What is your weirdest homeless encounter?

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I was 17 and walking through downtown to work. Getting off the train, I passed by the usual hobo strip by the 7-11 and was relieved I made it past without an encounter.
The next two blocks were empty and in the middle of a sunny day, a bloodied hobo jumps out at me. Not another soul in sight.
I froze and and he came at me screaming CAN I HAVE 10 BUCKS
I only had a toonie and threw it at him. He said THANK YOU and hopped across the road like an athlete and disappeared.
Never seen him again but did not work there for much longer after that.
 
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I was in Hawaii about two years ago for a bit with Mr. Devereaux and we stayed in Honolulu for a few days with friends. This was when the housing crisis there was going from bad to worse, right after Lahaina burnt up, so there were tents and folks sleeping on sidewalks pretty much everywhere you went. For the most part these poor folks were genuinely keeping to themselves and not bothering anyone, not panhandling, just trying to survive while homeless and it was honestly heartbreaking. I spent the first 20 years of my life in a major city in the Northeastern US, where the homeless are aggressive and will chase you for the change jingling in your bookbag, so it was jarring and felt more like a war zone than homeless encampment.

There was only one true generic-issue schizo hobo I noticed in Waikiki that time, who very closely resembled Vermin Supreme, but he was only notable to me because he stuck out compared to the rest of the homeless community there. He had a broken bottle in his hand and was waiving it, and was yelling in schizo tongues at an audience of enraptured Japanese tourists. Just an odd sight.
 
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Got two for ye, when I was younger I had a flat tire and while I was changing it a homeless drunk came up to me and started bemoaning to me his sad life. Finally he stopped talking to me and walked into the street to harass drivers. The second was when I was driving home from the gym and the local homeless man yelled at a guy in a convertible He screamed "I'm going to tear your ass apart 6." the guy in the car had a 6 on his license plate
 
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I worked a job where you had to walk far into the property to get to a bathroom that would very clearly be employees only, so I was shocked when I opened the unlocked door to a single person restroom on the inside of a building used for storage to find a crack whore shaving her legs.

She immediately said "can't a women get a little peace around here" and then asked me if I'd sale my headset, because she wanted it and "would be a millionaire when the money for her record deal came in".
 
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Idk if he was homeless or just nasty looking but a guy pinched my ass infront it of a Starbucks and I hit him with my purse. The Karen's drinking their adult milkshakes threatened to call the police. Pn me. For hitting for some poor homeless guy who didnt do nothing.

Yknow, except sexual harassment.
 
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One day, while I was eating at a Korean restaurant, I saw a hobo through the front window absolutely chimping out on the sidewalk. He was throwing his arms around, dancing, hollering- just going wild.

Eventually, one of the workers came outside and asked what the fuck he was doing, and the hobo shouted, “I’M PUTTIN’ A CURSE ON THIS PLACE!”

He eventually left, and the Korean place is still there, so I guess the curse didn’t work too well.
 
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These aren't the "weirdest", per se - but they make for easy reading:

I had some singles fall out of my pocket while at a gas pump in one of those meth-ravaged San Joaquin Valley towns I was passing through on my way to a national park, and an opportunistic bum ran up to scoop them up while yelling "Oh bless you, sir!." After deciding that Californians would likely prosecute me for punting him in the head, I watched him run in and buy a bottle of Windex, off of which he promptly unscrewed the spray nozzle so he could begin chugging it before he had even made it out the door. He met my eyes again, and we gave each other a thumbs up which felt more sincere.

On another occasion, I was checking out of a formerly nice hotel which had utterly gone to shit during the pandemic; now allowing vagrants to infest the lobby during Starbucks hours. I had to pass through a group of them on my way to the connected parking garage, and one with multiple hospital bracelets called out to me to say, in a forlorn manner, "Sir, please: I don't know my name, and my ass hurts." I turned back to reply "You probably had a stroke", to which he smiled and nodded in a way I can only describe as being how a complimented fat child would.
 
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Blanche Devereaux said:
I was in Hawaii about two years ago for a bit with Mr. Devereaux and we stayed in Honolulu for a few days with friends. This was when the housing crisis there was going from bad to worse, right after Lahaina burnt up, so there were tents and folks sleeping on sidewalks pretty much everywhere you went. For the most part these poor folks were genuinely keeping to themselves and not bothering anyone, not panhandling, just trying to survive while homeless and it was honestly heartbreaking. I spent the first 20 years of my life in a major city in the Northeastern US, where the homeless are aggressive and will chase you for the change jingling in your bookbag, so it was jarring and felt more like a war zone than homeless encampment.

There was only one true generic-issue schizo hobo I noticed in Waikiki that time, who very closely resembled Vermin Supreme, but he was only notable to me because he stuck out compared to the rest of the homeless community there. He had a broken bottle in his hand and was waiving it, and was yelling in schizo tongues at an audience of enraptured Japanese tourists. Just an odd sight.
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Hawaii (big island) has some of the worst homeless I've seen, and I lived in Portland for nearly 10 years. Was only in Hawaii for a few months, but I did rough it there a bit to be adventurous. And the bus was free at the time, so rode it a bunch and got to see stuff like a homeless gang harassing a poor female bus driver until she was about to lose her mind.
Off the bus I saw a woman piss right in the middle of the sidewalk/day in downtown Hilo. Near where a big, very dark guy just sits out in the sun all day. Saw a crazy fight in the main Hilo park between some native dudes, where one dude kicked the other dude square in the jaw and the kicked dude wasn't phased at all. Never fight a Hawaiian! Saw this rough old homeless tweaker lady get kicked out of walmart and I felt bad for her so I gave her a $20 bill I happened to randomly find on the ground the night before. She took it like I handed her a match or a nickel or something. Lol. And then asked for help crossing the road. Guess I learned something there.
Also lived in a junkyard there for a while...it was described on craigslist as a coconut farm work trade, but was a madhouse with some really interesting but crazy people living there. And lots of really good food because the owner was a native guy who got hooked up with stuff that grocery stores were going to throw out (but was still really good.) I'd kill 2 or 3 pounds of Hawaiian lychee a day easy. There was this Japanese guy living in a bus there who was about 80 and would laugh at nothing hysterically with his dog in the bus a few times a day. A German Jew who was about 75, nearly blind and barely able to get around with a cane (but she would navigate this crazy junk yard, walking over jutting lava rock, roots etc. to go live in her little shanty. She talked about her family helping the Nazis, walking barefoot through India in the 60s, helping a bunch of African guys get citizenship in DE by having babies with them, wanting to be a psychic, etc. There were a couple of younger degenerate alcoholics who were fun, funny dudes except when they drank -which was often. There was a local couple - big white woman and skinny native dude who seemed nice but turned out to be really twisted. I'm pretty sure they were eating these sweet Airedale mix puppies, including the one I gave them because I felt bad that theirs had died (before I saw the pattern.) Owner eventually kicked them out because they never wanted to do any work.
I've roughed it around the globe, inspired partly by Vagrant Holiday, so I have seen lots of homelessness of all kinds. Even slept in parks in Japan (which they actually allow, if you are respectful about it.)
 
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None of the hobos in my area are violent, though maybe it's only because I generally meet them in broad day. I had a conversation with one, who was wearing a woman's dress, his ID picture was taped over with electrical tape, he told me that California was actually just a cave and that he was trapped in a rape dungeon for years. After a long rambling "conversation" I gave him an orange and made my exit.
 
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When I was a kid I gave a homeless guy $20 and a few minutes later saw him exiting a liquor store with a 6 pack in his hand. Weird at the time because I thought he was gonna buy food
 
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Blanche Devereaux said:
There was only one true generic-issue schizo hobo I noticed in Waikiki that time, who very closely resembled Vermin Supreme
Click to expand...
I genuinely am sure I know who you are talking about. On that note, also in Waikiki. I was out on a jog at the time, during covid the homeless situation was really bad because cops didnt seem to give a shit....most of the time.

While I was jogging on the Ala Wai sidewalk, some fat guy was ripping some small woman out of his apartment and beating the fuck out of her. I stopped and stared, started calling the cops. He starts pulling her down the street, he noticed I was following close behind and yelled that he'd beat my ass. As if, fatty, I could speedwalk away from you. Anyway, the woman had a syringe visibly sticking out of her arm and she had a dumb smile the whole time he was hitting her. As I followed close behind, the guy kept yelling at me. I wasn't going to let this fat retard abuse this woman for presumably taking his drugs, idfk. As fatty is walking backwards though, yelling at me while tugging the woman, a cop car spawns behind him. I wasn't the first to call, clearly. So im close enough at this point to hear the conversation with the cop. The cop tells fatty "youre okay, you can leave i just have to take the woman in custody". Fatty, fully enraged and unwilling to look a gift horse in the mouth tells the cop no, thats HIS woman. The cop did not see fatty beating up on her just yelling at me at this point. Cop tells him no you need to fuck off. So fatty got mad and squares up....what does he do? Punch the cop? Threaten the cop? No, he turns 90 degrees to his left and socks the woman a clean one right in front of the cop. The fuck, why? Anyway naturally the cop said something along the lines of "ok now I gotta take you in" and pulled out his tazer, tazes fatty. Immediately fatty drops to his knees and starts literally crying and begging the cop not to do it again. By now I figured id better just gtfo and let the cop do his job.

To this day, I am absolutely mortified of getting tazed because of how fast that fatfuck went from wanting to fight the whole planet to begging and crying on his knees. I dont know how bad it is but holy shit that looked bad.
 
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For some retarded reason I decided to visit Washington DC and see all the big sights. I was in between tourist traps, having a cigarette when a homeless guy approached me and asked for one.

I gave the guy a smoke and let him use my lighter. Upon giving me my lighter back, he got down on his hands and knees and blew cigarette smoke on the ground, stating that "The Earth likes to smoke to.".
 
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Let me tell you about The Bradlees Penis Man.

I was in my car with my friends when we were teenagers in front of this store, Bradlees, and my friend was telling us about a semi-homeless retard called The Bradlees Penis Man.

He told us that The Bradlees Penis Man goes up to teenagers and children and he's too retarded to talk, he just looks at you, grunts, points at his crotch, points at you, and then points behind Bradlees, indicating that if you follow him he will do something with his penis and it will involve you.

I'm thinking this stinks of urban legend but my doubting thomas ass was immediately proven wrong when I see a grunting retard at my driver side window not seconds later. I roll down my window a little bit and he just starts doing piltdown man grunts, desperately motioning to his junk and trying to get us to go out back with him.

I'm dying laughing as I drive away because it was funny but also because that was the second time that year my friend had just kind of summoned an urban legend into existence like that.
 
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>be me
>just worked out at gym in strip mall
>wearing sweatpants and wifebeater
>it’s kind of chilly out but idgaf, my cold tolerance is high
>gym is in area of town near a homeless encampment
>don’t care, crackheads don’t bother me
>it was leg day and I needed to eat protein immediately
>go to dollar tree next to gym
>buy like 6 tins of sardines
>cant eat them in car cause if any of the water gets out it’ll smell forever
>sit on sidewalk, pull camping fork out of pocket
>guy walks by, drops $20 in front of me
>I am not homeless; I make good money
>don’t say anything because my mouth is full of sardines
>pocket the money
>use it to buy more sardines the next time I go to the gym.
 
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