23 Pizza Deliverers Share Their Awkward Delivery Moments

Photo Credit: Pixabay

We’ve all had those minimum wage, part-time jobs that make us want to die a little. Most of those jobs involve working in retail or some sort of service industry – an industry that thrives on the idea that the customer is always right. These AskReddit pizza delivery stories will make you thankful your customer horror stories took place in the safety of the public eye rather than the privacy of your customer’s home.

#1. Hermits Need Pizza, Too

“Once had a delivery to a house that was in one of the rich neighborhoods. I pull up to the house, drive down a long-ass driveway, and when I finally get to the door, I see an envelope taped to it. There is nothing written on it except ‘Domino’s’ on one side, and ‘leave on doorstep’ on the other. Inside is enough money to cover the pizza and a $10 tip. I look around kind of awkwardly, before setting the pizzas on the doormat, and putting the money in my pocket. While I’m walking back to my car, I turn back around to look at the house, and lo and behold, the pizzas are no longer on the doormat. I didn’t hear a door, and it hadn’t been but 4 or 5 seconds since I had turned around. I also notice as I was getting back in my car, that there were cameras all around the perimeter of the house on the walls, painted the same color as the house to blend in. I drove away and not a single fuck was given.”

#2. Hey Dude, Nice Purse!

“My first day, first delivery ever. It was to a motel 6. The guy answered wearing red pumps, a purple and black kitty cat thong, and a pink felt blouse. Told him I liked his purse and walked out with a $20 tip.”

#3. Drunk Tippers Are the Best Tippers

“I showed up to deliver a pizza on a hot summer night and the guy who ordered it was passed out flat on his back in the living room just inside the screen door. The TV was blasting so loud he would have had a hard time hearing me knocking and shouting even if he hasn’t been unconscious. After about a minute he stirred, got himself up and paid. I think he intended to give me two tens and a one for the $18 pizza, but he was so out of it he gave me two twenties and a five, $27 tip.”

#4. Stripper Gram

“In my first month delivering pizzas as an awkward teenager in suburban San Diego, I pulled up to a house and got out, toting 5 pizzas to the door of a very unassuming house. As I approached the door, I could see someone turn off the lights to the front room and I got a bit scared. I had heard the stories of drivers getting jumped and robbed of their tip money so instantly my mind goes to that. I walk slowly to the door and ring the bell. After a few seconds I hear somebody behind the door ask, ‘How old are you?’ I answered, ‘Pizza Hut…’ Then I heard some muffled laughing. The woman again asks, ‘How OLD are you?’ Reluctantly, I answer, ‘eighteen?’ The door opens slowly and a woman is standing there completely naked with her hands outstretched. My jaw must have hit the ground. Then a flash of light from a camera behind her and a room full of guys bursts into laughter. Turns out it was a bachelor party. I got a good laugh but never did see the pic that was taken.”

#5. BDSM Sure Can Work Up An Appetite

“I once delivered to an apartment where two people in bath robes answered the door, I could see their bondage equipment and garments under their robes.”

#6. Are You Hitting on Me, or Am I Your Next Murder Victim?

“I was delivering 2 large pizzas to an apartment building one night. The recipient was waiting for me in the lobby. He was staggeringly drunk. Throughout the exchange he was vehemently trying to get me to come back up to his unit with him. I am not sure if he was gay or wanted to kill me and wear my skin, either way I refused. It took way longer than it should have to deliver 2 pizzas and when he finally got to paying, he just handed me $100 bill for the $30 order. He insisted I keep the change and may have winked at me as he said it. I am not positive on the wink though as he was so drunk his eyes were not totally coordinated.”

#7. …It Was One of the Most Terrifying Moments of My Life.

“Not so much awkward as scary but whatever. I’m a girl and when I was delivering pizzas I was around 18-19, pretty scrawny looking thing. Anyways, I had a big delivery to a guys party in his apartment. The apartment was on the top floor so after hauling about 10 pizzas up three flights of stairs I looked considerably frazzled. The guy opens the door and there’s about 15 men in the apartment and he says I should come in and put them down on the table. Now, I know better than to just enter people’s houses but this table was right near the door and there was no way I was going to be able to take the cash with three pizza bags draped over my arms so I take one step towards the table and hear the door slam shut behind me. He locks the door and says, ‘we got one’ and all these guys start snickering and although it turned out to be a joke (albeit, not a funny one) it was one of the most terrifying moments in my life.”

#8. Felon’s Gotta Eat

“I occasionally had to deliver to a motel 6. As I pulled in there were cop cars everywhere. Fuck me, don’t be the person who ordered pizza. Don’t be the person who ordered pizza. Fuck me it’s definitely the guy. We locked eyes. He was in cuffs, turns around says something to the cop. The cop grabs money off the dresser, I give him the pizza. Decent tip.”

#9. Keep It Classy, MIZZOU

“It was homecoming night in Columbia, Missouri where The University of Missouri is located. I’m a 2 am run to an apartment complex I often visit in my line of work. The order was an extra large cheese pizza. I arrive at my customers door and knock. No answer. I knock again. no answer. As I’m dialing the customers number her neighbor walks out of his place. He asks me if she was responding and I told him no. He told me that she often orders food and then passes out. He goes ahead and opens her door and to no surprise she is passed out face first on the couch with her boob hanging out. He asks me how she paid for it and I told him it was on her credit card. He signs the receipt and gives me a fat tip. He then proceeds to open the pizza box and takes a huge bite out of two slices of pizza. He plants the two slices on his neighbors chest and then hurls the rest of the pizza across the living room. To this day I wonder what that poor girl thought we she woke up the next day. And that my friends is my best pizza story.”

#10. That Time I Was Mistaken for a Serial Rapist

“I once went to an apartment complex, found the correct apartment number and knocked on the door but no answer. I could see a light on and saw someone moving around inside. I knocked several times but no answer. I went back out to my car to head back and realized I was at the wrong building. Oops… happens sometimes. So I walk over to the correct building and deliver the pizza. As I come around the building heading back to my car I am surrounded by police cars and police men. Turns out the apartment I was first knocking on was a girl that had been attacked by the towns serial rapist the night before. I felt so horrible. The police escorted me back to work and my boss had to verify that I was an employee and damn I was scared. But mostly I just felt so awful for that poor girl. I really had no idea and just fucked up to this day I’m really sorry for scaring that girl.”

#11. The Un-Ribbed Condoms Were on Sale, OK?

“I went to take an order to this one apartment and as I got to the door, I heard a guy yell, ‘ARE YOU FUCKING KIDDING ME? WHY DID YOU GET THE CAFFEINE-FREE COKE YOU KNOW I HATE IT!!?’ Immediately afterwards I heard a woman loudly say, ‘They were on sale, just like them unribbed condoms you got yesterday that you know I hate.’ I had to keep myself from bursting into laughter, so I ran down the hall to try and get it together and finish the delivery.”

#12. When the Little Kid Answers the Door and Just Stares at You…

“I’ve delivered pizzas for 8 years. I’ve seen it all. People fucking, people doing drugs, naked people, people arguing…you name it I’ve seen it. But to this day by far the most awkward thing for me is when the little kid answers the door and just stares at you. Just stares with those beady little kid eyes like they’re just looking deep into your soul. And then the parents finally realize that you have their dinner and then they have to look around for money for 5 minutes while this tiny little child is just giving you this stare down to end all stare downs, their eyes never wandering. The parents finally find the damn money and come to the door and they’re all like ‘Oh Johnny did you say hi to the nice man?’ And the stare continues.”

#13. Keep the Change, You Filthy Animal… IRL

“About a year or so ago Im delivering pizzas. I have an order somewhere up in the Hollywood area. As usual, Im blazing it on my drive over and blasting tunes on my 89 Civic’s bad ass stereo. I pull into a driveway and knock on the door. Who should answer but Macaulay Culkin himself! And he is high as fuck! I tell him it smells pretty dank in there. He invited me in, but I had like 2 more stops to go, so he offers me a toke first. Just then, Venus in Furs comes on my stereo, still blasting. So I says to him just before I spark up, I says, ‘dude, wouldnt it be hilarious if I got together some other pizza delivery drivers and started a band where we covered songs like this, but with pizza themes?’ He just said to me, ‘Man, you must be high’ Then we both laughed a lot. He paid me $50 for a $17 order and I went off to deliver the other two pizzas.”

#14. There Was Some Weird Shit Going on There…

“I walked up to the door and knocked and the guy who answered seemed pretty cool but… on the floor behind him was one guy passed out, from around the corner a blonde guy with long hair stepped out laughing like the joker with his shirt tied up like a bikini top and hair in a pig tail. there was a guy passed out on the couch by the door with a santa hat set up over his crotch awkwardly standing up from underneath. the transaction went through fine but there was some weird shit going on there.”

#15. Poor Lil Fella

“I was delivering to a house with an open garage. After a few tries at the door, I went around and knocked on the garage door–something you’re told never to do in delivery lest you be kidnapped and your kidneys sold on the black market. A man that looked like the stunt double for Sammy Hagar came out, beer in hand, and told me to step inside. I did. He took me through the house to the backyard where I spotted a hot tub with no less than two gorgeous women in it and a little person, resting his cast on the spa’s edge. I was offered a beer but declined as I was, ya know, driving, thanked them and went on my way. To this day, I don’t know how the lil fella hurt his hand, and to this day, I still wonder.”

#16. Ninja Pizza Man

“I had to fight a guy off after delivering a pizza. He was very drunk and thought I was a taxi so he kept on trying to get in my car. I literally kicked him out of the passenger side and sped off into the night passenger door open until the next hard right.”

#17. “New Girls Pay by Flashing Their Tits at the Pizza Guy”

“We had a regular delivery to a strip club manager. It was an early delivery and I always came in early so I got to know him and the regular girls after a while. One afternoon there was a new girl, the manger said ‘The new girl always pays for the pizza’. She looked a little awkward because it was early and didn’t have any money yet. I said, ‘It’s okay, new girls pay by flashing their tits at the pizza guy.’ She whipped them out with no hesitation. Manger paid me and we all had a laugh.”

#18. How Do You Know [Whatever His Name Was]?

“At the beginning it was not awkward at all. I got to the door. Young guy around my age answers. I was about to hand him his food and he asked if I wanted to come in and smoke a joint with his buddies. I said sure and walked in. Mind you, I didn’t have to wear a uniform for this job, so I was just in my regular clothes. We were sitting around smoking and eventually his buddies ask ‘how do you know (whatever his name was)?’ I said I didn’t and I was just there to deliver the food. Everyone just stared at me and I slowly walked out the door.”

#19. There Was Some Weird Shit Going on There…

“I walked up to the door and knocked and the guy who answered seemed pretty cool but… on the floor behind him was one guy passed out, from around the corner a blonde guy with long hair stepped out laughing like the joker with his shirt tied up like a bikini top and hair in a pig tail. there was a guy passed out on the couch by the door with a santa hat set up over his crotch awkwardly standing up from underneath. the transaction went through fine but there was some weird shit going on there.”

#20. Pizza Robbers

“This happened to my brother: He use to deliver for dominoes pizza and was 22 and was a pretty big guy, but was not prepared for this. He got an order in a ghetto/bad neighborhood and when he got there the door opened with a pistol in his face and three guys with bandanas over their faces. They took his money ($50), cell phone, and car keys, and pizza of course. Then they got in their car and drove off thankfully not hurting him. Mortified he started walking back to his work, luckily the robbers threw his keys out their car window down the road and he found them and walked back to his car where he had $150 more that they didn’t find. The police ended up finding the three morons because they still had the receipt from the pizza in their living room.”

#21. Stealing From Deaf People

“My most awkward experience delivering was when I delivered to this deaf woman. In the mist of trying to have her pay for her food I accidentally gave her the wrong change and left. I got back to the store and everyone starts talking about how I like to steal from deaf people. She had called the store furious right before I got there.”

#22. The Crazy Meth Head Lady

“I used to work at this place where we would always deliver to this meth head lady. She would hardly open her door to get her food/pay and one time she accused me of doing donuts in her neighbor’s yard when I had trouble finding her house. She also called the store every five minutes after placing her order to ask why it hadn’t arrived yet.”

#23. Revenge of the Poorly Tipped

“I used to deliver pizza about 15 years ago when I was in college. I used to hate it when I didn’t get a tip, so I kept a list of address that didn’t tip me. Those were usually the houses that had to wait an hour or so for their cold pizza. So, it was at the end of my semester and it was my last night delivering pizzas. The last delivery I had of the night was a house that hadn’t given me a tip all year. I was about to say fuck it and just take the pizza home with me, but instead, I took a bite out of one slice and delivered it. I was less than a block away when the boss called me telling me to give them their money back.”

We know you can choose a lot of sites to read, but we want you to know that we’re thankful you chose Did You Know.

You rock! Thanks for reading!