I do not enjoy walking in cities. As a semi-retired travel writer, I often find that people assume I enjoy my job. What could be more pleasurable, after all, than strolling along the Rue Lepic in Paris, or along Via Governo Vecchio in Rome, taking in the sights and panoramas and street cafés with all the gentle aestheticism of an old Baedecker guidebook?

But, when I have done my job well, I have been miserable. Not because cities are bad for the soul, but because they are too punishingly good. I was a travel writer, after all, because I did not like myself when I was at home. I did not want to be my ordinary self, but to be the self I could be in relation to an imagined otherness: to be the sort of person who climbed mountains in the Caucasus, or clambered on ruins in Rome. Existing in new cities was supposed to be a kind of escape from who I was. Instead, it was an eternal, if ever-shifting, mirror of who I could not help but be. I found I was not the panama-hatted adventurers I’d read about imposing my word and will on the world like planting a flagpole. Instead, I was astoundingly vulnerable.

I have walked alone in New York and in Taormina, in Tbilisi and in Yerevan. I have read D. H. Lawrence at a trattoria in Sicily and cried without meaning to and sat huddled against myself on rickety Italian trains as teenage boys talked over me in dialect. I have looked fruitlessly for a nail salon in Trieste and found so many ugly side-streets among the beautiful ones they show you on postcards that I, at last, surrendered and took the bus back to my hotel.

I have walked alone and I have felt lonely, in a profound and soul-wrenching way, not because the city is a rootless place but because it is a teeming one. I start thinking about the last time I was in that city, and who was with me, and whether I loved them, and then I start thinking about the book I read, the last time I was here, and at which café, and how the waiter smiled, and then I start thinking about the people in the books I have read in the cafés in the city, who are also of the city – the rulers and courtiers and writers and courtesans and Caesars who in their own lives walked down these streets and sat at similar cafés and saw similar smiles, and may or may not have been in love, and when you are walking alone in a city there is nothing to interrupt this train of terrible thought but somebody abruptly bumping into you, and this, too, enters into the equation. I feel so terribly lonely, thinking these thoughts, and also so terribly weak, because there is not one of these thoughts that does not seem to abruptly bump into me from outside.

There are so many people, in a city, and so many of them are not me, and so much has happened here, and so much has happened here to me, but so much more has happened here to everybody else. The city challenges us to contend with our comparative smallness. The city reminds us that we are not all that is.

Surrounded by so many others, so much that is not us, who are we? One posture is that of the silent and superior spectator, with his notebook and his spectacles, his quill pen and queer smirk, assessing passersby. Here, the relationship of the self to the other in urban space is one of distancing gazes: pure aesthetic.

The subjective self can be either a dandy – a performer whose purpose is to produce a meaningless effect in his witnesses; Barbey D’Aurevilly, the late romantic novelist and critic, called dandies “miniature gods, who always try to create surprise by remaining impassive.” Or the self might be an observant but disinterested flâneur who revels in fixing all those he observes under his totalizing gaze. The flâneur, as envisioned by Charles Baudelaire, is a “prince” who “everywhere rejoices in the incognito,” whose dominion is at once everywhere and nowhere: he has power over all spaces but obligations to none. “For the passionate spectator,” Baudelaire writes, “it is an immense joy to set up house in the heart of the multitude, amid the ebb and flow of movement, in the midst of the fugitive and the infinite. To be away from home and yet to feel oneself everywhere at home; to see the world, to be at the center of the world, and yet to remain hidden from the world – impartial natures which the tongue can but clumsily define.”

At the core of both these stances is division. There is the Individual – autonomous, powerful, self-creating, even self-divinizing (impartiality is a provenance only of the divine) – and then there is the Crowd: a slow-witted, slow-moving entity, much like the Blob of classic mid-century horror movies, that lacks any distinct or coherent parts. The Individual performs for the crowd, or else the Individual finds a voyeuristic thrill in observing the crowd, but he is not and can never be part of it. The ability to remain disengaged is integral to his sense of self: the Individual exists only insofar as he is separate.

To Charles Taylor, the Catholic philosopher, this sense of separation is an utterly modern phenomenon. Our ancestors of five hundred years ago, Taylor writes in A Secular Age, “lived in an ‘enchanted’ world.” In this enchantment, “forces could cross a porous boundary and shape our lives, psychic and physical. One of the big differences between us and them is that we live with a much firmer sense of the boundary between self and other. We are ‘buffered’ selves. We have changed.”

The buffered self of city-wandering implacably weathers the sensual and spiritual and olfactory onslaught. Traffic lights and taxi-cabs do not affect the dandy and the flâneur. At most, they are titillated, or else exist to titillate others. This titillation is less erotic, in the sense of an outright and vulnerable desire, than it is pornographic: an ironic desire whose consummation lies in arousal for its own sake, and whose true fulfillment is not merely impossible in practice – as are any earthly desires in a sinful world – but in theory, too. Titillation necessitates, inevitably, an anti-climax.

This vision of urbanity – nothing but two sides of a peep show booth, a place in which human interaction is subsumed into erotic commerce – seems to mean that we should all repair to deserts (or caves, or pillars, or the bayou) on the next Greyhound out of town.

But there is another, better, and more Christian way to be in cities – to walk the Champs-Élysées or Ringstrasse or Madison Avenue not simply as detached observers but also fully embodied participants. To walk well in a city is not to be buffered, in Taylor’s sense, but to be porous: to open up the field of one’s own attention to the sheer multiplicity of things that exist, and can exist, in the world. It is not to swell the territories of one’s own self, as the dandy does, but to incarnate into the territories of the world: to pay attention not as a disinterested “prince” but as a full-fledged member of the crowd, one human being among many.

The old man with too many dogs on his leash in Trieste’s Piazza dell’Unita, the jocular street preacher on the Las Vegas Strip, the elderly woman wearing furs at the Carlyle Hotel – these characters we meet in the city are at once exactly as human as we are and profoundly, even joyously, other than what we are. Far from a shapeless mass, they reveal the complexity of God’s creation – of each, irreducible, different, eccentric, exasperating, inhabitant. “Another hundred people just got off the train,” Stephen Sondheim writes in Company, “and came up through the ground/ While another hundred people just got off of the bus/ and are looking around.”

At its best, the experience of being in a city is the experience of not just present otherness but the greater democracy of the dead. From Roman ruins to Habsburg palaces to decaying art nouveau brasseries to boarded-up Brooklyn galleries, the physical landscape of cities reminds us of both human vision but human frailty. At Miramare Castle just north of Trieste, the Habsburg Emperor Maximilian I of Mexico – who later was deposed and killed and whose wife went mad – slept not in a bedroom befitting an imperial ruler but a tiny, enclosed room modeled upon the cabin of a ship: the only place the man ever felt comfortable. To walk the Miramare halls isn’t merely to experience the grandeur of a vanished age, but come face to face with the material remnants of a very human person: each hand-carved pineapple a testament to the particularity of a man whose fears and neuroses and longings shaped a corner of the polyhedron of history.

Every monument, every palace, every attempt (inevitably a little bit in vain) to quantify and control space is a record not merely of kings and governments but of very real, very particular, and very human desires: to be remembered, to make sense of senseless space, to interpret and tame the wilderness.

When we walk among the heads and ruins of Agrigento we aren’t just appreciating the fact of classical engineering. Rather, we appreciate the Ozymandias beauty of noble failures: physical manifestations of that which we share as surely as death itself, which is our fear of irrelevancy. Something, these monuments suggest, beside remains. People made these buildings. People designed them. People wanted to say something with them. People wanted other people to remember them. Or else they just wanted to sleep comfortably, and dream well.

This is an incarnational flânerie, one that demands that we enter the world, that we live in the world, in the messy and smelly and strange and overwhelming world full of people bumping into us, and ideas crashing through our reveries. We do not have control over this city. We are contingent selves, communal selves. We bump into strangers and pass by, or do not pass by, the injured on the side of the road.

When we walk cities in such a way, we are not subjecting ourselves to temptations of Babylon but rather undergoing the purifying trials of pilgrimage to Jerusalem: learning to unmake ourselves so that we can be alongside others. We are no longer peep-show spectators, but rather delighted fellow-brethren. We “find each other in the crowded streets and the guarded parks / By the rusty fountains and the dusty trees with the battered barks,” per Sondheim, and “walk together past the postered walls with the crude remarks.” We are strangers, insofar as we are alien to other, but in this “city of strangers” we find the bonds of attention, to one another’s strangeness, that can foster love.

I have learned to get better at walking in cities, lately. It might be age. It might, too, be a reaffirmation of faith. I am no longer as afraid as I once was of the kind of loneliness that comes from encountering so many hundreds of other people.

Sometimes, now, when I am out late in New York, when I am a little drunk but not very drunk, and when the trains misbehave, I even decide that I will walk home myself. I walk past all the people and all the buildings full of people, and made by people, and made for people, past the Times Square superheroes and the tourists vomiting on trains, past children and early-rising builders and the liminal denizens of twenty-four hour diners, and I keep walking however long it takes for me to get home. I do not look at my phone. I take it all in.