Delivered to an old lady smoking pot and listening to hendrix in her back yard. 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.

I deliver pizza, nothing too weird or anything where I live but I thought this one was funny. 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 shit” look on her face as she ran too. The mother then came back, paid, then I simply left.

I delivered a pizza to a guys house who was cleaning his gun while watching porn

My weird one is from several years ago delivering sandwiches in the downtown of a large city. There was a nice high rise apartment building next to the building our shop was in. A woman named “Cinnamon” started ordering to her penthouse apartment there almost every day, different sandwiches, but always with one of our giant pickles. She always answered the door in a robe with lingere clearly under it, and gave us exorbitant tips for literally going around the corner and up an elevator to make the delivery. The tips weren’t over $20, but it was substantial enough that when her order came in we would be like, “Who wants Cinnamon today!?” in order to keep things fair.

I delivered to an office with men playing poker with a topless (female) dealer

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.

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. She was nice enough but definitely had some mental issues going on. 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 wasnt she wouldnt order. She would only order if she knew that I was going to be the one to deliver her pizza.

I used to be a Chinese food driver in high school. This wasn’t your typical hole in the wall place, it was a pretty upscale place so I never had many problems or weird bits. One day that changed, to my surprise, for the better. Got a delivery to go to a hotel down the road. If you ask any delivery driver they will tell you that hotels are where the weird shit goes down. I get there and go up to the room which thinking back now may have not been the best idea but whatever, I was 17 and invincible.

Two guys open the door and their looks instantly scream meth heads. Prison tats all over them, torn up clothes, the whole thing. They ask me to come in and at this point my mind is saying run but I go inside. The room is disgusting; 10-12 Jack Daniels bottles all over, bed sheets everywhere, random papers, and about a pound of weed sitting right on the desk. That was the eye opener for me, literally a pound or more of weed just sitting there broken up ready to probably be sold. I thought i had witnessed something that I shouldn’t have and they would surely kill me and take my delivery money. To my surprise they pay for the meal and tell me to keep the change and I walk out with my heart racing.

I get to the car and realize I hadn’t counted the money and was sure it was going to be short and I would have to pick up the slack. Their meals together were $45.50 and they gave me… 5 $20 bills. Fuck yes. First week working and i got a tip over 100% from someone I thought would kill me. Super weird situation but it was the best tip I ever got.

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. tl;dr my mailman father kidnapped some little kid’s overly friendly dog.

I delivered pizza for ten years. Once I took a delivery to an average middle class home. The door was answered by a middle aged dwarf 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.”

When I was in college, I had a job where I took people their prescription medication each day (part of a program to keep the severely mentally ill out of hospitalization, because they needed their medication, but weren’t responsible enough to get more than a day or two at a time). I lived in rural Oklahoma, so a lot of the houses I went to were both pretty far out of city limits, and also pretty rough. One time, I had to take medication to this lady, who called in and told me that this afternoon, she wouldn’t be at her house, but instead she’d be at her dad’s. I got instructions on how to get there, and proceeded to drive WAY out of town down twisty little backwoods roads to find the place.

When I get there, her dad opens the door and goes “Hey! Come on in!!” I was young and stupid, but also 200+ lbs and a guy, so I went in. As I walk in, he shuts the door, and I realize that another guy had been standing behind the door, just holding a shotgun. I have a bad habit of talking too much when I’m nervous, so I immediately stuck my hand out to the guy with the gun and go “Hi sir, my name is Alex…” He looks at my hand and goes “Don’t you worry about who I am.” The patient came running out from a back bedroom, and took her medication. She thanked me and I left. I never went back to that house.

My strangest experience was delivering to this nasty trailer park. I pull up and the guy is outside waiting for me. (Bad news in bad neighborhoods, because it might not be that dudes house and he is planning on robbing me) anyways, I go up to him and he is high as fuck off something. 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 I’m a racist (he was black I’m white) he is cussing, and saying he will call the police. I then call the police… and he is promptly arrested for drug offences and counterfeit currency.