Many of us may not realize it, but delivery people are among the many unsung heroes of our world. After all, where would we be without the people who are willing to make the journey to wherever the calls come in from—just to make sure that we can all enjoy our food without having to put any effort into preparing it? If that isn’t convincing enough, perhaps learning about some of the crazy people, places, and things that these friends of ours often have to encounter along the way will do the trick. From the good to the bad to the ridiculous, here are 42 stories about some devoted delivery people’s most memorable experiences while on the job.
1. A Very Special Delivery
I once delivered a sofa to my own address, that my wife had apparently bought without consulting me on…
2. What’s Cooking?
I used to deliver pizzas in North Dakota and I always used to get some weirdos on a regular basis. Dirt roads were almost always a bad sign. One time, I arrived at the address in a trailer park, and there was a note on the door that said, “Please come inside, your money is on the counter.” Whatever, right? So I head in there, and there is a $20 bill sitting there for a $26 order. Great, so I decide to wait around for the rest.
After about five minutes, it was starting to look like a lost cause. I called the customer up to see what was going on, and a woman answered. I explained to her that she was a little short and she said, “Yeah I know, didn’t you see my note?” I told her that I did see the note, which is how I knew that she was $6 short. “No, no! The other note! The one on the microwave.”
Turning my head, I see a post-it note on the microwave with the words “Pawn Me” scribbled on it. “You…want me to pawn your microwave to make up the difference for your pizza bill?” “Yes,” she said, “we do it all the time! There’s a pawn shop right next door and they usually give me around $20 for it. That should cover the bill, plus a tip for your troubles!”
I wasn’t totally sure if this was legal, but I ventured over to the pawn shop next door—and sure enough, he did indeed give me $20 for their microwave. I asked if this was a common thing and the guy working the counter said that I was the fourth delivery guy that month to come in with that same microwave. Hey, at least I got a $14 tip out of it!
3. Pleasure Before Business
I arrived one time, pizzas in hand, at the door of a delivery for what turned out to be a college party. When the guy answered the door, he instantly recognized me from one of his classes. Without even realizing that I was there as a delivery guy, he immediately called out to the other guys that I was there—and that I had brought a pizza! Then, out of nowhere, three guys show up at the door, lift me over their shoulders, and throw me into the hot tub to join their party. I never made it back to work that night…
4. Identity Crisis
I’m a pizza delivery guy in college in central Pennsylvania. I am also of Asian background, which is an important detail for this story. I arrived at the front door of an older couple’s house one time with a large pie in hand. When I rang the doorbell, the woman came out. I said, “I have your delivery.” She looked at me with a puzzled expression on her face, and said, “We didn’t order no chinese food!” Of course, I had to explain that I was just the delivery guy and that what I had in hand was the pizza that they were expecting.
5. An Offer You Can Refuse
I used to work for Circuit City as one of the people who would deliver and set up TVs and computers.
There was this one time I’ll always remember where we were delivering a computer to this older lady who looked like she was in her 60s. When we arrived at her house, which was in the middle of nowhere, we could hear the loud music of the band Nine Inch Nails blasting from the window. We thought this must be an awesome old lady.
She then invites us inside and, while we are setting up her new computer, she turns off the music and begins to play lesbian-themed adult films on her gigantic television set right beside us—fully aware that we can obviously see this. We both just kind of ignore it and continue with setting up the computer in the most awkward silence possible. She then starts to talk to us about how she used to be an adult film star in her younger days, and about how she was into some really extreme stuff in the bedroom. She then asked if we would be interested in staying at her house a little longer after we finished the setup.
This was me, an 18-year-old kid, and my boss, a 40-year-old ex-marine. His response to her was simply, “Well, I’m married, ma’am, but I’m sure my young colleague here wouldn’t mind staying.” She then started hitting on me quite a bit harder. It got to the point where we just left in the most awkward silence of my entire life—that is, until my coworker and I got back to the truck and immediately started just laughing our heads off.
6. The Lion Sleeps Tonight
I’m a pizza delivery guy. I went to this one guy’s house and the door was left open with only the screen door in front of it. I rang the doorbell like three times and got no answer. I tried calling them twice or so, and I could hear the phone ringing from inside the house—their phone was actually on a table that I could view from the door.
So, I finally call a third time and this big fat pimply guy comes down the stairs in nothing but a leopard-colored speedo and walks over to pick up the phone. “Hello?” “Hello, this is the pizza delivery guy. I’m at your front door.” He just slowly turned his head, saw me looking at him, dropped the phone, and ran upstairs as fast as he could to change. When he did eventually come back down to grab his food and pay, I got a very generous tip!
7. Wrong Place, Wrong Time
I work at a shipping shop that ships UPS and FedEx. One of the UPS drivers once told me about a time when he was delivering a package. When he knocked on the door of the house, the guy inside yelled, “Come on in!” So, he opened the door and walked in on a couple having sex. Apparently, they had been expecting someone else. He assumed that they had been planning to partake in a threesome. Ever since then, whenever he knocks on a door, he always makes sure to follow up with “It’s UPS!”
8. Tangible Assets
I was once offered heroin as a tip for a pizza delivery. That was a memorable day on the job, to say the least…
9. Cold Case
I used to work for the cable company in Waterloo, Iowa. I went to a customer’s house once who, during the course of my installing their cable, tried to rob me. This was before I carried a concealed weapon as I do now, so all I had on me were some tools, none of which could defend against a knife to the throat. Being a broke cable guy, I gave him everything that I had—my lunch money and the checks from my last few installs.
When it was all said and done, I proceeded to leave and went immediately to the cops with the guy’s address, driver’s license number, and a check that he had given me for the security deposit on the cable box. The dude was obviously not very bright and was probably also high on meth at the time. Needless to say, he was caught pretty quickly.
10. A Series of Un-Porch-unate Events
I once had to make a delivery to a guy who was living under a porch. I drove up to the house. It was pitch black. No lights on. I look at the ticket and it says “use back door.” I go up the steps and still no lights on. Nothing. Then I hear a voice from below me say, “Hey, down here!” I look under the porch and, sure enough, there’s a small door leading into what looked like a makeshift apartment. I had to actually crouch down to get to it. I gave the guy his pizza and bounced the heck out of there.
11. The Key to a Man’s Heart Is Through His Stomach
I once delivered a pizza and the customer didn’t have any cash to offer as a tip. So, he decided to invite me inside for a beer and a slice of pizza to make up for it. That was a pretty awesome day!
12. Thinking Ahead
I once delivered a pizza to an older woman who told me to come in through the side door. The food was about $34, and she handed me what I thought was $40 and told me to keep the change. She was really sweet, asking me how I’m doing and all that while I was at the door. A couple of minutes later, I get back into my car and realize that it was actually $60 she had given me and that two of the 20s were sort of stuck together. I go back into her house to let her know, and she just says “Oh, I know! The rest is for gas and whatever else you might need.” I will always remember that lady because it was just such a random nice thing to do, and it really made my day.
13. Battle of the Sexes
I actually lost my job over this one, so here goes. I used to be a delivery driver for a Papa John’s on a college campus near the area I live in. One night, I got sent out on a delivery with a huge order, something like a dozen pizzas. They were to be delivered to a room on the fourth floor of a dorm on the opposite side of the campus. I got to the dorm’s main entrance and realized that this was a female only floor, but I went upstairs to deliver the pizza anyway.
For some stupid reason, I had apparently needed an escort since I was a dude. When I was caught being on the female floor without an escort, it quickly became this whole ordeal where the school administration and such got involved and I had to end up going to some hearing so that I wouldn’t get expelled. To make matters worse, they scheduled the hearing for the day that I was supposed to be leaving for a vacation. Oh well, live and learn I guess.
14. Man’s Worst Enemy
Once during a delivery, I had to kill a pitbull with a grappling hook from my ladder. I was doing a non-pay disconnect and some crazy dude tried to sic his dog on me while I was up on the pole. So, I took one of the hooks that attached to the hardline off with a wrench, and told the guy to put his dog inside or else I would disable it.
He told the dog “Sic him, boy!” So, I let the dog have it to the skull. One crack and the head was busted wide open. This was before cell phones or anything like that. The dude freaked out and couldn’t believe that I actually went through with my threat. I ran back to my truck and radioed to dispatch.
15. Turning on the Waterworks
A man once answered the door for a pizza delivery in a robe. The robe was closed, but I guess he wasn’t wearing any underwear because as we were exchanging money, a stream of pee just started to pour out between his legs and right onto his own carpet. He didn’t seem to even notice—either that, or he just didn’t care. I took a big step back out of the splash zone, and he just kept making small talk the whole time as if nothing was even happening.
16. Do My Eyes Deceive Me?
Back in my days as a young delivery guy, I pulled up to a small house one time that, at first glance, did not appear to be anything out of the ordinary. As I approached the porch, I could already begin to detect a pretty heavy odor of weed. I didn’t care, but as the two 15-year-old kids saw me walking towards them, they quickly scrambled the hell out of there like I was the fuzz or something.
When I eventually succeeded in getting over to them, they had managed to poorly hide their bong and we exchanged the pizza for the money. As I was leaving the scene, one of the kids suddenly stopped me, handed me a $5 bill, and said, “You didn’t see a thing.” I don’t know if that was the single weirdest delivery experience I’ve ever had per se, but it was definitely one of the most memorable and I found it funny as heck at the time!
17. The Back Story
I did not actually end up delivering the pizza in the case of my worst ever delivery because the address was an abandoned house. It was around dusk and the house was so obviously uninhabited. I could see trees growing through the windows and the back side of the house was crumbling so badly that I could see to the backyard—from the street.
The instructions were to “Come around the back.” I double checked the address after locking my car doors. I then called the customer a couple of times, called the store and told them what was up and why I wasn’t delivering the pizza, and headed out. I mean seriously! Who would have been dumb enough to go to the back of that house?
18. Sending Mixed Signals
This one always makes me laugh when I think back to it. I delivered pizza once to a house where an older guy walked out in a robe, just sort of mumbling to himself. I hand him the food, he hands me a 20. I tell him it actually costs $24. He mumbles ok and waddles back into the house. A few moments later, he comes back out and hands me another 20. I go to my pocket to get his change, but before I have the chance to he slams the door on me. Thanks, I guess?
19. Door to Door Service
I delivered pizza to a drug house a few times. It was always obvious that these guys were selling and using, but it never bothered me as they usually tipped well. Then one time, I got there and rang the bell. No one opened the door, and someone suddenly slipped a baggy of what appeared to be cocaine under the door. Not sure what to do, I decided to just kick it back under the door and leave. Not the worst thing that could have happened, but it definitely freaked me out and I still think about it a lot.
20. A Lovers’ Spat
One time, I delivered a pizza and the wife of the house answered the door and paid for it. Moments later, as I’m walking back to the car, her husband starts walking towards the house from the sidewalk. He stopped me and asked how much his wife had tipped, so I told him two bucks. He started muttering something about his wife being a cheapskate and then handed me a ten dollar bill. For those wondering, the bill for the order had been about $100. Thanks, generous stranger!
21. There’s Always a Logical Explanation
I was once delivering a pizza and after knocking on the door, I heard a faraway voice yell, “Coming!” so I waited. After about a minute, I hear the same voice, a little closer, yelling, “Almost there, just wait a minute!” This process continued for several minutes, with the voice coming closer and closer each time—until the person finally reaches the door and opens it.
Naturally, I’m expecting to see someone at eye level. Instead, I’m greeted by a smiling person on the floor who has no legs. They had dragged themselves all the way across the house to answer the door for me. I offered to put the pizza inside for them on the kitchen table, and they were pretty appreciative.
22. No Laughing Matter
I delivered about five pizzas to this guy once. I had to ring the doorbell several times before he came to get it. When he finally got there, he didn’t really say anything except to come on in real quick. Now, you generally aren’t supposed to go inside people’s houses for safety reasons—but I decided who cares, I can defend myself.
So, I get inside this guy’s huge house to find that it’s full of really weird things. There was a full suit of armor right by the door, and he had this Halloween-style CD playing creepy, deep voiced laughs from some other room. While he was searching for his wallet, the biggest dog I have ever seen just walks up to me and falls onto my feet, pushing me over. So, I’m now sitting next to a suit of armor petting this huge scary dog while waiting for this middle aged man to pay me. On the bright side, he gave me a $40 tip!
23. Not-So Secret Admirer
I delivered pizzas, and the shop that I worked for had a lot of “regulars.” It was a small town and we were one of only two shops of our kind. Anyway, I used to deliver to this one divorced lady’s house almost every week, and she used to flash me her private parts “by accident” all the time. She used to wear sweatshirts with really loose necks and always bend over in front of me, to the point where even a naive dope like me figured out that it was no accident!
24. Keep On Truckin’!
I once had some dude try to rob me in my van by jumping on the back of it during one of my deliveries. I have never driven that recklessly before, but he was hanging onto the ladder rack like something out of an action movie, so I had to try and shake him off. He eventually fell off somewhere on the interstate, and I didn’t see if he got hit by another motorist or not. I called 911, but they never found a body. Oh, and then I finished the rest of my route like a boss!
25. Expect the Unexpected
We ordered pizza once when I was having a party at my house, and one of my friends thought that it would be funny if he answered the door in his underwear. Upon opening the door, he was less-than-pleasantly surprised to discover that the delivery guy was his uncle…
26. Where There’s Smoke, There’s Fire
I was delivering a pizza to someone’s house who lived in a more rural area. When I got there, I noticed a kind of smokey smell, but I just thought nothing of it. I figured it could have just been from the pizza, although I didn’t really think it was. So, I roll up to the house, the guy answers his door, and I hand him his pizza. That’s when I notice that there’s a freaking bonfire in his living room!!
I think there must have been a large hole in his roof over the living room, because the smoke wasn’t pouring throughout the house. But I kid you not, this guy was just having a total burnout, burning books and wood and other stuff, in the middle of his house. I sort of just stood there gobsmacked. I had no idea what to say, so I just took his money and left. I definitely won’t be forgetting that one any time soon!
27. This Line Is Gonna Be Busy For a While…
This wasn’t me, but I recently heard a story about some customers who had called up a pizza place to make an order for delivery and had accidentally failed to fully hang up their phone when they were done. The delivery person then overheard their subsequent discussion, in which they went over a whole detailed plan of how they were going to rob the delivery person when he showed up. The delivery person immediately called the cops, who went in undercover as the delivery boy a few minutes later. The customers tried to beat up the cop and got arrested.
28. With a Little Help From a Friend
I used to deliver for a pizza place in the biggest city in Vermont. Many years ago, during a really bad snowstorm, I once had to make the trek out to the middle of nowhere to deliver a pizza to someone. I then had to stop about a mile out because a tractor-trailer had tipped over and was now blocking the road.
I called the customer up and told him what was going on and why I unfortunately didn’t think I would be able to get the pizza to him that night. He paused for a few seconds, then asked where I was and said he would be there in five minutes. Sure enough, five minutes later, a very very drunk man on a snowmobile pulled up beside me to claim the pizza. He also gave me a 100% tip.
29. Everybody Poops
While delivering a pizza, I once had to stand around and wait on the porch for close to ten minutes, because the customer had informed me over the phone that they were in the bathroom. I get that we’re all human, but that was still an experience I would have preferred to have avoided.
30. No Time for Small Talk…
I worked as a delivery driver for a very small Italian restaurant during my first semester of college. This one time, I delivered pizza to a very interesting kind of party. I brought the pizza to the door and casually said “having a party?” to the guy because he had ordered 12 pizzas. He answered by straight up telling me that he was hosting his first ever group sex party and that he was very nervous because he just wanted to be sure that everyone would have a good time. Talk about TMI…
31. Having a Bad Day
I used to deliver fried chicken. There was a big railroad depot in my town, so this one hotel operated pretty much solely on housing railroad workers who were in town overnight. There was this one guy in his fifties with a big pot belly who always looked unkempt and exhausted, who used to stay in the hotel regularly. One time, I had to deliver a pizza to him. He answered the door wearing nothing but his greasy looking tighty whities, with tears streaming down his face the entire time. It was a pretty awkward situation for me to be in, and I honestly felt more sad than anything after seeing that. Thankfully, he did at least tip well.
I was once tipped for a pizza delivery with a watermelon. No further questions.
33. Putting the “Fun” in Funeral
The most awkward experience I’ve ever had in my entire life was when someone ordered a bunch of pizzas to a funeral and I had to deliver them. I didn’t realize what kind of an event I was going to be showing up at until I walked in the door. There were A TON of people there, all somber and dressed in black, while I just casually rolled up in my bright red greasy T-shirt. I was definitely not prepared for any of the social interactions that followed!
34. Looks Can Be Deceiving
I arrived at a dorm building for a delivery one time and, like always, I pulled out my phone and checked the receipt for the name and phone number. The name on the receipt was Emily, yet a dude answered the intercom with a deep voice and everything. Thinking this was most likely her boyfriend, I go “Yeah, I have a delivery for Emily.”
The deep voice goes “This is Emily,” followed by a long silent pause. “Ok, well then could you meet me at the front door?” (which is common protocol for dorm deliveries). A minute or so later, I am met at the front door by an angry looking dude who is several inches taller than me with a five o’clock shadow, in a tiny yellow and pink dress, heels, and pink nail polish. Turns out someone had lost a bet. And badly…
35. Don’t Be a Pig
I once pulled up to this easily $1.5-2 million house. A lady opened the door and, as she was signing the receipt, I hear someone in the house shout: “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.
36. Just a Lazy Saturday Afternoon
I once had to deliver a pizza to a redneck hillbilly-type kid who was just sitting in the middle of his lawn on a hot summer day. He had his shirt off and was only wearing shorts with a super soaker on his lap. He ordered two pizzas, two liters of coke, and a side of breadsticks. He waved me over to him when I got out of the car and I told him the total, which was around $40. He handed me a $100 bill and I started to get him his change.
He then tells me not to bother, but I’m adamant that he surely doesn’t understand the amount that I would be keeping for myself here. He says he understands and I rebut by saying that his parents might care. He then looks back at the house, then back to me, and says, “Ah, forget about ’em!” I instantly realized that his giving me all this money was his deliberate way of getting back at his parents for not being awake at 2 pm on a beautiful Saturday afternoon in the summer to spend time with him. I took the money and thanked him.
37. Fight Night
I delivered pizza for many years. There was this regular customer who was a pretty good tipper, so we were always fighting over who would get to deliver to this guy. I got lucky one time and brought him his unusually large order. As it turned out, he was having a little get together and there were a bunch of seemingly excited dudes in his apartment. I saw a bunch of little glass bowls all around the kitchen and a couple more on the kitchen table. I then realized that all of the dudes were holding fistfuls of money and that the bowls were filled with beta fish. They were betting on fish fights.
I used to deliver pizzas back in high school. One night, a call came in from the town over from us for just a single large pizza. I packed up the pizza, drove over there, and noticed when I approached the house that there were cars lining up all along the entire street. It seemed like there was some kind of party going on, and that’s exactly what it turned out to be when I made it to the front door.
I knocked loudly and an attractive young girl answered the door, wearing nothing but her underwear. She then sprayed whipped cream all over her body and asked me to lick it off. Now remember, I’m just standing there with a pizza trying to make sense of all this. Before I know it, another guy from the party comes to the door and for some reason offers to give me a $10 tip if I accept her dare.
So I gave the guy the pizza, licked off all of that whipped cream, took my cash, said goodbye and she closed the door. And that, my friends, was the greatest delivery I have ever had.
39. Something Didn’t Seem Right…
I delivered pizzas for a bunch of different places. I have seen some weird stuff over the years, and even almost got robbed once. Luckily, I saw it coming and was able to get back to my car in time. Nevertheless, there is one incident that stands out in my mind above all the others. You get “regulars” like in any restaurant. People who order all the time, and who usually order the same thing. There was one delivery I would regularly make to a particular house, and a little girl of about ten years old would always answer the door and pay for the pizza. That wasn’t too weird—kids like to pay for pizzas a lot. The orders were sometimes early in the evening, sometimes late.
One evening, I delivered a pizza to her house, and she didn’t have enough money. I suggested that she go get one of her parents. She said that her mom wasn’t there and that her daddy “wasn’t alive anymore.” I asked when her mom might be back, thinking that she must have ran out somewhere, and the girl said “Thursday.” It was Monday.
I asked if she was sure, and she said yes. She explained that her mommy’s boyfriend lives in a nearby town, and that mommy leaves every Monday and comes back every Thursday, at least “most of the time.” I asked about grandma, any family, friends, etc. Her answer to all of these was nothing but no, no, no, and more no.
So, I sort of sat there wondering “Well, what in the world do I do now?” I thought about giving her the pizza and just saying, “Here you go, bye.” After one of those “probably only 10 seconds but feels like an eternity” moments, I asked her if I could borrow her phone. This was pre-cellphones, unless your name was Gordon Gekko. I called the police and sat on the steps with the little girl until they arrived.
She talked to me about her cat that had run away and about her little toy ponies. She even gave me a friendship bracelet! I noticed that her hair and clothes were dirty. I started to think about what it really meant for this poor girl to just be sitting in her house for days at a time completely alone. The police came, I told them my story, and they asked me to leave. I have no idea what ended up happening to the little girl. We never got another pizza order from that house again—and I would always check all of the orders whenever I worked, just to be sure. Whatever may have happened, I really hope that she is doing well now.
40. Flied Chicken
I was delivering chicken on behalf of KFC one time. When I knocked on the door at the address, I heard a kid yell “I GOT IT!” He opened the door, saw me, and immediately ran up the stairs yelling to his friends, “The chicken idiot is here! The chicken idiot is here!”—after which a crowd of about eight pre-teens at the top of the stairs began to throw a bunch of change down the staircase at me to pay for the delivery.
I asked if they could please hand me the money. They laughed and just started throwing the coins even harder. So, I picked up the bag of food and hurled it up the stairs right at them. It hit the wall, and I quickly split. I told my boss what had happened and said that if they called to complain, I wouldn’t listen or apologize—I would rather quit than have to deal with those guys again. I found out later that he did get a call, and that he told them to get stuffed. Good boss!
41. Taking the Good With the Bad
I am not usually a delivery guy, but one year I was doing some work for one of the major shipping companies. It was the Christmas season, which is their busiest time of year by far. One night, one of their delivery guys picked up his truck full of packages to start his shift, and there was some kind of problem with his paperwork.
He headed back into the shipping hub office to straighten it out, leaving his keys in the ignition like an idiot. He then came back out to find that the truck had been stolen. The kicker, though, was that many of the packages in the truck actually ended up being delivered to their appropriate destinations. I guess someone had just wanted to steal a parcel truck, but without being a Grinch!
42. Home Sweet Home
I used to have a gig doing on-site computer repairs for homes and businesses. Nothing fancy; usually just a matter of swapping out a part, proving functionality, documenting the call on my Blackberry, and then being on my way. So, I get a call this one time and head on over. The building is not in the best of shape, but it’s not exceedingly sketchy either. I get buzzed up to the customer’s unit and meet him at the door. He’s on crutches, has the worst teeth I’ve ever seen, and just looks kind of scummy overall. Amusingly, he was actually very polite.
Here is where things began to go south. He opened the door to let me inside, where I witnessed what was possibly the most heinous living arrangement I have ever seen in my life. His developmentally disabled girlfriend was just sitting there among piles of stacked newspapers, staring at me open-mouthed. Garbage bags filled with who-knows-what were scattered about and there were cockroaches literally everywhere. They were crawling up the walls. Over the sink. On the chair. In between the keys on the keyboard. It was a sight to see.
But, well, I had a job to do, so I started to get to it, all the while making polite conversation with the guy and ignoring all the vileness that surrounded me. The guy started to tell me his story. He was apparently hit by a car recently, hence the crutches. He was pretty polite, too: “Can I get you something to drink?” “Oh, no thank you.” “That’s quite all right.”, etc. Meanwhile, I can constantly see the ripples in the water bowl for the cats where the roaches are swimming. To them, it must be like a holiday resort or something.
To add insult to injury, I realized that the hard drive I was there to install had not been properly preloaded at the depot, so I had to wait there while Windows reloaded. I felt bad for the guy, as he was telling me that I was the nicest person he’d encountered in a while and that usually people just run away and refuse to help him. I finished the job, entered in the completion notes on my Blackberry, and got the hell out of there. At the next job, a roach fell out of my pocket. Lovely.
A few weeks later, my Blackberry goes off. I eyeball the address and it gives me the shivers, so I call dispatch to inquire about whether I’d ever been there before. The dispatcher takes a minute and then starts laughing. I asked why, to which he replied “It’s your completion notes. They read: ‘OH GOD, ROACHES EVERYWHERE!'” I had to fight my boss to not make me go there again.