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

This is probably not answering correctly but it was still weird. Delivered to this house and I noticed that they were in the garage so I went over to the garage door. They actually had a whole glass blowing operation in their garage and showed me the whole in and outs of he operation. They gave me a brand new bowl they had just blown and a good amount of w**d for a tip. Not weird like uncomfortable just different than the usual.

Was delivering to a neighborhood that typically was kind of sketch so I always expected no tip or a small one. I rolled up to this lady's house and she said something along the lines of "I don't have the money and my husband will be here in 20 minutes with some cash." It was the last delivery of the night so I wasn't worried about taking too long and then she opened up her garage door. There was a pool table and fridge and tv in there and she gave me a beer and we played pool until her husband came and gave me the money along with a $20 tip. One of the better nights working that job lol.

Sort of backward, I suppose, but I was a stripper for a little while in college. One time I was asked to show up dressed as a pizza guy. Got the wrong address. Some middle-aged women's wine and book party a floor below where I was supposed to be. They said they didn't order pizza, so I asked if they "ordered this" and started dancing and taking off my clothes. They freaked out and I was nearly arrested.

Pulled up to this easily $1.5-2mil house. Lady opens the door and as shes 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.

I was delivering a pizza and after I knocked on the door I heard a far away 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.

Was home alone waiting for my wife to come home. I decide good time to have shower well I’m there soaped up and hear the door bell quick rinse grab a towel head to the door thinking wife forgot her key. So I let the towel drop and open the door wrong there stood her mother. I don’t think I could have dived for the towel any faster. Her mom looked at me sighed and asked where Tina was I replied not home yet I’m expecting her any minute now. She hmphed and said I can see that. My wife walks up at that point and looks at me then at her mom and just started laughing. After that mom always phoned when she was on the way over to tell me to get dressed.

Delivered a pizza to a cryogenics lab on New Year's Eve. Pretty sure it was a prank-- name on the order said I. C. Weiner.

Mid to late fifty year old man comes to the door in an opened towel robe wearing Spider-Man undies.

Edit: This is a first of my comments to get any attention, so I didn't think to put more.

I was a Chinese food delivery girl back in high school.

This gentlemen opened the door very casually and honestly, I didn't think much of his undies.

What was really funny was from the other room I hear what I assumed to be his wife call out, "Is that Chinese or Pizza? Did I win?!"

The man saw the white plastic bag and sighed. "You won!"

As he was closing the door after giving a generous tip all I could hear was a celebratory woooh from the woman.

I had one, was the last delivery of the night at like 10:40 and the order was something like 23$ and change. The guy, clearly drunk, gave a 20 and what seemed like a bunch of 1$s. When I got back to the car, I counted the money and it turns out he gave me 162$. I ran back and had to explain to him what happened and after several minutes of him trying to process what happened, he eventually went back inside and gave me 33$ and thanked me.

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.

So 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 real quick.
Now you aren't supposed to go in people's houses but I decided who cares I can defend myself.
I get inside this guys huge house and its full of weird s**t. 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. So I'm sitting next to a suit of armor petting this huge a*s dog waiting for this middle aged man to pay me.

He gave me a $40 tip.

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. 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 phase me.

Side note: 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.

This is definitely one of the most memorable deliveries I had when I worked as a driver for this Japanese restaurant.

It was sent to this house with an order of a steak hibachi and a couple of sushi rolls that added up to something like $19.60. I liked to call before I got to a place, just to give people a bit of a head's up, so by the time I got to the door it was already open. In the doorway stood a chubby kid, about 9 or 10 years old that reminded me a lot of the kid from Bad Santa, but without the curly hair.

I tell him the total as I pass off his food. He hands me a $20 bill and with a straight face he smugly says, "Keep the change, pal." Immediately after, he closes the door and I stood there for a second trying to process what just happened. When I got back to my car I noticed the time and realized it was way too early for that kid to be home from school. I couldn't help but laugh at the whole situation.

No wonder he sounded a bit cocky when he told me that I could keep the $.40 in change. This kid probably faked being sick so he could stay from school and was probably in there watching TV or playing video games while eating sushi and feeling like a big shot. I know I would've at that age.

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.

I delivered pizza in NJ, I went on the porch to see a snarling Rottweiler behind the door. Not a big deal, happens a lot, I'm a stranger the dog is just being a dog. The lady pushes him back, we do the pizza transaction and as I'm turning to go the lady said, "Oh my god, he's out.. " the back door was open and the dog was charging around the house about to come on the porch.

I quickly opened the door to run inside but the lady screamed "no, the really bad one is inside" and I see a bigger Rottie just inside the hall so I stick myself between the screen door and the real door and I'm trapped in an angry dog sandwich. The outside dog bites my calf because I can only close the screen door so much, not much damage but I'm bleeding.

The manager goes to talk with the lady (it is like 1/8th of a mile from the store or that lazy b*****d wouldn't of bothered) and Rotties are penned up out back. As soon as the lady starts talking to him another small mutt dog zips out the door and bites him on the hand. He made the call on no more pizza for them.

I know of a kid who was a d**g a****t that had pizza delivered to his house. Once he heard the doorbell, he walked out his back door with a ski mask on and robbed the delivery driver in front of his own home. After that, he walked back around the home and opened the front door from inside pretending to be surprised that the guy was robbed.

Idiot ended up getting arrested but it was the worst plan ever hatched by someone I knew.

The other day we go at order at my store and the delivery said "If you can freestyle my order you get a $10 tip"

One of my driver's took the order over and the guy even played a beat for the freestyle. I'm not sure how it went, but my driver came back with a $15 tip.

The guy who answered the door looked like he had just seen a ghost and was a little jittery so I'm pretty sure he was on some kind of d***s.

Anyways, he hands me 10$ for a 15$ bill and tries to go back inside really quick. I realize that he didn't hand me enough money so I knock on the door and tell the guy he still owed me like 5 dollars so he starts patting his pockets and finally pulls his hand out to as if to give me more money but has nothing in his hand. He extended his hand to give me this imaginary money and was visually surprised when I wasn't fooled by his trickery.

The guy does this 2 or 3 more times before having me call my manager to attempt to use his card to pay even though I'm sure he knew it wouldnt work. At this point he goes back inside because he "just heard his roommate come in" and is going to "borrow money from him". So I wait, and I wait until I knock again. The guy cracks the door, sees its me, and closes the door again really quick like he was surprised I didnt go away.
Eventually after about 10 minutes of annoyance and feeling like I might get stabbed I told the guy I either needed money or the food, which he reluctantly gave back. All in all a very strange experience.

Strangest I had was a girl who put on her special instructions "Please tell me I'm pretty". I did. She smiled, said "thanks", closed the door and I never saw her again.

Maybe one day I'll get lucky.

I once delievered pizza to what seemed like a g**g house. I pulled up and there are all these intimidating dudes with tattoos and bandanas all wearing the same colored clothes. I puckered up and felt my s*****m shrivel as I awkwardly shuffled past them with a bunch of pizzas to ring the doorbell. They were all staring me down and it felt like the longest walk ever.

The person who ordered the pizza must have been the head honcho because he looked like the baddest of the bunch. The total was like $70 and he gave me a $100 bill and told me to keep the change. I bolted out of there and returned back to the pizza place on autopilot because I was so scared.