50 Times Deliveries Went Off The Rails In The Most Embarrassing Ways

Delivered 30 pizzas to an Amish family. About a 35 minute drive. The entire family met me outside to grab a pizza. I took the rest in and followed them inside to their dining table. The elder of the family gestured to me to sit down with them and he pointed to the one open seat. I realized that they saved me a seat to eat with them. I didn't know to much about the Amish back then, and I wasn't sure how rude it would be to say that in working and couldn't/shouldn't. I was also thinking on the other hand they could have killed me (remember I wasn't an educated 16 yr old) so I sat down and ate two slices of pepperoni pizza with them. I found the girl across the table to be very attractive. They said a prayer of some sort and didn't talk much after that. Just asked my name and how thankful they were for me to drive all that way. I finally had to get back to work. They didn't tip, which was fine. I enjoyed the time with them.

Edit: spelling.

This was in 2005? I think and it was for Pizza Hut in Fort Wayne, IN.

Edit 2: The curiousness of how they ordered. I don't know about all families, but I saw a lot of Amish heads-of-households (fathers typically) carry cell phones for "business" purposes. Besides farming, a lot of families made furniture for the clothes displays in stores and at malls and such. They had huge barns to make furniture. They would have huge generators behind the buildings to run the equipment. They can't be connected to city power and the generators couldn't run electricity for the house or lights, but the rules for the barn was different somehow. They aren't as disconnected as one may think. However their house was completely standard by Amish terms. Still had to heat up the bath old fashioned, there were flies all over, no fans, etc. I didn't see how they kept food cold if at all during the summer. No washer/dryer. But the generators sure did help with there business practices; running tools and such. They also don't drive, but they have vans and they would hire a non-Amish driver to take them to the city sometimes.

I delivered a pizza to a house, and a bunch of teenage girls open the door and started screaming and running around. Really f*****g weird but I gave them the pizza and left. Chalked it up to crazy high schoolers (I had just graduated highschool)

About 2 hours later I got a Instagram DM from a random person saying "A pizza wasn't the only hot thing on my doorstep this afternoon;)"

Turns out it was one of the girls from the house. I never gave them my name, but I eventually figured out that they figured it out from my god damn INITIALS. My first and last initials (which are very common). They must have gone through dozens of profiles looking for me

They invited me over for her 16th birthday party, and as soon as I heard that I just blocked the profile. I ain't goin to jail anytime soon. Nice ego stroke though.

Had a guy go to the door naked, I tried my hardest and never looked down, didn't say a word about it.

Worked in trucking, and we occasionally do personal deliveries to peoples houses. Anyway, we picked up a heavy as f**k crate from LAX to deliver it to some nice house in the hills. We were also supposed to un-crate the thing too. So we open it up and its a huge marble elephant statue that the owner bought from india. So for uncrating, we couldn't get the thing off the bottom part so there was this big feud with the logistics company and the owner. We waited at the ladies house all day, and she bought us pizza and sandwiches. A forklift had to come to help us move the elephant. At the end we got $50 tip from her. She was cool af.

I was a delivery boy for an Asian restaurant for a while. Had a delivery down a sketchy, very bumpy road in the back of my small town near all these trailers. When they answered the door, there was a 50-60 year old lady standing completely naked in front of me, as well as two men of the same age sitting on the couch with their dongs out, again, completely naked. I obviously got out of there as fast as possible, I took her signature and nearly ran away. She yelled at me through the window "Come inside with us!" And I said "F**k no" as I was walking away, and she proceeded to curse at me as I jogged back to my car.

It's interesting what kind of people you meet.

Was delivering pizza for a place in a college town that took orders until 4 am. Got assigned an order at 3:58 so I assumed it was going to be a colorful one.

Young shirtless guy opens the door and is absolutely covered in paint and blood. So are three other guys behind him along with everything else in the living room. They'd been shooting each other with paintball guns for what looked to be the entire evening.

He says, "if you give us the food for free I'll let you shoot me." I asked how many times I could shoot him to see what kind of value I'd be getting. It was something like $30 in food. We settled on five times. Best $30 I spent that year.

I was working at dominoz pizza place, I was told to deliver it to _____ avenue __nd street, only to find that it was a competitor pizza place, and I was cringing so bad when he picked up the pizza in the parking lot, he then started to head inside to eat DOMINOS PIZZA at the PIZZA HUT DINER TABLE. me and the cashier of Pizza hut stared at eachother for around a minute before I left.

Back in high school I used to deliver pizza and was working super bowl Sunday. Towards the beginning of the evening I got called to a house where there was clearly a viewing party. I rang the doorbell and their pit bull comes running up to the door. I'm not really afraid of dogs so I didn't think too much of it, but the first person to come to the door was a little girl super excited for the pizza. She ran up to the door and I could hear her dad yell "don't open the door the dog will get out!". But he yelled this right as she pulled ever so slightly down on the handle. From there the dog pushed through the rest of the way and I instinctively think, oh no I need to help them make sure the dog doesn't get out. Bad idea. The dog started attacking me, biting my hand first and then my shoe when I tried defending myself with my foot. Once the owner got to the door the dog took off and he let me inside. I was then surrounded by a bunch of strangers at this viewing party who seemed shocked by what happened. My hand was bleeding and out of shock I thought I might pass out. I guess the guys felt bad so he gave me a $20 as a tip? and I got out as quickly as I could after that. But at least I didn't drop the pizza.

Not a boy, but here's my delivery f**k up:

I'm a florist. One summer at the shop I was first trained in, I was to deliver an arrangement to a woman on her 92nd birthday because the delivery person was on his lunch. I'm terrible at directions and finding places, so it took me three times longer than it should have to even find the house.

Once I got there, I brought the arrangement to the door and rang the doorbell. The little old lady opened the door to which I respectfully (I thought I was being helpful) opened the storm door to be able to pass her her gift. Before I could even say, "Happy Birthday!" Her morbidly obese chihuahua comes bolting through the open doors past me, running around the damn neighborhood. The lady screamed, "Oh! You let him out! Oh no!" She was pissed! I was positive me letting that stupid dog out would give this decrepit woman a heart attack, so I went chasing after it. It took what was probably only five minutes to catch that obese creature (at least 10 lbs. huge for a chihuahua) and bring it back to her house, but it felt like forever.

I didn't even say anything to her. I closed the storm door and left, humiliated, about to have an anxiety attack. To this day I don't do deliveries.

I apologize in advance for formatting, I'm mobile and I don't post often. This was a few years back, but still crazy to me. Pulling up the house was already a bit strange since there were a lot of cars in the yard and neighbouring yards, and I was only delivering one pizza. I assumed there was a party and I was delivering to the chaperone or something. I was invited into the foyer by a lady, and I obliged (normally we don't go in houses, but I remembered overhearing something about special instructions). The lady asked me if I would take the pizza into the basement. Alarms immediately went off in my head. I politely tried to get out of that request, stating we were busy and making excuses. She persisted, politely, and said she'd tip me better, which just reinforced the alarms. I again politely refuse, and she gets a sad look and says "oh, well, the kids will be disappointed." Being the sap that I am, I asked what exactly was going on downstairs. She told me there was a youth group and I was just going to go downstairs to deliver a pizza to the speaker or something. I reluctantly agreed and headed into the basement.

I was expecting maybe a dozen littler kids, like 8-10 year olds. I get downstairs and the place was -packed- with teenagers. Probably 20-30 kids down there, all chattering and stuff, evidently waiting for me. When they finally noticed me, the room exploded with energy and everyone started chanting "pizza! pizza!" Thoroughly confused, I make my way to a guy with a microphone. He asks me my name, and I tell him, and the crowd starts chanting my name. The guy informs me that I had just won the Pizzalympics, hangs a medal around my neck (with a pizza picture taped on it) and a volleyball trophy that looked like a the person was serving a little pizza box. Crowd goes bananas again, I'm utterly confused, and make my way back upstairs as they keep cheering. The lady upstairs thanks me and I go back to the store, trophy and medal in hand (I still have the medal, the trophy got misplaced at the store sadly). Every time I tell the story, people think I was an absolute fool (I was) because it seemed like an obvious kidnap/r*pe trap (it wasn't, thankfully). Not sure I'll be able to top that one.

TL;DR: I got invited into a basement of a nice house, might have been kidnapped, got a trophy instead.

We had to deliver beer to a bar, and the delivery was standard with no weird hiccups or delays, but the girl accepting the delivery/ signing the invoice was crying the whole time, stifling sneezes and trying to hold back tears. It was something else trying to get delivery information from a girl crying. I think she even managed to cry on the invoice.

I was a delivery gal and delivered pizza. The most awkward encounter was a guy who answered the door in only a bath towel he was holding with one hand around his waist. He only had one hand to take the pizza and pay me. I was afraid he was going to let go of the towel while he was getting money to pay me.

I had just moved to France and my French was, shall we say… in its infancy. I was expecting a fridge to be delivered and when the phone rang I assumed it was the delivery van and it had got lost and needed directions. Most uk folk have difficulty in understanding a native French speaker until they learn enough to be able to make sense of the conversation. So what they do is simply ask lots of simple questions instead. Having missed his opening sentence I was doomed! In retrospect, what he actually said is that he was from a bike hire company based in a local village and would our holiday clients be interested? Having missed his first line, the conversation in French went like this. Are you lost? No I am at home! You should be at my house! Why? Because I need my fridge! Do you have a fridge? Yes, I have a fridge he said and laughed I need the fridge here with me! You cannot have my fridge it is in my kitchen. It should be in my kitchen I said He laughed a lot… you cannot have it, it is my fridge and I need it! I need it too!! I said Listen, he said… I am in your local village and have bicycles Bicycles? ?? I want a fridge! If I had wanted a bicycle I would have ordered one! Do you want to order a bicycle? He asked No!!! I want the fridge! Are you lost?? I persevered… The phone went clunk…

I was delivering pizza once in a pretty sketchy neighborhood and I came up to a gated apartment complex where I saw a dude waving me down. Sometimes customers in apartment complexes used to meet us outside if they knew their complex was complicated. So I'm thinking what a nice guy. :) turns out I was horribly wrong. I let this complete rando into my car who f*****g reeks of liquor and cigarettes. I somehow get the words out: uhhh hey man is this your pizza? This dude is barely coherent and responds with: no I need a ride. And I'm just freaking out at this point, wondering when the weapon or threats were gonna come out and I nervously respond with: dude I totally would but I can't I got pizzas to deliver look check it out. He keeps asking and asking and I just keep repeating myself saying if I wasn't working I'd totally help him out, I'm gonna get fired, etc. and after about 10 minutes the dude stumbles out of my car and went on his way. So freaky, lesson learned double check before letting drunk strangers in my car.

“How much did you pay for this house?” It was the first time we ordered dinner delivered to our house late one night. I listened for the knock at the door but the expected time came and went. I stood on the porch and watched a dark unmarked sedan drive slowly around the block twice in 10 min. (We live on the corner entering the neighborhood so It could have been anyone.) But the third time it stopped in front of our house. It was dark outside and I couldn’t see the driver. I thought I saw a paper map being unfolded. The car stayed there for 5 more minutes. I finally waved and a man came out, bag in hand. I expected him to say something about having a hard time finding the house, but instead: Delivery guy: Do you own your own house? Me: yes… Delivery guy: How much did you pay for this house? Me… (S eriously awkward.) I didn’t answer and handed him the tip. After he left I walked out to the street to look at our house in the dark. The brassy house numbers over the garage, so bright in the daytime, were basically invisible in the darkness, as were the black house numbers on our mailbox. Oops! We affixed a 3rd set of large house numbers next to the front door lamp the following day. But still! How much did you pay for this house?

I worked for a company call Waitr. Basically we were partnered with certain restaurants and we would deliver for them. It was my last drop of the night and when I got to the door something smelled rather musky. I knocked and I waited a few moments till the door opened. There stood a man with a massive bong and s****d beyond belief. It took me a couple of minutes to explain who I was and why I was giving him his food. He was friendly as could be. He even offered to share his food and w**d with me cause I was "such a sweet guy for coming all the way out here.".

I rang the doorbell and a woman about my age, twenty three at the time, opened the door. We were going through the usual exchange of pizza and money, when another woman who appeared to be her mother began walking towards us. "Well if you're not going to do it, I will" she said, while at the same time removing her shirt.
I was somewhat taken aback and must have looked confused while keeping eye contact with the young woman who was visibly embarrassed. "Don't be shy, you can look at them you know", the mother said. I glanced down at her b***s, then up to her face and gave a nod of approval. I looked back at the daughter, said thank you and walked back to my car. They tipped well too, so pretty decent delivery if I'm honest.

Delivered 200 smoke detectors (according to papers, never checked the goods) to another country. After driving for 20 hours trying to meet the ETA I arrived in a really shady looking warehouse, called the number on custom papers. A really strong built guy came outside, unloaded my van and asked me "how did it feel driving with a load worth 900 000 euros?" Not delivering s**t after that.

I delivered pizza to a house, the instructions said to open the gate and go into the backyard and knock on the back door. Now, I was really early. I showed up at their door probably about 12-15 minutes after they had placed the order as we were very slow. As i entered the back yard I heard really loud moaning coming from the open window and realized the customers were having sex. I'm not the one to ruin a good time, so I decided to wait until they finish before I knock on the door. I just stood there in their backyard with a pizza in my hand for a good 10 minutes. One of their nieghbors heard what was going on and saw me in there and decided to pop outside and just stand there staring at me the whole time making sure that i'm not stealing anything? Anyway, most awkward 10 minutes of my life.

Mine is tame compared to these, but

Literally my first day doing deliveries, punch the address into my phone and arrive as quickly as possible. Neighborhood is a bit shady but I don't judge.

Note on the door is really bad handwriting, but it says to knock because the doorbell is broken. Nothing unusual.

Guy opens the door: old, scruffy, skinny white guy. Says to come to the kitchen, that's where his cash is.
At that moment I realize I shouldn't enter a strangers house, but I didn't really have an excuse ready ("company policy says no" or something) so next thing I know I'm in his... living 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 thought I was gonna be murdered, but 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.