A Personal Encounter by a Former Chess Kid, Now Wandering Through Aliwal

The Invitation I Didn’t Expect

I didn’t even know Singapore had street chess.

A few months after moving here. Somewhere between adjusting to MRT life and chasing client deadlines, a friend casually said to me, “You should go play chess here.”

Huh? Chess? In Singapore?

My fingers moved fast. Instagram. Search bar. Aliwal Chess Club. And just like that, my nerdy little heart fluttered.

This City Moves Fast –– So You Walk

They actually have it here. Open air. Real sets. Real people. And it’s free?

I didn’t know what made me more excited. The idea of playing again with actual humans (not just my sleepy phone app games at midnight), or the fact that this whole underground-ish scene existed in the midst of this hyper-efficient, work-till-you-drop city. Because let’s be real: Singapore life is fast. You walk fast. You eat fast. You even breathe fast. Some days I miss the ease of just jumping in a car, going wherever. Here? You’re either walking, sweating, or thinking twice before opening your Grab app. A 2km ride could cost SGD 10. I’m not kidding. So… you walk.

And that’s what I did that day. Walked. Just finished work, late Sunday, brain fogged, hands holding an empty lemon tea packet. I was just trying to find a bin.

A Giant Gameboard and a Universe That Whispered

And then I saw it.

A giant chessboard. Life-sized pieces moving like something out of Alice in Wonderland – but the Singapore version. Each piece stood almost up to the waist, carved in smooth, solid black and white stone-like material, heavy enough to require both hands to move with care. The board itself was built into the floor, tiled in sharp contrast, gleaming slightly under the late afternoon sun. People were actually playing, lifting these massive pieces as if they were part of some sacred ritual. There was nothing gimmicky about it – it was grand, grounded, real. Players giggling, shouting. No shoes. Just energy. Fun.

And behind that? A long table. No, two. Over 15 chess sets lined up, digital clocks ticking, heads bowed in battle mode. I froze. Not out of fear. Out of… awe. Like, how is this real? How did I not know? How did I just walk into something that felt like it was calling me?

It felt like a wink from the universe. “You,” it whispered. “This… this is your place.”

Memory, Muscle, and a Puzzle in My Hand

I stood there, still holding my cup, eyes darting around like a kid in a toy shop. I must’ve looked lost, because one of the ushers came up to me with the warmest smile and said, “Would you like to solve a chess puzzle?”

I laughed. “Oh my God… it’s been so long.” I used to play, way back. 1994. Almost made it to nationals, but reserved bench didn’t count. Life happened. Chess stayed buried. Until now. They handed me a piece of paper. I stared at it. And then something happened. Not muscle memory. Not strategy. Just... something old waking up inside. I solved it. We both smiled. I felt ten years younger.

Everyone Plays Here

Balanced mix of races. Locals. Expats. Students. Parents. All just… playing. I looked around and saw something I rarely get to witness so clearly. Chinese, Malays, Indians – the three major races in Singapore. All present in what felt like an almost equal number. No one dominating. No one left out. And that, to me, was beautiful.

Here, it wasn’t about who you were. It was just about the next move.

People were laughing, exchanging tips about opening theory, middle game tactics, endgame traps. Terms that felt dearly foreign to me now. I mean, come on, I’m in my 40s, have delivered babies, and the last time I took chess seriously was almost 30 years ago! My brain blanked at “pinned” and “hook.” But the vibe? Still so welcoming.

One Language, Many Cultures

Another thing I admire deeply about Singapore is this: the kids – regardless of race, all speak in one common language: English. Sure, there are pros and cons to this system, but it minimizes racial barriers. It creates a kind of baseline camaraderie, even in a country that prides itself on its diversity. And of course, being Singapore – the hub of Asia – you’ll always find foreigners like me blending in. I even noticed a few other Southeast Asians, maybe from the Philippines, Vietnam, or Thailand. And yes, the occasional Caucasian, probably just stumbled over from the street fair or stopped by after hunting down the famous taco joint nearby. But no matter where they came from, they sat. And played. As if this was the most natural thing in the world.

That warmth, the spontaneous, communal spirit – it’s not what most people imagine when they think of Singapore’s “workaholic” image. But it’s there. Underneath the speed and the steel, this city plays too.

A New Chapter, Maybe?

One of the ladies from a chess academy came over and said they were looking for coaches—across Singapore schools. She said they even train the trainers. And they pay you.

At first, I said, “Oh no, I’m not a pro – it’s been like 30 years. I don’t even have a FIDE rating. I just represented the school, that’s all.” But then I laughed and added, “Count me in anyway. Even if it’s free, I’d do it.” There’s something about teaching chess to kids that feels deeply fulfilling. Maybe it’s because I have a daughter too. I tried teaching her chess when she was four. Of course, she mostly just played around—but I remember clearly how she could arrange the pieces properly, knew where the white queen and knight belonged, and even remembered their names. But since I had to leave her when she was five to come to Singapore... she stopped playing.

Then the young girl, probably in her early 20s, smiled and said, “Oh no, we pay our coaches.”

And I was like – what’s this?

Something lit up in me. Not because of the money. But because for once, it felt like I could pass something real on. Not violin this time. Chess. A language I haven’t spoken in years, but never forgot.

The Move That Found Me

I came to Singapore to work, to build, to heal. But that day, I found a little piece of me again.

So if you ever hear the tick of a chess clock echoing through Aliwal Street – stop. Don’t just walk past it. It might just be your move.