The Roof

I find myself on The Roof. Again.

I’d been here before, many a time, in dreams. The roof looks the same and yet it never does; the high roof is in perpetual gloom and nothing can be seen for certain. Things only appear real from the corner of one’s eye, but they vanish upon closer inspection.

Another constant is that The Roof is always surrounded by the silhouettes of other buildings, but even they differ. Sometimes they look archaic, built in times when Gothic was a style of architecture, not fashion; other times they look futuristic, barely even seeming like buildings at all, all rounded curves and sleek designs.

This time though, this time it looked like home.

To me, home is where I grew up in, this little island nation which rose to fame and glory in the mere half a century of its independence. Of course to a boy growing up, I was never aware of this feat, too focused on my games and school, on the pretty lady, Ms Madeline, in the flat a few units down from mine.

Funny, the more I think about it, this Roof looks a lot like the one of my old HDB.

I used to sneak up there, you see. At first, I did in a moment of reckless, defiant youth after an argument with my dad. I used to have rows with him all the time. Even now, the more I think about, I regret those precious moments I’d had with him before his passing. The thing is, I really don’t think I was wrong about what I’d said then; about right and wrong, about what one should and shouldn’t do, about standing by one’s principles.

At 18, I just hadn’t realised how hard living was yet. The toll it could have on your soul… It was never about not knowing the difference between right and wrong, it was about how long one could stand by one’s ideals before realising he has to abandon them to stand at all.

After a while, I escaped to the roof more and more often; you see, I wasn’t the only one in the family to disagree with my dad and the roof would always be quiet, welcoming in its muted glory. I’d just lie there and gaze at the sky, imagining I could see all the different constellations through the light pollution.

I spent a lot of time there, just dreaming of freedom, of growing up.


One night though, one night was different. I went up there for my nightly stretch. I was genuinely shocked when I heard gentle feminine sobbing from up there (you see, there are certain tales of sobbing women who live in the dark that us Singaporeans don’t talk about) but I soon found the source.

It was Ms Madeline.

And she was sitting on the edge, letting her tears fall to the ground far below.

At first, I didn’t know what to say. Could you blame me? This was my childhood crush and now she looked about ready to slip off. Even if I did say something, who’s to say she wouldn’t slip off out of fright?

But she looked like she needed a friend, or at least a listening ear. It might have even been the last time she would have a use for one. So with a slight cough and a shuffle of my feet I asked,

“Uh, Ms Madeline? You alright? It’s me, Henry, from down the hall.”

Shocked she was, but thankfully, her fine behind stayed on the solid roof. We started talking and for once, I surprised myself with my eloquence. At first, it was small talk, little things to keep her mind off crying and sobbing. As we went on though, I started asking her little bits about why she was up here in the first place.

The whole time, I was afraid I’d say something wrong, trigger a sobbing streak that would lead her over the edge, emotionally and literally, but she didn’t. She told me about her life as a teacher; about how she gave everything for her “children”, day in and day out.

Then she told me about how she’d gotten fired.

It was her fault, really, she’d made a mistake. It was during an out of school trip, and her little rascals were being rambunctious as always. While she was busy tending to little Xavier, she hadn’t noticed Caroline wandering off. She hadn’t noticed Caroline speaking to a shady man at one of the exhibits in the museum.

The panic and the outrage that had followed had rubbed her emotionally raw, she’d said. Now, she felt nothing but guilt and pain, perpetual pain, at the thought of what might be happening to poor Caroline. She’d said that life had become a living nightmare, her only escape being the few restless hours of sleep she could catch every night.

That and another thing.

I’d tried to talk her out of it, I really tried my best, but no, she said. She’d made her choice. When she turned to look me in the eye, I’d realised I would be the only witness to her final words.

“Please. Please, just let me wake up from this nightmare.”

And off she went. I’d rushed forward to catch her but all I caught was the faint scent of her perfume; a subtle vanilla scent. I would never forget that earth staggering thud, echoed by an ear splitting shriek.


After that incident, I got into a lot of trouble, becoming a prime suspect for much of the investigation which followed. Thankfully, Ms Madeline had left a note in her apartment.

How kind of her.

I remember that night, I would always remember that night for as long as I’d live. There’s a reason why I always dream of this Roof; it was a symbol of a lesson earned at the cost of a life. A lesson which grew more important as I grew up.

You see as I aged, I realised how similar to my father I really was. All the little things I’d sworn to do differently… I couldn’t. I just wasn’t strong enough. And as my life grew more restrictive around me, as freedom became more like a dream, I’d escape here. To The Roof.

You see, Ms Madeline had left me an important lesson. All one had to do to wake up, to escape from the nightmare, was to fall… and whatever was at the other end would wake you up. Strange, really, she’d never stopped teaching even after getting fired.

As I shuffled up to the edge, I looked over it and I thought I could almost see her broken figure down below. As I stood up there, feeling the thrill, it suddenly occurred to me that I may not be dreaming. That I may even be standing at the edge of the roof of my childhood home, seeing the last view Ms Madeline had.

But no, it couldn’t be a dream, right? Then again, I’d been having those memory gaps… And I’ve been feeling nostalgic since Dad passed.

But as the fear quickened my heart, I realised that it wouldn’t have mattered anyway. My life wasn’t going anywhere; stuck in a dead-end job shifting papers from one stack to another, the most intimate relationship I have was with the Auntie selling bee hoon and no family left to care for… Was there really anything more horrifying than the nightmare my life had become?

A calm, cold resolve filled my soul for the first time since I was a child, since before the incident. Looking down, I made my choice.

I chose to wake up.


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