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Medium writing

The Acute Loneliness of the City

“… cities represent our collective optimism about the possibilities out there; the possibilities for work, for self-improvement, and — most importantly — for human connection.”

[Originally for The Coffeelicious on Medium]


… cities represent our collective optimism about the possibilities out there; the possibilities for work, for self-improvement, and — most importantly — for human connection.

Big cities are the future. While our numbers grow larger year by year, and we become more and more interconnected, and while the Earth stays exactly the same, we seem to be moving en masse into the cities of the world—the Hong Kongs, the Manilas, the Jakartas, the Bombays. In literature, cities represent our collective optimism about the possibilities out there; the possibilities for work, for self-improvement, and—most importantly—for human connection. Because when you’re in a place with 5000+ people per square kilometre, you’re bound to meet someone you’ll connect with.

Yet the truth is the lived human experiences of people in cities is a far cry from that almost-naively optimistic idea that genuine human connection is right around the corner. We live in blocks of hundreds of people, but how many of them do we really know? Maybe you wish your neighbour—that sweet old lady who lives next door to you—good morning every evening on your way out to work, and maybe you smile at the occasional stranger you accidentally make eye contact with. But with every friendly neighbour and every stranger you smile at, there are 10 other neighbours you haven’t said a word to since you moved in, and there are 100 other strangers you don’t even acknowledge when you stand next to them on the metro. The truth is that your number of human connections pales in comparison to the number of people you don’t, and will never be able, to know.

Maybe that’s why we feel lonely.


There’s a special loneliness that you only ever feel walking the streets of a big city. It’s a longing you feel when you’re walking under the lanterns of London’s Chinatown, or the trees of New York’s Central Park, or the bright neon lights of Kuala Lumpur’s Bukit Bintang. When you, alone, walk past a 17 year-old boy and his girlfriend (holding hands, smiles plastered across their face), or a 42 year-old woman and her husband (not touching each other, but just belonging in each others’ presence, like the Earth and the Moon—comfortable), or a 24 year-old woman and her new girlfriend (still adorably, awkwardly shy and nervous around each other, blushing at every brush of the hands, the accidental ones and the not-so).

She’s sullen, and tired, but walks with hope in her eyes that she might just bump into someone new around the corner.

It’s a longing I feel deep in my chest, in the part that I always forget exists until it starts to feel empty; just below my throat, in the little nook next to my heart and my lungs. Maybe you feel it somewhere else—in the pit of your stomach, or at the top of your head, like if you’ve had one drink too many. Wherever your longing for human contact rests, we’ve all felt it. Hell, Hozier’s felt it; his video for his song Someone New, starring Natalie Dormer, captures this feeling perfectly.

In it, Natalie Dormer walks around London, stumbling across people she longs to be with and couples she wants to be a part of. She carries the loneliness on her shoulders perfectly; she’s sullen, and tired, but walks with hope in her eyes that she might just bump into someone new (aha) around the corner.

The video ends with her going to sleep on her mattress, her room lit in shades of pink and blue, romantic and cold respectively, alone.


Incities, there are more people than anyone could ever get to know in their limited lifetimes. The Dunbar Number, that is the maximum number of people one person can have in their social group, is 150. For comparison, the population of Toronto, Canada is over 17,400 times that number. We can’t possibly try to get to know everyone; our brains would probably explode. And since we can’t get to know everyone we bump into on the way to dinner, strangers stay strangers. There are unspoken rules about how we’re supposed to act in public; try to make conversation on the London tube, or god forbid you make eye contact, and you’ll be subject to the glariest of glares.

That’s probably why dating apps—Tinder, Grindr, Her and the like—are so popular now. It’s meeting new people without the risk of being creepy or awkward. On Tinder especially, you swipe on strangers’ faces without risk of unreciprocated interest because you only get matched with people with swiped right—an indication of interest—on you too. It’s less daunting than approaching every person in public that you think looks interesting; in real life, the rejection is real. At least you can’t see the left swipes on Tinder.

try to make conversation on the London tube, or god forbid you make eye contact, and you’ll be subject to the glariest of glares.

That’s probably also why so many profiles on these apps—Tinder, Her, and the predominantly hook-up-centric Grindr—have ‘looking for friends :)’ on them.

But after a while, after a couple hundred Tinder swipes, that longing in your chest (or your stomach, or head, or left ear) comes creeping back. Slowly, as your matches build up and as you start realising you don’t get as many replies as you send out messages. So you swipe more—on the train on the way to your lectures, during your lunch break, during your walk home—and your list of matches grows longer and longer.

None of this satisfies. It’s almost like Pokémon; you’re never satisfied with just the thirteen in your current team. You need to add to your roster. You’ve got to catch them all.

[Side note: this really explains the continued popularity of the Pokémon games. C’mon guys. You’ve already released 16 of those things. Give it a rest for a couple of years.]

So you keep walking around, looking to fill that space in your chest (or stomach, or head, or right pinky), eyes darting from stranger to stranger as you walk a crowded street during your lunchtime. And eventually, you meet a stranger’s gaze. Your stomach flips, and though you feel like your insides might just end up becoming your outsides, you keep your composure. You smile at him. He smiles at you. He walks past and, as though nothing happened, you both move on with your lives, your memories of each other fading as quick as your encounter was short.


You keep walking around, and the space in your chest stays as empty as it was yesterday, but feels heavier than ever.

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