31 Pizza Deliverers Share Their Most Awkward Delivery Experiences

The most awkward pizza delivery stories found on AskReddit.

1. This is what happens when you deliver pizza to a bachelor party.

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.

2. And this is what happens when a drunken man confuses the pizza delivery guy with a taxi.

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 with the passenger door open until the next hard right.

3. Delivered pizza to a man with a pretty strict wife.

Once, I was delivering pizza and when I got to the house a guy was hiding in the bushes of the home. He whispers to put the pizza at the bottom of the garbage can outside and then come over to the bushes so he could sign the receipt, etc. Apparently the guy didn’t want his wife to know that he had ordered pizza. He ordered regularly and this happened each time.

4. An exciting first delivery experience!

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 :)

5. May have delivered to a ghost.

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.

6. Delivered to a family in which the kid had better manners than the mother.

I’ve been delivering for 2 years, and surprisingly haven’t had any awkward situations, but there was this one little kid who answered the door, he was probably about 4,  for his mom. He brought the receipt to his mom to sign, and when he brought it back, he said “here, my mom doesn’t tip so I will!” and he gave me this crumpled up dollar from his pocket.

7. Stuck in the middle of a prank.

Girl answers the door, and yells to her sister, “your boyfriend’s here.” Sister comes running down in her bra and underwear. Gets to the door sees a confused looking pizza guy so she screams and runs away while yelling profanities at her sister.

The sister loses it laughing and gives me a $8 tip. Solid deliver 10/10 would deliver again.

8. This is what happens when you deliver to a guy who is passed out.

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.

9. An unfortunate delivery in which the customer was not aware of tax.

This one lady ordered a sandwich, which was just at the 6-dollar minimum for delivery. Total was 5.99 plus tax. Of course I come to the door and it’s an old lady. I tell her the price is 6.34 and she goes off on a tangent about how it was supposed to be 5.99.

I had to sit there an explain sales tax to her. She shut the door and came back with a calculator and I had to explain to her how to multiply by the tax rate and showed her why it was not 5.99 like her coupon said. Makes you wonder what she does at stores.

10. Naked lady customers are never fun either.

There is a woman in Stroud, UK, that will answer the door to us with genitals showing. Not a pretty sight and we all hate taking that delivery.

11. Sometimes you just feel like you’re interrupting.

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

12. A customer who wanted more than just his pizza.

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.

My manager insisted I make an effort to return the absurd tip but attempts to contact him the next couple days were unsuccessful.

13. Probably the least funny joke to ever play on a pizza delivery woman.

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 guy’s 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 are 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.

14. Two utterly scarring and sad female customers.

I can remember two customers that it was always awkward to deliver to. One was a lady so fat that she couldn’t breathe without making a rasping noise. Most of the time she was sleeping on the couch when I arrived, and sometimes I had to enter her house to wake her up because she was such a heavy sleeper. The worst part, though, was that she never wore anything more then her underwear. I avoided looking anywhere near her when I could.

The other was an old lady who was insane from drug use and was even more unattractive than the obese lady. She often had various younger men around and several times they were having sex when I got there. Whenever she didn’t have a man around she would invite me in. I don’t remember any specific conversations I had with her, but I remember she said some pretty crazy person stuff, and I felt really uncomfortable being anywhere near her. Luckily she stopped ordering pizza after a while because she owed my boss money.

15. Just don’t place a delivery as you’re getting arrested, okay?

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.

16. That time he witnessed pizza being placed on top of boobs.

It was homecoming night in Columbia, Missouri where the university of Missouri is located. I’m on a 2am run to an apartment complex that I often visit in my line of work. The order was an extra large cheese pizza. I arrive at my customer’s door and knock. No answer. I knock again. No answer. As I’m dialing the customer’s 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 neighbor’s chest and then hurls the rest of the pizza across the living room. To this day I wonder what that poor girl thought when she woke up the next day. And that, my friends, is my best pizza story.

17. Propositioned by a husband and a wife on two separate occasions.

I delivered to this house, rang the doorbell, knocked, and was about to give up, despite hearing the television. I decided to bang the door louder, and finally heard the customer yelling. He finally answered and insisted that I come in. This is against policy, just so ya know. I step in, and I see what looked like a soap opera on the largest television I had ever seen. Had to be 70 or 80 inches. Then BAM! Sex scene, gay porn, I was stunned. The guy was barely wearing tighty whiteys and started screaming and trying to explain about letting go while the wife was gone. I didn’t hear much as I ran out the door. He paid and apologized, and insisted that I go back in. I appreciated the tip, but didn’t go in. I just took the money and he already had the pizza, I left it when I ran. I had to go back the next week, and his wife was home alone. She let me know that she was alone, he was out of town, and propositioned me. I declined, another tip, and told the boss never again.

18. You know what they say: you’re never too old for pizza…

I was delivering food when this extremely weak sickly old man came to the door. He was so weak he had to lean on the door to stay up. After he paid he reached his weak shaking hand out, so I shook it. I shook his weak old hand and it felt like death. He was reaching for his food.

19. Greeted by a dumbfounded, staring child.

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.

20. A close call with would-be convicted MURDERERS.

I was nearly murdered. I was the driver at one of the places These guys called before they got someone willing to deliver and killed him. Franklin was just outside our range and we were about to close, so my boss left it up to me as to whether we would deliver as they said they would tip extra. If I were headed up that way I would have taken it, but there were friends waiting to drink beer with me so I wanted to get home (in the opposite direction) so I declined.

21. Whelp — he knocked on the wrong door.

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 policemen.

Turns out the apartment I was first knocking on was a girl that had been attacked by the town’s 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.

22. Delivered to prostitutes, met a friend.

Did delivery to the local hooker hotels around the restaurant I worked at in high school. Often the girl/women would answer the door naked and flirt etc with me. One young cute girl as far as I could tell lived in a room on the top floor and used another room for work. I delivered to her 2-3 times a week and one day she told me to come back after work and drink some beer and hang out. She told me about her life and man did it sound like shit, abusive step father raped then kicked her out, started doing heroin, kicked it, moved half way across the country to stay with family only to have more abuse. And here she was getting by but barely and was planning on moving South to Florida. We met up weekly for a few months and just talked. One day she said she was ready to go and that she wanted me to go with her. I told her I couldn’t, just started my junior year of high school and wanted to finish. We said goodbye later that night and I never saw her again.

23. A customer who couldn’t carry the pizza because she was apparently beaten so badly.

I used to work for Papa Johns in a not-that-great neighborhood of Chicago (Uptown, if anyone’s wondering). Anyway, I get to this woman’s house on my first week of driving and she answers, asking if I can come in to set the pizza down on the table. I politely inform her that it’s against company policy (I half thought it was a mystery shopper because we always get graded on delivery pepperoni pizza, which is what she ordered so I made sure not to go in). She then decides to tell me that she can’t hold the pizza because her boyfriend just beat her so badly that she was in the hospital. I look behind her and there’s a dude just standing there staring at me, no idea if it was the boyfriend but another girl appeared out of nowhere, took the pizza, handed me a tip and closed the door. I think I just stood outside the door for a good few minutes wondering if I should be telling anyone about this domestic violence confession.

24. Somehow found himself in the middle of an argument.

A horribly heated and evidently unplanned discussion about child support. When I showed up, with not only pizza but wings and an overpriced 2-liter, I was used as ammunition that she was not spending what he gave her wisely.

25. Probably best to not chill with the customers.

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 when 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.

26. This is what happens when you deliver to a drunk guy with not enough money.

Not exactly awkward — but this happened about a month or so ago: It’s about 3:30am (we’re open late as fuck) on a Friday night (Saturday morning, whatever fuck you) and I’m on my last delivery of the night. 2 larges, with a total of about 31 dollars. After knocking for about 2 minutes, this guy, shirtless, armed with some dry puke on his shoulder, stumbles to the door and opens it. Immediately, he starts tilting forward, like he’s going to blow chunks all over me. he turns it into a loogie, turns around, and spits it off the front porch, and starts reaching for the pizzas. “31 bucks, man” I say “Oh shit, right, I gotta pay you” he says. So, he disappears into the house for a good 5 minutes, I check Reddit, he comes back with a 20. he hands it to me, reaches for the pizza boxes again, and I say “31 bucks, man..” he says “can I just get one for the twenty bucks?” and I explain that I’ll have to call the store and ask them what they want me to do. He disappears into the house for yet another 5 minutes, only for him to stumble back to the door and yell “JUST TAKE IT” and slam the door. So, I made 20 bucks and got 2 free pizzas.

27. A really stellar move by the delivery guy, if you ask me.

Forgot a bottle of soft drink once… told them to give me a minute, jumped into my car, drove around the corner to the store, bought a bottle of soft drink, returned.

28. And this is what happens when you deliver pizza into the middle of a drug raid.

Late one night, a friend of mine had been kicked out of his house by his parents. Against the rules, but I let him ride with me until I got off from work. On one of my last deliveries for the evening, I was in an apartment complex with the worst building numbering system you could imagine. Made a wrong turn in the complex and had to turn around to go to the correct building. Upon pulling up to the building, a red sports car slid in sideways in front of my car. The driver’s door quickly opened and I was greeted by the sight of a man donned in black with a pistol pointed at my chest. I was a bit nervous at this point. I stood with arms raised, pizza balanced on one hand, bag of cash in the other. Luckily at this point, he identified himself as a police officer and showed me a badge. I had delivered pizza into the middle of a drug raid! I then had to explain why I had a passenger that did not work for the company and had no identification (it was still in his house). Good ending to this story though: my customers were arrested and in police custody, but the police officers bought the pizza for themselves, and since they had scared the piss out of an 18 year old kid who was “harboring a refugee” they gave me a $60 tip!

29. Delivered to customers whose dog had just died.

Their dog had just died. I got up to the sidewalk and noticed a woman sprawled out face up on the driveway just screaming and bawling. I thought, “okay maybe (hopefully) I have the wrong house” I looked around at the other houses not trying to be nosey. Can’t find any addresses and pretty sure I’m at the right place, I throw caution to the wind and ask this lady if she is all right. She gets up and composes herself and acts like nothing’s wrong, we walk to her door together and she pays and explains and says she’s embarrassed, I said no problem, I would think of her loss for her, etc. They open their delivery and we FUCKED UP THEIR ORDER. Like, hey sorry you’re having a bad day. Let me reassure you that your life is out to get you and that all food service guys are retarded. The man of the house at that point came and relieved her of her box, as she had just kind of gotten angry and started bawling again. The last view I had was of them hauling out a fluffy tail and two legs hanging out of either side of a roll of carpet and laying it in the trunk of their jeep.

30. Interrupted a pretty weird party.

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.

31. Delivered pizza to a naked man.

2 days ago a 40-something-year-old dude opened the door with nothing but a robe on with his shamalamadingdong hanging out. That was pretty awkward I guess, but he did tip me 5 euro which is nice.

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