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9+ Times Delivery People Had Wacky Experiences on the Job

Photo Credit: Pexels

Everyone gets stuff delivered. Let’s just stop and think about that. EVERYONE gets stuff delivered. That means if you’re a delivery person, you’re gonna have to interact with some weird effing people – because even the weirdest effing people get stuff delivered. So, whether it’s your first shift or your thousandth, if you’re making deliveries, you are probably going to end up with a nutso story like these 14 we found on various AskReddit threads. Here’s hoping yours is just as entertaining:

1. That’s a nice tip!

I used to run a moving company in South Boston. We were a budget company, so most folks (in excess of 90%) did their own packing, and we just shlepped their stuff from point A to B.

One time this lady had a super heavy, refrigerator sized box (in excess of 100lbs by a good bit) that was just covered in duct tape and packing tape. As I got it through the doorframe, I caught it on something metal and the box ripped apart.

Out came no less than 347 dildos, one of which was about the dimensions of an average Boston fire hydrant, and another that was literally mounted to what appeared to be a small jackhammer, as well as a male sex doll and a disassembled Sybian.

I was moving her into a really nice house in West Newton. All she said was, “Please, don’t judge me.” I just said, “Do you happen to have any gloves? I’ll help you with this and we need not speak of it again.”

Thousand dollar tip at the end of that job.

2. A little too invested

I was delivering several pizzas to a house which came to a total of about $36. I walk up to the house knock on the door and a little kid answers the door. He hands me $40 takes the pizzas and closes the door. I stood there for a moment and just figured they were giving me the rest as a tip and the parents were too lazy to get off the couch.

I’m almost back at my car and I hear, “HEY PIZZA GUY GET BACK HERE!” I turn around and see a lady at the door in a towel. I walk back and she begins ranting about how I was trying to steal money from her kid! I explain to her that I just thought they were giving me the money as a tip, and if that was an issue, they can have it back. I gave her the $4 back and after talking a bit more, she ended up giving me $2 as a tip. Not that great, but better than having a ticked off customer. Thinking all was cool, I headed back to the shop.

When I get back at the shop, my friend who was managing the shop was on the phone looking a bit upset. He gets off the phone and explains that was the customer yelling at him about my behavior. I explain what happened.

Fast forward 20 minutes, and I have another order to take and I am putting more pizzas in my car. I go to leave but there is this big pickup truck in the way. I go to the driver and ask if they could move since I have pizzas to deliver. The driver responds, “Why so you could rip more people off!!??” I look closer and it’s the lady and her boyfriend! I go back into the shop and tell my buddy what’s going on.

My friend being the hilarious guy he is, grabs paper and a pen, and walks outside. He very obviously writes down the guy’s license plate, and heads back inside. Then proceeds to call the cops.

Shortly after that they took off. They tried to follow me most of the night, but found it hard in their oversized redneck truck and me in a little sporty pizza mobile.

3. Mistaken Identity

Posting for my dad, who is a mailman. Not exactly something that happened because of a weird recipient, but definitely an interesting situation. Dad’s delivering the mail, a guy walks up to him and says, “Hey, my dog’s missing. He’s a big white dog, very friendly, have you seen him?”

Dad says he hasn’t but will keep an eye out.

A few neighborhoods later this happy-go-lucky white dog comes bumbling up to the mail truck. Dad gives him a pat on the head and opens up the back of the truck for the dog, who immediately leaps in. Thinking he’s about to make this guy’s day, he rushes back to the original neighborhood, finds the guy with the missing dog and tells him the good news. He opens up the back of the truck only for the guy to give him a weird look and say, “Um…that’s not my dog.”

That’s when dad realizes that the neighborhood he took the dog from had a bunch of kids playing around in it, in the general direction the dog came from.

4. She likes you…

I used to deliver pizza. Every week we’d get an order from this lady that appeared to be living at a motel in the area. No matter what the weather was like she would always open the door wearing long sleeves, sweater, long pants and white cotton gloves. Apparently I was the only delivery guy that was nice to her though so she would start calling and asking if I was working that night and if I wasn’t she wouldn’t order. She would only order if she knew that I was going to be the one to deliver her pizza.

5. Not a good call, man

Attempted to deliver a pizza back in my delivery days to a guy who thought it’d be funny to scream, “GO AWAY!! I’VE GOT A GUN!!” after I rang the doorbell. So, I sprinted back to my car and left rivets in his gravel driveway while speeding out.

He proceeded to call the store and complain that I’d left. I told the GM what happened and she called the guy back and told him that he would not be allowed to ever order pizza again. On the bright side, I got free pizza that day.

6. What ARE you doing?

I deliver pizza. I took the delivery and this girl answered the door wearing only a towel, she looked like she just jumped out of the shower. She smiles at me a little flirtatiously, her towel is barely covering everything. Her mom turns the corner and yells, “WHAT ARE YOU DOING?” And chases her daughter upstairs. The girl got this hilarious “oh crap” look on her face as she ran too. The mother then came back, paid, then I simply left.

7. Oh, Jerry

I delivered pizza for ten years. Once the door was answered by a middle aged man who ripped the door open, screamed, “THERE’S NOBODY….(pause)…HOME!!!!” Then slammed the door in my face.

I stand there for about 45 seconds before a young woman answers the door and says, “Oh, hi. Sorry, that’s just Jerry,” then proceeds with the transaction like nothing is going on while Jerry marches around the house with his hands in the air screaming, “THERE’S NOBODY HOME. THERE’S NOBODY HOME. THERE’S NOBODY HOME.”

8. Monopoly Money

My strangest experience was delivering to a trailer park. I pull up and the guy is outside waiting for me.

I tell him his total and he hands me a “twenty.” Now this twenty was the size of monopoly money, was in a black and grey color scheme, and printed on obvious printer paper. You could also see where he messed up cutting it with scissors.

Now, I had no training on the matter, and apparently you are just supposed to take the money, and notify the store. But I was young and dumb so I told him there was no way I was taking that.

He gets pissed! He is screaming and saying he will call the police. I then call the police… and he is promptly arrested for drug offences and counterfeit currency.

9. Extra Cash

Delivered to an old lady smoking pot and listening to Hendrix in her backyard. She says she’ll give me a ten dollar tip if I take my shirt off. I just look at her and laugh. She says it again so I take it off and flex a bit to earn the money.

The lady grumbles, says it wasn’t worth $10 but gives it to me anyway.

10. Shut-In

I delivered pizza as a second job for a while. I had one regular Sunday night customer. He refused to leave the house or make physical contact so he had developed a system where I would place his pizza and soda on a platform and he would pull it up from his second floor window. I never actually saw him, just spoke to him on the phone. The order was always the same, a large Meat Lover’s pizza and a 2-litre bottle of Pepsi.

11. …what? 

On the receiving end of a pizza delivery…

After about 45 minutes of waiting for my pizza, I almost call the place when my doorbell rings. I open the door to a young man in his 20’s who looks kind of sweaty and nervous. I take the pizza and give him a $20 it was like a $16 pizza. He tells me he has no change, I tell him keep it. He leaves quickly. Lots of deliveries I figure.

My family starts eating the pizza when the phone rings. It’s the pizza place apologizing for the slow service and promises my pizza will be here in 15 minutes.

I let them know I just got my pizza, it’s all good. Then they tell me that their driver was robbed of his money and pizzas. The robber had delivered the pizza to me.

12. Extra Cash 2

I used to deliver pizzas in a very wealthy area of Dallas.

One delivery was for 5 large pizzas to a this really nice house. I walked in the kitchen and set the pizzas on the table. When I looked around I noticed there were a lot of older men and women dressed up, drinking, and there was kind of a strange vibe — it felt like a swingers party.

As I left, the host asked me what time I got off work, which was around 8pm, then asked if I would come back and strip for $200.

I said no.

13. “Two stoned guys and a dog”

The best delivery I ever had was to a medical marijuana dispensary in Colorado Springs when I was in school. They’d ordered over $80 of our most random menu items – desserts, appetizers, pastas. No pizza however. Anyway I get there expecting a huge party and it was just two stoned guys and a dog. They were so happy to see me and gave me the biggest tip I ever got!

14. Just drop it and go…

I delivered pizza for a few months when I was in college. It was a little town about 15 minutes from my university. I got a delivery one day to this old house that had been turned into apartments. I go to knock on the door and it is covered in weird signs (biohazard, no trespassing, caution, etc…). The guy answers the door and he is about 50 years old with long, messy, grey hair, wearing only a lab coat and the only light on in the apartment is a strobe light.

Guy: “Who are you?”

Me: “I’m here to deliver your food”

Guy: “Why should I believe that?”

Me: (confused) “Um, I’m holding it right here?”

Guy: “Fine, take your money. You should get out of here though, this place will be crawling with feds any minute.”

I got the heck out of there.

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