wonder who this being will be, the Americanized, Chicago-style version of me. A Korean-Canadian in Chicago.