22 SUPER-Creepy Real-Life Stories From Working The Night Shift


“I used to work for a sub shop as a delivery driver. Weirdest thing was the Montana Cowboy. I am located in Milwaukee, WI, so we have a diverse crowd of homeless. One night around 1 AM a cowboy-lookin’ dude walks into the shop. He seems just off on something. Can’t form any sentences whatsoever. All I could get out of him was his name, Ben. Ben seemed like he was very drunk (smelled like it, too) and had something else in his system. He kept kind of saying the same gurgled mess over and over. No idea what he was saying. Me and the manager I was working with are pretty chill guys, so we offered him some soup and a sandwich for free. He was so happy and thankful (I think). While he’s eating, I went out on a delivery and stopped the car at an apartment. As I’m walking up, a cowboy walks out. Not the same cowboy but a different one. I said hello or whatever, but he responded with the gurgled mess the guy in the shop said to me. Like same cadence and tone, everything. Even kinda looked like him. I thought that was weird. So I got back to the shop and cowboy is still there. He’s eating and saying nonsense. My manager found out he was from Montana. So I go on another delivery. Walk up to the apartment building, but wait a fuckin’ second, there’s a ma fucker with a ma fuckin’ cowboy hat sitting on the stoop and asks me for a dollar. I told him all the cash I have is for my work. He said a gurgled mess like the last two guys and I left. Now here’s a fuckin’ kicker. I go back to the shop and Ben is gone. So I go on my last delivery around 3 AM and pull up to a house. It’s lit up inside and I can see people are moving around with the shadows on the window. I knock on the door…who answers?? FUCKIN BEN! And who’s in the fuckin house with him?? THE OTHER TWO FUCKING COWBOYS! Ben says, ‘sup’ hands me a $100 bill and slams the door. I was dumbfounded.”



“I used to work third shift security in a neighborhood near a university. We often encountered some weird stuff, but mostly we just dealt with drunk college bros and the like.

One night it’s nearly 4 AM so we’re ending our shift and heading in when this old homeless-looking man stops me and asks me to call an ambulance for him. I ask what’s wrong and he’s telling me he’s having heart palpitations and suicidal ideation. I flag down a coworker who informs our boss and calls for the ambulance.

I sit down next to the guy as he’s laying on the sidewalk and let him talk to me. At first he’s saying what you’d expect from someone who wants to commit suicide then it gets dark as hell. He starts telling me about a woman he stabbed because he asked her for $20 but she only gave him a few bucks so he murdered her.

OK, pretty creepy, but then it gets worse. He just starts going on about how he’s raped people and committed arson and other horrifying stuff and I’m sitting almost alone with him while my coworker is several buildings down on the phone with dispatch. He starts telling me about how his mother used to have sex with her father and brother and that he saw that? And about how he’s a crackhead.

When the ambulance arrived he started cussing and yelling but at least I was free to go at that point. I understand it was probably at least partially the ramblings of a mentally ill crackhead but it was still unnerving. It’s not every day a stranger confesses to you about murder and rapes he’s committed.

Also, I’m a young woman, so I would occasionally get the super fucking creepy guys who would try to corner me on dark roads or follow me around. So that would get pretty terrifying.”


Thought Catalog

Thought Catalog is the online destination for culture, a place for content without the clutter. Coverage spans the ...

More From Thought Catalog