Smiling Man

The Smiling Man is a scary creepypasta story about a young man who goes walking late at night and comes across a very disturbing individual on the road.

This happened five years ago when I lived in an apartment in the city. I’ve always been a night person, so after my roommate went to sleep, I would often go for long walks to pass the time. Walking alone at night, I never once had a reason to feel afraid, but one evening, all of that changed…

It was a Wednesday night, somewhere between one and two in the morning, and I was walking by a park that was quite a distance from my apartment. It was a quiet night and there was very little traffic. The streets were completely empty.

I turned down a short side street, on my way back to my apartment. That was when I first noticed him. At the far end of the street, I saw the silhouette of a man. He was dancing.

It was a strange dance, similar to a waltz, but he finished each “box” with an odd forward stride. I guess you could say he was dance-walking and he was headed straight for me.

Deciding he was probably just a drunk, I kept as close as I could to the edge of the sidewalk to give him enough room to pass me by. The closer he got, the more I realized how gracefully he was moving. He was very tall and lanky and wore an old, threadbare suit. He danced closer and closer still, until I could make out his face.

His head was tilted back slightly and his eyes were wide open, looking up at the sky. His mouth was twisted into a painfully wide smile, almost like a cartoon. Between the wild eyes and the grotesque smile, he gave me the creeps and I decided to cross the street before he came any closer.

I took my eyes off him to cross the empty street. When I reached the other side, I glanced back and stopped dead in my tracks. He had stopped dancing and was standing with one foot in the street, perfectly parallel to me. He was facing me but still looking skyward. The grotesque smile was still wide on his lips.

I was completely and utterly unnerved by this. I started walking again, nervously keeping an eye on the man. He didn’t move. Once I had put about half a block between us, I turned away from him for a moment. The street and sidewalk ahead of me were completely empty. Still unnerved, I looked back to where he had been standing to find him gone.

For a brief moment, I felt relieved… until I noticed him. He had crossed the street, and was now slightly crouched down. I couldn’t tell for sure due to the distance and the shadows, but I was certain he was facing me. I had looked away from him for no more than 10 seconds, so it was clear that he had moved fast.

I was so shocked that I stood there for some time, staring at him. And then he started moving toward me again. He took giant, exaggerated tip toed steps, as if he were a cartoon character sneaking up on someone. Except he was moving very, very quickly.

I’d like to say at this point I ran away or pulled out my pepper spray or my cellphone or anything at all, but I didn’t. I just stood there, completely frozen as the smiling man crept toward me.

And then he stopped again, about a car length away from me. Still smiling his smile, still looking to the sky.

When I finally found my voice, I blurted out the first thing that came to mind. What I meant to ask was, “What the hell do you want?!” in an angry, commanding tone. What came out was a whimper, “What the hell…?”

Regardless of whether or not humans can smell fear, they can certainly hear it. I heard it in my own voice, and that only made me more afraid. But he didn’t react to it at all. He just stood there, smiling.

Then, after what felt like forever, he turned around, very slowly, and started dance-walking away. Just like that. Not wanting to turn my back to him again, I just watched him go, until he was far enough away to almost be out of sight. And then I realized something. He wasn’t moving away anymore, nor was he dancing. I watched in horror as the distant shape of him grew larger and larger. He was coming back my way. And this time he was running.

I started running too.

I ran until I was off of the side road and back onto a better lit road with sparse traffic. Looking behind me then, he was nowhere to be found. The rest of the way home, I kept glancing over my shoulder, always expecting to see him leering at me with his creepy smile, but he was never there.

After that night, but I never went out for another walk. There was something about his face that has always haunted me. He didn’t look drunk, he looked completely and utterly insane… and that is a very, very scary thing to see.