What is your weirdest homeless encounter?

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I once was approached by a homeless lady that was selling "expensive rings" for just 2 dollars a pop. The "rings" in question? They were gas fittings.
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I once was approached by a homeless lady that was selling "expensive rings" for just 2 dollars a pop. The "rings" in question? They were gas fittings.
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This is why I made this!I laughed out loud, ty

You know she was just going to Home Depot/Lowes/Ect and just pocketing fistfuls of these things. During a schizo episode it probably seemed like a flawless plan
 
Given the area I live in, you'd think I'd have more stories like this - but the scariest one happened a couple of years ago. I had just left a friend's party and, being a broky, I had to wait around for the subway to open at 6. It was dark and cold, close to winter. I got to the door, lit a cigarette, and just kind of zoned out, waiting for the station guy to show up and unlock the doors. That’s when I started hearing this rhythmic bumping sound.

I looked around and across the street I saw a woman, barefoot and completely disheveled, gently (or whatever you'd call it) slamming her head against the window of our national retailer. Over and over again. She’d pause, then go right back to it.

I just stood there smoking, watching her for a solid 20 or 30 minutes. She never acknowledged me just kept going. When the subway finally opened, I went inside without ever seeing her face clearly.

But I still think about it sometimes. Whatever it looked like by the end of that it couldn’t have been good. Worse is that she probably could see me in the reflection of the glass, and it's never good to cross eyes with these kinds of people.
 
I once was approached by a homeless lady that was selling "expensive rings" for just 2 dollars a pop. The "rings" in question? They were gas fittings.
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Methheads sure are creative, I'll give them that.

On the topic of enterprising homeless methheads, as a teenager, I once had one randomly pop out of the bushes (I think he had an encampment there?) while I was riding my horse on a trail & he generously offered to rustle me any horse I want for for 150 bucks. Note: I'm from semi-rural Oklahoma - stealing someone's animals is basically a suicide attempt, on account of nearly all property owners here being armed to their teeth/having motion sensors cameras & electric fences due to coyotes. Also, aside from being a felony, stealing someone's horse is generally a dick move - horses are smart they recognize & miss their people. Anyway, when I turned down this offer, Methhead proceeded to peddle his wild hog catching services - 50 bucks per hog. TLDR I galloped away (he spooked my horse who froze or I would have gotten out of there much sooner).

Months later I saw his mugshot in an issue of Jailbirds, I think he was caught trying to steal a Honda Civic from a Del Taco parking lot.
 
I was walking in the city one day and a homeless guy approached me. I pretended I only spoke German and waved him off. Later that night I was out with a friend and the same homeless guy approached us and started to tell my friend his life story. So I told my friend to fuck off and let's go since we were headed to a club.
 
Old, black inner city crackhead who would do absolutely incredible backflips for $5 or a beer/cooler. Referred to himself as a war veteran with the rank of "lieutenant sergeant" or some shit. Of what branch? Which war? Depends on the day you asked him. He was entertaining, and I hope his inevitable overdose and death will be/was of the relaxed and sleepy variety.
 
Nothing too crazy. I remember one time I saw a homeless person sitting outside of a pizza place asking customers to buy food for him as if they were his waiters.
 
I was once drinking in this little college town and was sitting outside the bar by a burrito truck. This absolutely sloshed college girl walked up to me and forced me to take a burrito and was crying because she thought I was homeless and kept babbling
 
Back when I was homeless, all I had to my name was this beautiful double-sided silver ladle left to me by my dear old grandma. It wasn't much but it was the only thing connecting me to my past life, and my humanity. One day I'm sitting there eating my coconut with it, and left it there for like 3 minutes to go shit in the bushes. I come back and it's gone. Some fucking asshole stole it, I mean who steals from a homeless person?
 
A random black homeless man randomly telling me that he sucks dick when I walked by him.

Good to know.

Oh, and an awkward and uncomfortable conversation I once got trapped in where some man told me that a woman he loved committed suicide, and he invited me to go in his van.

As soon as a woman walked by, I left and pretended to know her.
 
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Got up to leave for work, we carpooled, and a piss reeking homeless guy pops up from the back seat from under jackets and shit like a jack in the box and he's like "hey, goodmorning, how are you"
It had stormed pretty badly and he abandoned his shelter for my coworker's truck
 
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A buddy of mine was throwing a BBQ one time. Her backyard opened onto an alleyway and there was a lot of people there and not everybody knew eachother. One of the people there had this little dog that seemed to generally like everybody except for this one guy. Nobody really thought much of it and nobody really questioned who this guy was. I stopped by my friend's place the next day and it turns out the guy was some homeless dude who'd wandered in out of the alleyway.

When she'd gotten up in the morning she found the guy in the backyard cleaning profusely. Apparently it was spotless. My friend asked him what he was doing doing and he told her he was cleaning up and showed her all the 'treasure' he'd found after cleaning up all night after everyone left. He pulled a bunch of stuff out of his pocket he'd found on her lawn. Some joints, cutlery, coins and shit like that. It turns out the guy was also a meth head who had apparently been clean for a day. My friend's a pretty nice person so she ended up telling the guy he couldn't keep the stuff, he gave it back, and her and her boyfriend took the guy out for breakfast and pretty much politely told him never to come back.

My version of the story kind of sucks but the way she described finding the guy cleaning the shit up in her yard was pretty fucking funny and surreal. Apparently he did a really good job cleaning up and didn't actually end up stealing anything in the end.
 
A tranny sleeping in the bushes behind me building. One of my neighbors was dumb enough to let shim sleep on the couch, until we all asked him what the fuck was wrong with him. A few days later, he got rid of shim.
 
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