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Delivery Drivers Share Wild Stories From Deep in the Trenches

Delivery drivers are some of the most essential workers out there. They brave the elements (and shitty tippers) to bring food to people who can't go out and get or make it - and they do the same for lazy sacks of shit like us when the munchies strike or a hangover needs something fast and greasy. Knowing the varied states in which people receive their orders, it's no surprise that these heroes have their fair of wild, weird, and freaky stories from their many trips. This Reddit thread is chock full of some of the craziest experiences delivery drivers have been through. We've pored through it to grab the best and most bonkers. But if you really like to read, go check it out yourself.

  • 1
    Font - benito823 ↑ 61 ..• 10h I had a delivery to a hotel that was crawling with hookers. The guy told me that he had his money in the trunk of his car that was right next to mine. He told me that he kept it there because you can never be too careful, and then he pulled out a very small gun and turned toward me and repeated that you can never be too careful. I took a step back and he said, "Ah, I shouldn't have done that" and then paid me.
    Via Reddit
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  • 2
    Font - Oluja 1 690 .• 13h I used to deliver Chinese food. I was a 19yr old female, so I had my fair share of creeps hitting on me, or drunk guys grabbing me, but nothing that ever made me feel unsafe. I was also the only driver, so all of the regulars knew me, and I knew all of them. This one time, I went to a house l'd been to before, but it was a different unit in the house. A guy was standing out in the front yard. It was like ten degrees out, so that was weird. I parked and took the food ove
    Via Reddit
  • 3
    Font - He insists that he tips me, and starts saying "just come up with me and l'll get you some change." And I'm already creeped out, and I keep telling him it's really fine. Then he goes "come on, I'll see if my girlfriend has change." That, of course, puts me at ease. If he's got a girlfriend in his apartment, he's probably not gonna rape me or anything. So I follow him up these stairs at the back of the house (on the outside; he had the upstairs unit) and make a point of staying outside whil
    Via Reddit
  • 4
    Font - Chalky_Cupcake ↑ 128 10h I delivered a Numero Uno pizza to Ron Jeremy at a Comfort Inn on Ventura Blvd in Woodland Hills California. He answered the door in bathrobe and behind him there was lighting set up and other people. He walked me to his car in his robe to get his wallet which was under a case of Today Sponges. Every word true and not a single moment was awkward or weird. It was epic and i felt like i had grazed a piece of history.
    Via Reddit
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  • 5
    Font - deszinck 1 347 14h Used to deliver flowers. Once delivered a bouquet to a (half naked) prostitute in a brothel. When I handed it over, she read the label and legit laughed out loud... I was 16 and kind of terrified, so I just hurried outta there and told my employer not to send me there again! Edit: In my employer's defence, she had no idea it was a brothel!
    Via Reddit
  • 6
    Font - Rulybear 1 180 10h Man there was a strip club that we delivered to. I used to love delivering there. Not because of the topless girls, but because of the tips. I delivered once and was told she was on stage and that I could watch while she finished if I wanted to. So I did. Once the song finished she walked over to me and gave me all the cash she had in her g-string. It was like $35 for a $14 order.
    Via Reddit
  • 7
    Font - 2cool4u6969 ↑ 646 .14h As a pizza guy in college, I had a gun pulled on me as a 'joke' at the door. Guy opened up the door with what looked like probably a .45 or something pointed in my face and said something like "Who the f. are you?" His wife and two young kids were standing behind him and everyone had a biiiig laugh at my expense. Not surprisingly, he gave me a shitty tip and then immediately went on the DO NOT DELIVER list.
    Via Reddit
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  • 8
    Font - SixlnchKidsMeal 1 136 .• 12h Was a delivery driver in a small town. Lots of rural areas nearby. Delivered to a guys house that was down a dirt driveway and kind of hidden by trees. I get to the door and it's an older man maybe in his 50s or 60s, grey hair, and he's leaning like he was drunk or something. I believe it was the weekend but it was early, probably 4 or 5 o clock, but he was so fuked up he proceeded to ask me about 3-4 times what he ordered, to which I read the receipt back to
    Via Reddit
  • 9
    Font - Another time sticks out in my mind where delivered to this guys apartment and he was maybe in his late twenties, lived alone with a cat, and was also drunk in the early day (this time I wanna say it was more like 1-2 o clock on a Sunday). He seemed like a cool guy and said he worked on video games and was into computers and stuff and we had like a 5-10 minute conversation and he said he thought I was really cool and we should hang out sometime. He also seemed kinda cool but also lonely an
    Via Reddit
  • 10
    Font - CactusWildChild 1 250 .• 12h I do delivery for a deli/pizza/ice cream shop. This happened just the other night. I was greeted at the door by a 40Olb hairy man wearing nothing but a pink tutu. Thank God his family jewels were hidden. As he's signing the receipt, I hear a woman ask if it was the food and he confirmed. Out of nowhere comes this woman wearing a full Furry squirrel costume (head and all) and hands me a $20 tip. Meanwhile, both of them are standing there nonchalantly, checking
    Via Reddit
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  • 11
    Font - NWA-Throwaway8510 1 60 9h So this didn't happen "at the door" but in the house. I used to deliver helium and balloons. Mostly wholesale to party stores and such, but occasionally to an individual for a party. I had to deliver to a lady with loads of health problems one time. She was legally blind, in a wheelchair, and had several brain surgeries I believe. Once I deliver the helium tank and balloons, I explain how to set it up, and attach the nozzle and I place her hands where she can fee
    Via Reddit
  • 12
    Font - As l'm getting ready to get the signature and leave, she starts talking about her brain surgeries and how she has a hole in the back of her head. I try to be polite, but dismissive and get on my way. But she is having none of that. She insisted I touch the hole in her head so I can see what she's talking about. I obviously politely decline and she presses further. She reaches out and grabs my arm and guides my hand to the indention in her skull - all in one swift motion before I can react
    Via Reddit
  • 13
    Font - glitter_gore_alien 1 31 9h Female delivery driver here. I delivered to a motel a couple of weeks ago. The guy answers and backs up a bit, looks me up and down and goes "Oh, you're the pizza lady, eh?" with this really creepy tone. I ignore it, and just tell him the total. He props the door open with a chair, and it looks like he's just going to get his money and pay. He pulls out his phone though (a flip phone, presumably a burner) and I swear the way he held it when he was looking at it
    Via Reddit
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  • 14
    Font - carsonshall ↑ 36 9h I delivered pizza when I was in high school about 20 years ago. One night I delivered a pizza to this gorgeous woman wearing a red satin night gown, she asked me to come in and put the pizza down, she then went and sat down on her couch and offered me wine. I turned it down because I was working and had to get back to my job. She then went into her purse to give me the money, and again asked if I wanted some wine and said I could have some pizza too. I said I wish I co
    Via Reddit
  • 15
    Mammal - starshine913 ↑ 265 14h ooh..or the delivery instructions i had once: "barn lights don't work, come around back" when i get to the back of (what looks like an abandoned) barn this man is in the pitch black, smoking a cigarette, in a lawn chair...
    Via Reddit
  • 16
    Font - NGGJamie 24 9h I got chewed out by this alcoholic woman in our delivery area once. She called us up, I took her order myself, and sent it on its way when it was ready. I got a call from my driver a few minutes later, and the alcoholic was saying she already got her order. I was slightly confused because we weren't so busy that a doubly-made order would slip by me. I checked with the other drivers just in case, nobody else had gone that day. She did, however, order the same exact thing the
    Via Reddit

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