I am in the United Arab Emirates, commentating on England’s Test series against Pakistan. Not long after the first day’s play in Dubai, I witnessed a revealing scene. A few dozen England fans – a good portion of the crowd – had to wait 90 minutes outside the ground for a taxi. Some people were at street level and the system short-circuited.

Cities are usually set up to supply the needs of crowds. Dubai is predicated on the absence of pedestrians. No wonder it’s a celebrity hot spot. Amenities and services exist in a vacuum. If you find other people irritating, Dubai is very attractive.

Why didn’t the cricket fans walk? The hotel was 20 miles away and the temperature was 36°C. People do not walk anywhere here. They leave their air-conditioned homes, enter air-conditioned cars and arrive at air-conditioned malls or restaurants – then reverse the process. Desire is stripped back. What do I want and where can I get it? It is said that you can buy anything in Dubai, but only if you know exactly what you want.

Literalism reigns. Dubai is broken up into purpose-built ghettos. There is an Academic City, a Golf City, an Internet City, a Motor City, a Studio City, a “celebrity city” (the Palm), a Design District. Interaction between these “cities” is limited by swaths of desert. Geographically, they are miles apart. In feel, they are even more remote.

On the way to the cricket ground in Sports City, we drove through Media City. One building was branded: “Dubai Creative Clusters Authority”. Even creativity must be consciously and deliberately “clustered”. In most cities, the recipe for creative clustering is buying coffee and flirtatiousness. In Dubai, in place of the humble queue, there is an authority and a car park.

Literalism is overlaid with gigantism. Everything must be the world’s biggest. Dubai has the world’s highest building (the Burj Khalifa), the biggest mall (the Dubai Mall), the biggest Ferris wheel, the unlikeliest ski resort (22,500 metres of snow slopes in the desert), the biggest floating water park. And what are they like? Dubai Mall is like a large mall, only larger. The Burj Khalifa is like a very tall building but taller. If you have an imagination, there is little to see.

If you are lucky – and not one of the working poor who sustain the rich’s standard of living – there is huge material comfort. Hotel rooms are enormous, more spacious than apartments in normal cities. I have zoomed along seven-lane motorways in cars designed to seat seven ample bottoms. Restaurant chairs resemble cinema seats.

You can look after your body easily. Man-made beaches are sprinkled liberally around Dubai (one of the triad of ever-present fake “B”s in the region – Breitlings, beaches and breasts) and gym culture is well developed. Yet I felt oddly claustrophobic and caged, despite swimming and trips to the gym. Eventually I realised what was missing: I had scarcely walked anywhere, at least not outside. I was ungrounded.

I came to Dubai via New York, an accidental counterpoint. I was attending a party to mark the 75th birthday of the philosophy professor William James Earle. I met Bill in 1998 when I was 21 and new to New York. A mutual friend had told me that there was no better way to come to understand and love the city than by getting to know Bill and his circle of friends in St Mark’s Place in the East Village. So it proved.

Bill’s fourth-floor “walk-up” apartment, across the street from W H Auden’s old flat, is a narrow rectangle centred around four weathered Le Corbusier chairs. The walls are covered with books on almost every subject (sport is almost entirely ignored). Aesthetically, it is unmistakably modernist but without the usual coldness. The layout of the apartment – at 850 square feet, it is about the same size as an Abu Dhabi hotel room – conspires towards conversation and reading. There are always more things (usually books) than space. One lesson of Iris Murdoch’s novels, as Bill would put it, is that untidy lives are more open and interesting.

When I first visited his apartment, it all seemed exotically bohemian. An ­Oscar, a present from the choreographer Jerome Robbins (who had won it for West Side Story), was tucked into a recess in the wall. Scarcely a day went by without a visit from a beautiful ballet dancer. Eventually, I realised that it was just how they lived – a lifestyle founded on a commitment to the arts, strengthened by unlikely friendships, nourished by surprising connections between people and ideas. Though the effect was an enviably interesting lifestyle – a kind of downtown salon – nothing was just for show. It was a rational kind of bohemia. Why live a less interesting, narrower life?

What a contrast in urban experiences. In St Mark’s Place, a tiny space supports literature, friendship and surprise. In Dubai, massive expanses are filled with literal utilities and dead ends. Even the skyscrapers serve different needs. Manhattan’s high-rises, squeezed into an island of fixed dimensions, owe something to necessity (as well as one-upmanship). In Dubai, where apartments are often uninhabited and the population density is low, there is no need for skyscrapers at all – but they give the city the perception of urban grandeur and perception is everything.

Cities at their best curate serendipity, just like a bookshop (where you might buy the adjacent book) or a newspaper (which might draw your eye to a surprising subject). You go looking for one thing and find something else. There were few places less likely for a young English professional cricketer to call home than the East Village in New York. That taught me the importance of surprise.

In Dubai, surrounded by world records, I have not felt a trace of wonder. Its trademark is inverse serendipity: you get exactly what you came for.