Shocking Delivery Service Surprises

January 5, 2022 | Derek Choi

Shocking Delivery Service Surprises

Delivery workers often see a wide range of people with all kinds of tastes. Weird food, odd houses, or awful neighbors, they’ve seen them all. Sometimes, these encounters leave a lasting impression, creating a story that wants to be told time and time again. These 50 Redditors share times their deliveries took a strange and unexpected turn.

1. Joining The Masters

I took a big pizza order to a college dorm. It was just under $200. When I go there, I knew the code to get in because I had been a dorm head in the same building a few years earlier and there was one door with a code instead of swipe card. I knew exactly where the room was, so I knocked and the guy opened it and said "hold on" and closed the door.

I heard an alarming amount of movement in the tiny dorm. I was getting nervous—but I was in for a surprise. About two minutes later, they opened the door with no lights on. In the dorm was around 15 dudes all in cloaks and holding lightsabers. One addressed me as Master Jedi. I was laughing so hard I almost dropped their drinks. They tipped like a hundred bucks and said I could join their club anytime.

It was amazing.

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2. An Unexpected Meal

I worked for Uber Eats. One time, I picked up the order and pedaled to the delivery address. Once I get there, I ring the doorbell and no one answers. I start sending my message and wait for someone to respond. Two minutes later, a very distressed woman comes out screaming expletives at someone inside the house and left in her car.

The person at the door, who was only in his undies, proceeds to slam the door. I just stood there speechless. I let 30 seconds pass and ring the doorbell again, no one answered. I sent another message and I was ignored. After 10 minutes, I contacted support and they told me that if they didn't answer in five more minutes, I was free to leave with the food.

I waited the five minutes, texted support to let them know, and then drove back home. My girlfriend and I had a feast. We googled the cost of the meal and it was close to around $100, which is a ton for only two people. We were in a very rough place economically then, and it ended up being the best meal we had had in months.

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3. Lower Than Expected

I was delivering a pizza and after I knocked on the door, I heard a faraway voice yell "coming!", so I waited. After about a minute, I hear the same voice a little closer yell "almost there just wait!". This continues for several minutes, with the voice coming closer and closer until the person finally reaches the door and opens it.

I'm expecting to see someone at eye level, however instead I'm greeted by a smiling person on the floor who had no legs and dragged themselves across the house to answer the door. I offered to put the pizza inside for them in the kitchen and they were pretty appreciative.

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4. Is It Halloween?

I delivered like five pizzas to this guy once. I had to ring the doorbell several times before he came to the door. When he got there, he didn't really say anything except to come on in really quick. Now you aren't supposed to go into people's houses but I thought “Who cares, I can defend myself”. I get inside this guy's huge house. I was not prepared for what I found.

There was a full suit of armor right by the door, and somewhere he had this Halloween CD playing creepy, deep-voiced laughs. While he's searching for his wallet, the biggest dog I've ever seen walks up to me and falls at my feet pushing me over. I'm sitting next to a suit of armor petting this huge dog waiting for this man to pay me.

He gave me a $40 tip.

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5. A Famous Delivery

Finished a Postmates delivery in the Hollywood Hills when I got pinged to pick up an order at the Starbucks. I liked delivering in this area because usually the tips were very, very good. The person ordering wanted four tall iced coffees...with no ice. I shrug that part off because rich LA people are all weird, but I was annoyed because I had to place it, which means I had to make those annoying requests instead of just picking up the drinks.

I go into the Starbucks and the lady working the counter says “We’ve been expecting you...” and I was like “...Ok?” Now it's starting to get weird. Usually, if you have to place the order, the restaurant would not be expecting you. Then, she tells me that this is Ariana Grande’s exact order and that I will be delivering to her house. It wasn’t her name in the app, but it did occur to me that a celebrity of her caliber probably uses an assumed name or has an assistant order for her.

I still had my doubts though, just because I'm a naturally skeptical person. When I got to the address, I had to enter a key code at the gate which wasn't unusual for this area. But when I saw the view and saw that it was basically its own compound of multiple different houses, I figured that even if it wasn’t Ariana Grande’s house, it had to be someone obscenely rich and famous.

I pulled up to the house number specified in the app and texted that I was there, per the instructions. The person who greeted me was a middle-aged 4’10” woman with a limp. She said thanks and I left.

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6. A Slippery Situation

I used to deliver for Domino’s and was delivering during a night with freezing rain so it was very slick. I get to this one house with a steep driveway way, and there was no way I could drive up. I tried multiple ways to walk up the driveway, even on the grass, but I could only make it a few feet. I call the customer and explain the issue, then they come out with a rope and I tie the pizza bag to it.

They end up using the rope to pull it up the driveway, put the cash in the bag with a nice tip, and slid it back to me.

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7. What Are Those For...?

One time during the early days of the pandemic, I got an order for like a ton of BBQ ribs from some newly opened restaurant in Atlanta. I got all this food drove out to some random upscale Hilton Hotel off the beaten path. After a ton of back and forth with the concierge, he finally directed me to the correct room.

I finally reach it only to be met at the door by two unclothed folks and another two more “waiting” on the bed in the hotel room. I’m not saying those BBQ Ribs were going to be used in whatever I interrupted, but I can’t definitively say there wasn’t a connection.

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8. Home Alone

I had a delivery to a mansion of a house, but when I get there, nobody answers the door or answers the phone number listed. As I'm about to give up and go back to the store, three 10–12-year-old kids run up saying they ordered the pizza and their parents were out of town. But that wasn't all. While the parents were away, they taught themselves how to make homemade smoke bombs which they used to inadvertently set their backyard on fire.

I grabbed their hose and started putting out the fire, they didn't want to call the fire department in fear of getting in trouble, but I made them do it. By the time the fire truck pulled up, I had taken care of the flames and the kids emptied all three of their pockets into my hands for about a $40 tip.

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9. A Matter Of Taste

I used to deliver pizzas, and one time I arrived at a house at the same time as a driver from another pizza place. We looked at each other confused for a second before we went to the door. Turns out they had some people over and one of the people there really liked one restaurant over the other, so much so that they ordered pizzas from two different places.

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10. Stuck Inside

My wife and I have done Uber Eats, Door Dash, and Instacart for about two years now. We don't have too many unique stories, mostly just high, buzzed, or weird people answering the door. My wife is in a few Facebook groups though, and we just heard about a woman who was delivering some food into a private, gated home.

The gate had to be manually opened by the homeowner and he let her in no problem, but then after she delivered the food, things took a dark turn. He wouldn't let her leave. It took calling the authorities, them arriving, and filing a report for her to be able to leave and learn that this was the third time he's done this. Uber, though, won't ban him from their service.

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11. Baffling Buildings

The app told me to pick up the food by 7:05. I drove right to the store, got the food at around 7:03, checked the app for drop-off instructions, and it said "deliver by 7:00". Okay. Whatever. I got to the address at around 7:20. The building I needed to deliver to wasn't there. I walked around a bit and it was nowhere near where my map took me.

I called the customer and said "Hi, I have your food but I've been walking around for a bit and can't find your building. Can you walk me through where it is?" They just said "okay" and hung up. I texted them that I can't deliver the food if I can't find their building. No response. I walked around for a bit more to find the building and I couldn't.

I called the driver support line to explain what happened. As I was dialing, I got a text from the customer telling me where their building was, but this was 15 minutes after I first told them I was lost. It was a completely different place than where the app took me. I drove there, dropped off the food, and questioned why I bother doing this job.

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12. Chip Confusion

I drive for Uber Eats and one time someone ordered food from a healthy vegan restaurant. Except I saw that the order was eight small bags of chips. Not even anything off their salad menu, just eight bags of chips. Then while I was on my way to deliver it, they messaged me twice in the app. The first time they said "Please", and the second message was "Be Careful".

To this day I have no idea what was going on, or why they didn't go buy chips from the convenience store near their house

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13. Who Are You Again?

Once I picked up an order from a Graziano's and the restaurant had no idea what Grub Hub was or that they were on the app. I had to call the horrible customer service and deal with them for like an hour before the restaurant believed it was real, then they gave me the wrong food. I only stayed in that job for a year before I realized how completely disorganized Grub Hub is, at least in my area.

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14. Staying Frosty

My boyfriend and I used to do grocery delivery. One time, I had a woman order 33 oranges. Another time, he had someone order 24 jars of vanilla frosting. The store didn’t even have enough vanilla frosting in stock to complete the order. Then one week later, we saw that the same man placed another order for 20 more jars of vanilla frosting.

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15. Porky Problem

I pulled up to this easily $1.5-2 million house. A lady opens the door and as she's signing the receipt I hear, "Bethany! Willis is in the dog food again!" This is deep in Louisiana, so this is all in a typical southern drawl. I look behind her and see a man chasing a full-grown pot-belly pig wearing an LSU jersey away from what I assume is the dog food area. Willis returned to the area shortly after.

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16. Share Your Number?

I deliver for Uber Eats, and last week I was delivering some wings to a dude. Simple delivery, leave at door, no contact. I compete the delivery and a couple minutes later my phone rings and I could tell it was coming from the customer through Uber. I thought something was wrong with the food, but no, he called to thank me for delivering his food.

Then my phone rings again. It’s the same number, and I ignore it, so he calls again, and I ignore. Dude calls again, so I finally answer and he asked if he could have my number for future orders and I told him I didn’t think that would be appropriate and ended the call. I did a couple more deliveries after his and when I finally got home, I get on Facebook and this dude tracked me down and sent me a friend request. It was so creepy.

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17. A Different Place

Many years ago, I was a driver for Pizza Hut. We had someone place an order, and their home address was saved to our system but in the notes, it said to deliver it to a hotel literally down the road from said home address. So I go to the hotel, knock, and a dude answers the door in his boxers with a girl in bed peeking around to see who was at the door. I’m 99% sure I walked into an affair encounter.

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18. Big, Bad, Pit Bull

I work for Uber Eats on top of my part-time job. About two months ago, I was dropping off a Chick-fil-A order at a house not too far away from where I live. It was a pretty standard meet-at-door delivery. As soon as I pull up to the house, I hear my customer yelling "Nala, no!" This giant pit bull, who I can only assume was Nala, comes barreling towards me as I'm taking the food out of the delivery bag in the backseat of my car.

I thought the dog was just coming to say hello to me, and I like dogs, so I didn't really mind. My own dog is excitable, too. I was very wrong. This giant dog leaps into the backseat of my car, looking around, jumping, doing all sorts of dog stuff. The customer and I spent the next few minutes coaxing the dog out of my backseat. He apologized profusely and increased the tip in app.

I wasn't actually mad about it, it's my favorite delivery story to tell by far.

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19. Billowing Smoke

A few years ago, I was working for Door Dash. I got an order for 27 slices of bacon from Waffle House. I thought it was a mistake, so I text the customer and they were like "Yeah man that's what I want". I get the order and drive to their place. I knocked on the door. When he opens the door, smoke comes pouring out of the house.

There was so much smoke I thought the Undertaker was there. There stood a man that was high as a kite. He goes "Mannnn....I'm so glad you're here...I'm starving....” I was like “Oh I noticed”. I gave him the food, started walking away, and hear him yelling "You’re a hero mannnnn!"

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20. My Very First Day

It was literally my first day doing deliveries, so I punch the address into my phone and arrive as quickly as possible. Neighborhood is a bit shady but I don't judge. The note on the door is in really bad handwriting, but it says to knock because the doorbell is broken. A guy opens the door: old, scruffy, skinny white guy.

He says to come to the kitchen, because that's where his cash is. At that moment, I realize I shouldn't enter a stranger's house, but I didn't really have an excuse ready, so next thing I know I'm in room? That's what it should be anyways, but it's full of retail clothing racks full of clothes and a couple mannequins.

Needless to say, I started to panic. Thankfully, we get to the dimly lit kitchen where the money and a cat are on the counter. He shuffles through the cash, pays me in exact change, and just takes the pizza to another room. So, I walked through the store to the front door, and left. Now, I always have an excuse ready.

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21. Not What I Expected

I dropped off porta-potties for a while. I pulled up to some farmhouse out in the middle of nowhere, it was early morning and still dark. I knocked on the door in the unlit entryway and a chubby little toddler answered the door rubbing his eyes. I said, "hey little fella, can you get your dad?" He responded in a grown-man voice: "I'm a freakin’ little person, jerk. Gimme the bill and drop off the potties."

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22. A Small Tipper

One time I went to a really nice house full of screaming, laughing kids, probably 8-10. It seemed like a birthday party, except there were no decorations. A kid answered the door, but he had gelled hair and was wearing a button sweater. When I asked for his parents, he just got a few kids to take the food while he busted out a wallet. He tipped me really well, smiled, then shut the door in my face.

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23. “Meow”

I just probably gave a delivery driver a story of their own tonight when they called me to clarify directions. Their number was the same area code as a spam call that I got the other day. I answered the call, and it actually had a human there and not a robot. So, I assumed it was them again, and when I answered the call, I kept saying “meow” instead of “Hi”.

Then they asked for me by name, like the last spam call did, and I just kept saying “Meow meow” every time he asked me something until he was like “Ma’am, this is your Postmates driver”. I wanted to curl up in a ball from embarrassment.

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24. Not That Much Of A Screw-Up

I delivered pizzas to a rec center for a kid's birthday. There were about 12 pizzas, and they were in the warming bags. I tried to carry all the bags at once, which led to boxes being slanted and the pizzas sliding into the corners. When I pass the pizzas to the guy, he opens them up and is super upset. He’s like, “I’m not paying for this”. which is fair.

Thing is, the policy was if you don’t like the pizza, you can either not pay and I take the pizzas back to the store, or I take the pizzas back to the store and then come back with new ones and you pay full price for those ones. The man told me, “Nah, I only have this place booked for another twenty minutes. We’re eating these, but I am not paying”.

So, I didn’t really care, but if he didn’t pay it came out of my wallet, so I called my boss, who was a very aggressive loudmouthed piece of work, and told her what was up when the guy grabbed the phone from me. This is when it started to get really messy. He and my boss begin screaming at each other over the phone for about five minutes! He hurled some insult about me at my boss, covered the mic, winked at me and whispered “I’m just kidding,” and then he hung up.

The bill was about $140, so he looked at me and said, “I’m giving you $70 dollars for the pizza, and I’m giving you $40 as a tip. Do not give that $40 to that awful boss you have”. So I went back to the store, told her he would only pay $70, and she said, “Oh well, at least we got something,” and I got a big tip even though I was the one who screwed up.

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25. Unorthodox Deliveries

The drop-off instructions for the delivery said: "Text me when you arrive, and come to the side of the house. I broke my leg and I can't come downstairs, but I'll lower a backpack down to you on a rope. Your tip is in the loop on the back. Thanks!" I thought it was a setup, but the instructions turned out to be legit. I thought it was amusing!

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26. Not The Only One Delivering

I saw a woman give birth. I was delivering for a pizza place at the time, and we delivered to a large children’s hospital about a mile from the store. I pulled up to where we normally delivered, the valet loop, and a blue F150 comes flying in as I’m walking away. The driver jumps out of the truck screaming that his wife is giving birth, and out of the passenger side I can see plain as day a few millimeters of dilation staring me straight in the eye.

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27. The Ride-Along

I bring three orders out and the first one I get to I call, and no one answers, so I go to the door and start knocking. A handicapped young man in pajamas answers the door and steps out in the rain to get the food. Then the worst thing happened: Before I give it to him, I have to collect the money, but before I do, the door closes behind him, locking him outside with me.

Now he starts to cry because the door is closed, he’s locked out, and doesn’t have the money on him. His mom was sleeping in the bedroom with her door closed and junior wanted a snack. Now, I feel awful because I have to leave and keep delivering, but I can’t leave the food because he hasn’t paid, and he’s stuck out in the rain in his jammy-jams.

So, I make the decision to call the shop, and gave my credit card to pay for his order, and decided that he could ride with me on the next two deliveries and eat his food until I had a chance to figure out what to do. By the time we finished and got back to his house, I helped him bang on the door until his mom made it to the door and let him back in.

First thing he said was “Mom, I delivered pizza!” I felt so relieved I didn’t bother collecting his bill. But I can tell you this, anytime Jack wants to go on a delivery, I’ll be happy to take him!

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28. What’s Your Price?

I delivered pizzas for years. There was this one house that I just dreaded going to. It was a tiny little house, and they had a tiny little dog, and the dog made messes all over the floor. It was just everywhere. The woman who lived there was absolutely nuts. She shouted at the kid on the phone who took her order, and she shouted at me.

I'd hand her the pizza and she'd shout that I probably messed it up. It'd be right and she'd say "Well, okay then" and she'd give me a $15 tip. Come to find out, I was the only one who would go there. None of the other pizza places in town would deliver to her, and none of the other people at my Hungry Howie's would deliver there.

That's when I learned that my price for allowing myself to be shouted at was $15. After I had been there a year, she stopped calling. Then, the house was bulldozed. Now there's a pizza place where she used to live. And it's ironically pretty bad.

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29. More... More!

I was a pizza cook as a teenager. A customer asked for a pizza really spicy. I tried to explain what I could do to help make it spicy. He cut me off and told me to grab the extra spicy red pepper flakes and just shake the bottle for a while. I remember being a bit offended by his attitude. I opened the glass shaker of red pepper flakes and coated the sauce layer.

Every single inch of the base was coated with a layer of red pepper flakes. I baked the pie and delivered it on its way fully expecting to get a complaint when I would then arrogantly tell him that I was instructed to make it as hot as possible. The joke was on me though. They never called to complain. Now, more than 20 years later I still wonder how hot that pizza was and if they wound up eating it.

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30. Just Following Instructions

I use to make deliveries last year to make a little extra money. So, one day I got an order to deliver to this house. The instructions said "When you arrive, bang on the door very loud or I won't be able to hear you", so I walk up to the door and I proceed to knock on the door. The order is contactless delivery so I set it down on the doorstep and start to walk to my car. After that, everything happened so fast. 

All of a sudden, I hear the front door open and some guy comes charging out of his house straight toward me. He grabs my shirt and starts yelling at me telling me never to knock on his door like that again. I was taken aback, but I told him the notes he put said to knock loud. He doesn't even acknowledge what I just said!

He just continues to say that if I knock on his door again, he'll kick my butt. I pulled myself away and told him not to worry because no one will be back to deliver to him again. I got in my car and left.

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31. Sweetening My Day

This one person ordered like 10 specialty cupcakes from a nearby French bakery, and left a $10 tip. When I got to the door and rang the bell, I heard a ton of little footsteps running toward me. When the door opened, five kids all under the age of like 10 were behind it, and they looked absolutely delighted. The youngest one kept saying "Cupcakes, cupcakes!" all super excited.

The one who looked like the oldest boy gave me hug and thanked me for the cupcakes. After I'd handed the order off and waved goodbye to the kids, I honestly felt super warm and fuzzy.

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32. Impromptu Address

The order was for four kilograms of BBQ pork. The address is barely in our delivery zone, but in an underdeveloped area. Google maps even has it as an empty lot. If it wasn't already paid by credit card, we may not have delivered. Anyway, our driver gets there and surprise, surprise it's an empty lot. He calls the guy and he tells him to come to the back of the next building.

He goes and finds the guy. The dude has rigged up a projector on the back lot of an empty building and he and his friends are watching soccer!

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33. Just A Quick Break

I was a pizza delivery boy back in high school. I was delivering on Super Bowl Sunday during my senior year and one of the houses I delivered at felt bad. They told me to come in and watch the game, so I stayed there for a while. I watched a full quarter before going back to work. I knew that I was leaving for college soon enough anyway, so the possibility of getting fired didn't faze me.

My boss asked me what happened, I told him the truth, and he kept me around. I continued working there on breaks from college and, 15 years later, I am still friendly with my old boss. He works at the same pizza place and I go there with my family sometimes.

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34. The Compliment

I delivered pizzas for a few years in college. One of my deliveries to a hotel had a guy answer the door in nothing but boxers and a beanie. We trade money for pizza and as I give him his change, I hear another guy yell, unseen, from behind the corner, "if he's cute, let him keep the rest!" The guy at the door hands me back the change and smiles.

I wasn't sure how to react, so I just turned and left.

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35. The New Neighbors

The order said to go to house 21. Upon arrival, no one was home so I check the phone number. It wasn’t a complete number. After calling back work a couple of times I finally get the real number. The conversation roughly went: “Hey I’m at the delivery guy, no one seems to be home”. They respond “Ugh.... we’re out the front. You sure you’re at house 21?”

“Yes, I’m at house 21”. I then start walking down the street asking for landmarks. Then I hear “Oh I see you”. A boy about 11 years old comes up to me and takes the pizza. He mentions his family just moved in. He was actually living at house 18.

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36. Undercover Customer

I did Postmates back in like 2016 and one of the orders was for a pair of high-top white vans. I rolled up to the house and the guy invited me in for a drink, which I was thinking I should probably say no to in order to seem professional. The guy insists I come in for a drink until I cave. It turns out that he was the head of product for Postmates!

I ended up hanging out there for a while and chatting about working on the app, tech, the company and all kinds of stuff. It was very wild to feel like you’re getting punk’d.

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37. A Haunted House?

I knocked on the door, and a couple voices told me to come inside. When I opened the door there were weird cameras and lights pointing at me and a man and a woman sitting on a couch across the room. They knew I was nervous and confused, and they asked me to bring the pizza over to them. I walked the pizza over and the woman said "You just walked through a ghost". They were amateur ghost hunters looking for ghosts in a trailer.

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38. Curious About Cats

I delivered a pizza to a sketchy house. The guy who answered looked like a really crazy out-there weirdo. He asked me if I liked cats. I said yes, ready for anything to be sprung on me. He pulled out a baby Bengal cat that literally had six to eight toes per paw. Its feet were so big with the extra toes that it kind of looked like lynx feet.

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39. A Reasonable Mix-Up

I ordered some Wingstop, and after about an hour I started to wonder where my food was. When I checked Door Dash, I noticed my order had been marked as delivered, even though it never arrived. I filed a review saying it wasn’t delivered, and instantly got a call from the driver. “Hey man, I just gave you the food, and I even took a picture of it. Why did you mark it as not delivered?”

Turns out, the driver had another Wingstop delivery at the exact same time, with the exact same food, to a customer with the exact same name. The other guy with my name ended up with both of our orders!

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40. Red Flag Order

I had a delivery order from Subway that wanted only three water bottles. This immediately sends up red flags to me because I had another incident before this that involved a weird ex repeatedly sending water to his former girlfriend because she had a restraining order against him. In this situation, I thought it was weird because where this person lived was in walking distance of various places that could sell him water without a delivery fee.

It was also in a sketchier part of town and he picked probably one of the furthest restaurants in the city from his house. I ended up trusting my gut and released the order. I later mentioned it to friends and they actually knew who the person was because they had worked with him. They told me he ended leaving that job and was wearing an ankle monitor.

I don’t know exactly why, but him needing to stay home explains why he ordered water instead of walking to get it, but I’m still glad I didn’t go.

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41. Taking The Bait

I do Postmates in Sacramento on the weekends for extra money. On Super Bowl Sunday, I was working and I got an offer for McDonald's to a not-so-great part of town. I go to pick it up and it's a large drink, that's it. Huge red flag. I get there and the building looks as though it's abandoned, but the customer's note says to knock twice on the black metal door.

As I knock on the door, some dude rounds the corner and runs to my car and pulls the door open. I've heard of this happening before where they'll order something super cheap and have it delivered somewhere out of the way or in poorly lit areas. What they didn't plan on is that I bring my German Shepherd with me when I do Postmates and keep her in the backseat just for that reason.

I always make sure to put the customer's order in the warming bag outside the car before I get in the car, and don't take it out until I'm at their door. That way I don't have to worry about dog hair or anything. He changed his mind really quick about taking my car. I also didn't work much for about a month after that.

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42. What’s Really Important

One time, I got hit by a car right outside the house I was delivering to. My customer-first dumb mind still knocked on their door, scraped and bleeding, crying my eyes out, apologizing that their pizza got crushed as I fell down the hill. The lady said, "The pizza is not my concern right now". And I was so confused in the moment. I learned a very valuable lesson. You can care too much about customer service.

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43. Burger Benefits

I once delivered 10 bacon cheeseburgers, but literally just as I parked in front of the address, Skip the Dishes called me and said the order had been canceled. However, the guy at the delivery address was sitting on his porch and saw me and he just goes "Skip the Dishes?" so I say "Yeah but they let me know the order's canceled."

He tells me "Yeah you're the fifth delivery I've had, but this is the first time it's been canceled". Turns out he had gotten into a disagreement with a woman down the block and her way of getting back at him was by setting up a fake account for him and just delivery bombing him with ridiculous food orders.

Skip the Dishes must've been in the process of blocking the account just as I pulled up. Anyway, he and I laugh at how petty the whole thing is and then I accept my next order and start heading to the next restaurant. Thing is, I am now in possession of 10 bacon cheeseburgers. But I know just what to do.

I eat one, but obviously I can't eat 10 burgers so for the rest of my shift I got to be a hero by giving the gift of burger. Each time I would go to a restaurant to pick up my order I would give the restaurant worker a free meal. I also counter-offered a burger to a homeless person that came up to my car to ask for money; he seemed surprised but he accepted.

Eventually, once I was onto my last delivery at Montana's, I still had two burgers left. I gave them to a server working there and she just kind of melted, like she was seriously so touched, it was adorable. She was like "Really? You're just going to give me free bacon cheeseburgers? Oh my god thank you so much". I think she must've been due for meal break or something because it was so sincere.

Dumbest Ways They’ve Hurt Themselves FactsWikimedia Commons

44. Leave Them Alone!

I had a guy yell at me from inside his house to stop petting his cats. I dropped the order off at the door, took the picture, and closed out the order. Two cats had followed me up to the door and were rubbing against my leg, but I do business first before petting any animals that come up to me. I literally pet them for maybe three seconds before I hear, “Alright that's enough now” and a loud angry voice.

I felt kind of embarrassed but like c’mon, they were clearly happy to have a person show up. I thought maybe it could be because of Covid, but I’m literally handling the bag of food you ordered and driving it to you in my car.

Delivery Service SurprisesShutterstock

45. Tigers All The Way Down

I once delivered a sandwich to a big, ripped guy in a tight shirt that had a giant tiger face on it. As I hand him the bag I say, "You look ferocious in that shirt". He gives me a smile and starts to lift the shirt up to reveal another very tight tiger shirt underneath. We both laugh and I tell him to have a good one. He gave me a great tip.

Weird Delivery factsShutterstock

46. The Other Place Is Better

I was working at Domino’s pizza place, and I was told to deliver it to a certain place only to find that it was a competitor’s pizza place. I was cringing so bad when he picked up the pizza in the parking lot, he then started to head inside to eat Domino’s pizza at the Pizza Hut dining table! The cashier of Pizza Hut and I stared at each other for around a minute in disbelief before I left.

Fast Food Worst Customers factsWikimedia Commons

47. A Sudden Interruption

It was a Tuesday afternoon around 3:30. A regular customer calls and orders his regular pizza. This guy was always nice to me, but I could tell something was off because he had lost so much weight and started to get lesions on his forehead and hands as time went on. I get to his house around 4, maybe 4:15, and deliver the pizza.

I’m walking back to my car when I feel an iron grip on my shoulder and someone shouts “YOU GOTTA GET OUTTA THE WAY!” I turn and there’s four or five county sheriff’s deputies in full tactical gear. There were probably 15-20 officers in total. They lead me behind one of their cars and tell me not to move, then bust this guy’s door down and go.

I had to stay there for about an hour and had my car searched and everything. All that they found was a travel mug my mom gave me a while before I thought I had lost. Never took another delivery to that guy. I wonder about him sometimes. I never found out the actual reason behind the raid, but I have my suspicions.

Chilling StoriesPexels

48. I Have To Go Back!

I delivered pizzas back in '06. I had an older woman answer the door, take the food, and then invite me inside. To which I awkwardly said no thanks and went back to my car. Only after did I realize I left the machine with her. So, I had to go back and when she opened the door, she was wearing a VERY see-through nightgown.

It didn't leave anything to the imagination. She invited me inside again and I had to awkwardly grab the machine out of her hands and get out of there

Delivery Experiences FactsShutterstock

49. A Big Bite

I remember one time I was taking a delivery to a section eight apartment. I get to the door and the lady is immediately mad about her total and starts yelling at me. As I’m trying to explain why the total is the amount it is, I see her dog walk right behind her and take a massive dump on the floor. I decided not to say anything, hoping she’d step in it. What really happened was so much worse...

Well as I’m giving her the pizza, the dad sees what’s happening and starts chasing the dog away. Well along comes a kid around three years old. He sees a big ole chocolate bar on the floor... or so he thinks. As the lady is still rambling on and apologizing, this kid picks up this poop and takes a bite. With the most disgusted look on his face, he takes the bite out and hands it to his mom.

She started yelling at the kid and I dipped out really quick. One of the weirdest experiences I’ve ever had.

Delivery Service SurprisesShutterstock

50. Raising Brows

I am a Door Dash driver, and I'll never forget my weirdest drop-off experience. It was a couple pizzas from Little Caesar’s, and it was in a location I’d never been before. I get there, and it is this sketchy, rundown apartment building. It was dark outside and I was a single woman, so I was already on edge. The apartment I had to go to was in the basement of this building... Oh great.

So I get down there, and I knock on the door and I hear music from inside, death metal music. This guy opens the door and I can see into the dimly lit apartment, and seated on the ground is 5-6 people all sitting cross-legged in a circle, and they all of them turned to look at me when he opened the door. No one had eyebrows. None of them.

Not even the guy that opened the door had eyebrows. Needless to say, I swiftly gave him the pizzas and speed-walked back to my car. I don’t know what in the heck was going on in there, but I was not about to be part of it!

Delivery Service SurprisesShutterstock


Sources: ,

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