March 9, 2020 | Maria Cruz

Delivery Drivers Share The Strangest Thing They Saw On The Job 


Our homes are the only true place where we can really be ourselves. Sure, we can tidy up before the guests come over, but it’s an entirely different story with delivery drivers. Whether it’s offering them alternative kinds of payment or requesting mandolin lessons, these are some of the oddest things delivery drivers have seen on the job.

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#1 Big Tipper

I delivered a pizza to a young girl who was home alone. When she opened the door, her dog immediately ran away. I handed her the pizza, got in my car, found the dog and returned it. She left me no tip, so I was feeling kind of salty about it on the way back to the restaurant. A few hours later, her mother called the store asking to speak to me. 

She thanked me and explained they had left tip money but their daughter was so upset about the dog that she forgot to give it to me. I worked at this pizza place for two more years through college and they would get two large pepperoni pizzas and request me to deliver it every week after that. They always tipped me at least $25.

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#2 Flashy Jacket

I was delivering a pizza to a high rise once on a Saturday night. I got in the elevator and there was a guy dressed like a john who tried to buy the pizza I was about to deliver. He didn't even ask what kind or what size, he just pulled out a $100 bill and said, "I buy that for $100." I politely turned him down, so he pulled out another $100. I told him I could get fired. Man, that was hard to turn down. 

Here's where things get totally messed up, though. When I got to the door of the guy I am delivering it to, he opened the door and was also dressed like a john. I’m talking like a huge colorful jacket and everything. He grabbed the pizza, gave me a $100 bill and shut the door. The pizza was about $35, so I got a $65 tip.

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#3 Here’s My Money

Some dude once opened the apartment door completely bare. I was stunned but what came after that made me ask myself if he was some kind of magician. He put a hand behind his back and pulled a wallet. The only reasonable explanation I could give myself was that he tucked the wallet in a pretty disgusting place.

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#4 Don’t Tell Anyone

I was delivering a pizza to this house in a pretty rough neighborhood. These three guys answered the door and when the one guy stepped back to get the money, I noticed huge amounts of money and a lot of contraband. I was so scared. He gave me a tip of 20 dollars cash and told me not to tell anyone. Hopefully they aren't online.

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#5 No? Nothing?

I had someone answer the door once with a snake on his shoulders. Not like a milk snake or a garter, but a ball python (I’m no snake expert, though). It was probably about six feet long. I always laugh when I think about how when he closed the door, he told someone that I hadn't reacted at all. He sounded so disappointed. 

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#6 You’ll Have to Wait

There’s this one time that sticks out in my mind. Some guy ordered a large pepperoni pizza. When I got to the house, though, he wasn't anywhere. So, I called him because I didn’t know what was going on. He told me that he was in the bathroom taking a number two and I had to wait at least 18 minutes to get my pay.

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#7 Place Your Bets

I deliver for Doordash and Grubhub, sometimes pizzas. One time, I picked up an order from each app, same exact order, from the same restaurant, both named James, to the same hotel. When I knocked on the door , two guys were there and asked me which service I was from. I told them I was both and have both orders. 

They started to laugh really hard. When I asked what was so funny, they told me they had a bet on which one would come first. They thought it was going to be two different drivers and never thought one person would use both apps. I laughed too and asked them which one was James. They told me they were both named James. I still wonder what other funny things those two guys try to come up with.

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#8 Bro Halloween

Just simply coming up and there were three guys in underwear waiting for me. As I handed the pizza's over, more just started coming out in underwear and were also wearing cowboy hats. It was like some kind of Bro Halloween party or something. I had to grab my tip out of the dude’s bra. It was funny, but when I left the building I had to process what happened for a moment.

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#9 Women’s Clothing

There was this house where a young couple had ordered a pizza. I reached their place quite early and probably disturbed their session. The dude looked like he was partied out. So, when he answered the door, he had no idea that he put on his girl's skirt. It wasn’t strange, but it was very difficult not to laugh at.

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#10 You Have To See This

I delivered a pizza to this house one time. When I was standing on the front steps waiting for the guy to pay, I could hear all this hootin’ and hollerin’ from inside. The guy keeps looking back into the living room and laughing. After punching in his info, he handed the machine back to me and said, "Okay, you have to see this." He stepped back and I walked into the living room and saw five other dudes watching a strange adult video on a massive TV.

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#11 Grateful Cops

Back in college, I delivered to the local county jail. An officer was taking someone to jail one time. The guy going to jail, who still had his hands cuffed behind his back, got away from the officer and took off as I was walking in. He ran into me. The officer caught up to both of us on the ground and was able to subdue him. I was covered in pizza sauce. The officers took the pizza, paid and each gave me $20. I told my manager, we remade the order and I redelivered the order. The police were grateful and I was given another tip. One delivery made me about $400.

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#12 Mark’s House

I once delivered a pizza late at night. The person who took the call told me that the person who ordered (let's call him Mark) was an old man and may take a while to get to the door. I got to the house and all the lights were off, no car in the driveway. I rang the doorbell, but there was no answer. I knocked on the door, no answer. I called the person's phone, no answer. I called again, still nothing. 

At that point, I had waited for about 15 minutes for this person and was walking back to my car to leave. Suddenly, I heard the front door open, so I went back. Again, there weren’t any lights on so I could only see the head of a young woman peek from behind the door. She refused to open it all the way, though, even to take the pizza. I then heard another woman behind her say, "Who cares if he sees? Open the door." 

So, she opened it a little more to sign the receipt. She couldn't see, so I offered to shine my phone's flashlight so she could sign the receipt. I then realized that both of these women had no clothing. I averted my eyes as she signed the receipt and started walking back to my car. As I was walking away, one of the women yelled to me, "Have a good night, you know Mark is!" I burst into laughter as I had totally forgotten that this was the house of an elderly man.

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#13 Got Milk?

My father used to deliver Dominos into a wealthy area. He knocked on the door and heard shuffling around inside. This one guy opened it wearing a silk smoking jacket. There was a woman on the couch with nothing on. The guy handed my dad $100 for the one pizza order and said, "If you can go grab me a gallon of milk and bring it back, keep the change." They got their milk.

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#14 Public Pizza

A customer paid with a card and he had instructions to leave the pizza on a bench in a public area. I dropped it off but pulled on a side street where I could see the bench. I waited close to five minutes and then I saw a man bust out of a dilapidated building I thought was empty. He ran up, grabbed the pizza, spun a whole 360 degrees and glanced in every direction as if he was afraid of being watched. Then, he hurried back to the place. When he got to the door, he saw me and his eyes got huge. He slammed the door shut.

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#15 Ask for “Tim”

I live by a massive government facility in the DC area. This delivery was done at about 10:30 at night. I was told to ask for a Tim when I arrived at the back gate of the facility. I stopped at the gate and two black SUVs approached me. A man exited the second car and asked me what name he told me to ask for. 

I said "Tim,” gave him his pizza and got back in my car.  "Tim" then got back in his car on the passenger side. I turned around at the gate and left. The second car proceeded to follow me all the way back to the pizza shop. It then sat across the street for 15 minutes. They only drove away when I made a second delivery. That was my last delivery as a pizza guy.

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#16 As a Joke

Back when I was making this one delivery, I had two teenage girls open the door in their underwear. Hey did it as a joke I guess. They were probably 16 or something, though. I’m sure they thought it was funny, but I still had to report it to my manager. I hope that nothing came of it. I was about 20 at the time.

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#17 New Guy

I worked at a pizza place in high school. One of the delivery guys was a former army ranger. He was a blast and loved practical jokes. Well, we had a new delivery guy start one night and the ranger called and ordered a pizza. We thought it would be funny to play a joke on New Guy, so we asked the army ranger to “do something funny” to New Guy when he shows up.

New Guy went out and delivered the pizza to him (not knowing he also worked there). When he came back, he was very quiet and looked a little disturbed. I called up our friend and asked him what he did to New Guy. Army ranger answered the door wearing his girlfriend's lingerie and an army helmet. Not the sight a new driver is hoping to see I suspect.

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#18 Stay and Party

I was delivering to a trailer park and heard the strains of bad karaoke from the driveway. I knocked on the door and was greeted by a 50-something couple in their underwear who insisted I come in to set the food down and receive payment. The guy asked me to stay and party. I told him I couldn’t, my boss would be mad. He started doling out my tip in ones, with which he would beckon and retreat deeper into the trailer. His wife kept eyeing me and giggling. I ended it at three dollars. I just left as stoically as I could, then broke down laughing maniacally in my car.

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#19 Bound and Blindfolded 

I delivered to a hotel in the middle of a local golf course. I called the number to let them know I was there and was told to come on up. I got to the room and when the guy answered, there was a large group of guys, all in golf attire, surrounding a single guy in a chair. He was bound and blindfolded. The one that answered didn't even bat an eye, just asked how much and tipped me $30 bucks. Warily, I took the money and walked away, but before the door was fully closed, I heard one of the guys ask, "I wonder if he knows this is a…"

Before I even left the parking lot, the guy that answered the door called me to say that the bound guy was his brother. They said that he was bound and blindfolded because it was his bachelor party and the dancer was waiting to come out. Apparently, I just showed up to the hotel way earlier than they thought I would.

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#20 Agent of Chaos

A mate of mine was a pizza delivery boy during high school. He told me that he used to pull down driveways enroute when kids were outside playing. They'd freak out thinking that their mom and dad ordered pizza for dinner. He'd watch them lose it, then he'd just reverse out and drive off, breaking their little hearts. 

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#21 Keep the Change

The strangest thing was a woman ordering right next door. When she opened the door, she was wearing only a bra, had a huge fake chest, lip fillers, and platinum long hair. The order was about $20 and was already paid online. I told her it was already paid, however the lady took another $20 out of her bra and handed them over to me. She then winked and said, "keep the change." Needless to say, it made my day.

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#22 Still Remember It

I once delivered a pizza to the backdoor of a funeral home. Two guys in their 20s answered the door, both wearing long black rubber aprons over their shirts and ties. They also had on long black rubber gloves. The aprons were glistening with some fluid or other. Fortunately, the guy paying took off his gloves before pulling out his wallet and paying. I was only 18 at the time, but it kind of freaked me out. 42 years later, I still remember it.

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#23 Knock First

Strangest thing would be when I had to deliver pizza to my uncle (of course it had to be a family member). Me being me, I walked in his house without ringing the bell because he’s my uncle and I’m his favorite. When I went in, I caught him playing Halo 4 in his boxers and screaming at the TV. I died laughing and he nearly threw his remote at me. I learned to never walk in on him again.

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#24 Here’s Your Money, Bye

I showed up to a mansion in the rich part of the suburbs. The house was completely dark, so I called the number, but there was no answer. I got out and rang the doorbell three times. Still, there was no answer. I started banging on the door and called again with no answer. All of a sudden, the door flew open. Some guy in an open bathrobe, breathing all heavy and sweating, reached out, snagged the pizza, threw money at me, and shut the door.

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#25 Grandma’s House

I showed up to this massive house and a grandma showed up to the door. The first thing I smelled was a ton of the devil’s lettuce. This house not only smelled like it, but it was literally foggy inside. The grandma who opened the door was out of it, as was everyone else. They invited me inside for a second, gave me a fat tip and I left.

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#26 Taking Care of His Own

This guy would order boneless chicken wings, a two-litre diet Pepsi and cinnamon rolls every Friday. I can't remember the name on the order (I think it was Michelle). Well, a woman never answered the door and this guy gave us all the heebee jeebees. One day, I said, Oh. Why is Michelle always on the order?” Michelle was his cat. The cat would eat the chicken and he would eat the cinnamon rolls.

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#27 Two Pizzas

One time I, a retired Pizza hut driver, and a Papa John's driver were at an apartment at the same time. We both started walking up the stairs and after the third flight I asked her, "Are you going to 308?" We had a good laugh knowing we were going to the same place at the same time. The ladies at the apartment laughed pretty good when we were both standing there when they opened the door. One of the funniest moments I had while delivering!

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#28 She’s Single

One time I was delivering to this really nice house, almost like a mansion. The guy came waltzing out this big front door and was just all over the place. He attempted to give me the money but started babbling on about something I couldn’t understand. While he was scavenging around his pockets for the money, this one woman came out shouting, “Hey! What are you doing out here? Oh, what are we going to do with you?” 

She apologized for him and proceeded to pay. She also tipped pretty well. All the while, this guy got one last question in, “You like her? She’s single.” I was kind of taken aback as a 16-year-old kid just driving food around. It just threw me off. She then proceeded to scold him in a motherly way. “I am not single! This is my boyfriend’s house.” Nothing crazy, but I always thought it was funny nonetheless.

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#29 Just a Prank

When I was a teenager, my friends and I ordered pizza and prepared the house as if it was a dungeon. One of us was moaning loudly in the kitchen, the other was hitting the couch and yelling. Two were in their underwear, "playing" with a belt. The pizza guy couldn't open the door and left everything outside. He could never see our ruse.

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#30 His Own Man

We don’t deliver, but occasionally someone will order online thinking we do. We can’t do refunds in-store, so they have to ask head office. This one time, a guy did a big order and then realized what he’d done. He called us, asking if we could deliver it or cancel it. We said he couldn’t through us and he didn’t have enough to buy the order again, so he got a taxi to come pick it up. The guy basically delivered his own pizzas.

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#31 Play Me a Tune

One time while out for a delivery, I got to this weird house. A dude with no shirt on and scraggly curly hair held up a mandolin and just said, “Do you know how to play this thing?” I chuckled and said no. The dude slumped and looked down. He then yelled back to friends, “Man, this pizza guy doesn’t know either!” Another friend came to pay me and took the pizza. Not entirely crazy, but definitely memorable.

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#32 Into the Door

I had to do a delivery at this woman’s house one time. I knocked on the door and a moment later, a kid of probably eight or nine came screaming down the hall. He then face-planted into the door from the other side. His mom opened the door a few seconds later. The kid was smiling, but definitely red-faced as well.

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#33 Stopping for Gas

I delivered for a pizza place in the inner city near Chicago. I had to deliver for lots of house parties. I used to get invited inside a couple of times. I sometimes spent a good 15 minutes playing pong and partying with these people. I had more orders waiting at the store. When the general manager asked why I was late, I would say I had to stop for gas. 

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#34 Star Gazers

I received a call for two pepperoni pizzas one time. When I showed up to the house, there was an older-looking man and his dog on the roof. He didn’t say anything about being on the roof. I raised my voice to tell him I was the pizza guy and he just looked at me and then just jumped. It was only about 10 or 11 feet high, but it was kind of scary. He landed fine and gave me the money. I asked him about the dog and he said that there was always an open window so his dog could get on there and see the stars at night. I hope that man and his dog are doing well.

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#35 A Grand Time

We had an order for something like 15 bottles of water and no food, which was fair enough. I got up to the apartment and I heard some drum and bass music. The door opened and I was greeted by three people, all wide-eyed and looking like a group of barn owls. They were definitely doing something weird, but it looked like they were having a great time.

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#36 No Peeking

This one time, I made a simple delivery to a 30-day rent-a-room motel plaza. It was towards the far back of the plaza hidden among some trees. When the dude answered, I could slightly make out what I could only imagine was a lab in the back. He saw me glance at it and quickly adjusted the door so I couldn’t see past him. The delivery went normal and he proceeded to tip me $30 on a $14 order.

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#37 Super Delivery

Pizza delivery services are always open rain, shine, or blizzard. I was delivering pizza during a blizzard in Western Michigan. I was driving downtown on a main road when my car started spinning. I realized I hit a patch of ice and there was nothing I could do. I saw parked cars and electrical poles on both sides of the street. I was sure I was going to total my car. Instead, my car just kept spinning until I completed a full 360 degrees and kept on going in the direction I needed to go. The pizza was delivered!

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#38 Mr. Man

I was delivering a dessert and a drink one night. I knocked on the door and about 20 seconds later, the door creaked open and a kitty answered the door. It was like the door swung open and the kitty was just sitting there. I poked my head in and looked around and didn't see a soul. I was confused and even asked the kitty how he'd opened the door and how he was going to pay. 

Then, out of a back room, my colleague who worked at the same restaurant came out. I didn't know she lived there. I asked her if she opened the door, she said she didn't even hear the door as she was expecting a phone call instead of a door knock. She came out only after hearing a male voice, which was me talking to the cat. We still don't know to this day what happened. Mr. Man (the kitty) unfortunately took this secret to his grave.

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#39 Feeling Rejected

Years ago, I delivered pizza to an apartment every Thursday night. A very attractive woman would answer the door, usually without clothing. Usually, it was the same thing with her boyfriend. They acted as if it was perfectly normal and always tipped well. One time, I got there and they said that they didn’t have enough money for a tip. Instead, they asked if I wanted to spend some alone time with them. I declined, stating I had another pizza in the car to be delivered. I delivered there for another three months and still got good tips, but she wasn't as friendly. I guess she felt rejected.

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#40 Winning the Race

A previous co-worker of mine delivered pizza when he was in college. He told me that he once pulled up to a house and a group of high schoolers ran across the street with a finish line when he got there. They ordered from Pizza Hut and Dominoes at the same time. I don't remember which one he worked for, but he won the race.

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#41 Do You Like Them?

I worked as a driver and got a call from who sounded like a cute girl. She asked me to send my cutest delivery driver. I laughed and agreed (I was the only one on at the time, so it was me). I got to her place and she opened the door in a bikini with two friends behind her in bikinis. She asked if I liked them. I stumbled out a garbled “yes.” They all laughed and closed the door after paying. I never saw them again.

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#42 Still Wondering

I delivered to a motel. When I parked, I noticed a car with a high school parking pass and a kid inside giving himself a pep talk or something. Whatever. I went up to the room and two women in very transparent clothing opened the door, giggling. They were probably trying to get me to blush or something like that. 

I was going through a rough patch with a girl I liked, so this was really the last place my mind wanted to be. I was just trying to get money. I smiled at them and they tipped me fairly well. Nice! As I'm walking away from the room, they left the door open. I saw the kid getting off the elevator and heading into the hotel room. It was none of my business, so I just left. I always wondered how that dude’s night turned out.

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#43 On My Yard

During this one delivery I made, a guy came out and threatened me with a baseball bat and his dog. He said I was walking through his yard to get to the house I had to deliver to. I wasn’t. I was on the sidewalk. I've seen a lot of fun stuff delivering pizza, but that one guy freaking out was one of the wildest.

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#44 Better Than a Tip

There’s this one woman down the street from our pizza shop who’s a regular. Every other week, she’ll order a medium pizza with the same toppings. So, when I go for delivery and see that specific combo I already know who it is. She’s a super hot young woman who most likely lives alone or with a roommate because she’s always flirty when I deliver her pizza. Last week, I headed down the road to deliver her the usual. I got her phone number and we’re going out soon. It helps to be charismatic with any of your regulars.

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#45 No Bull

I remember one time when I was out delivering on a lone country road. I looked over to my left and there was a literal charging bull on the shoulder, keeping up with my car’s speed. He was running parallel to me. He had big ol’ longhorns on his head and everything. He kept up with me all the way until my next turn.

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#46 Pet Lizard

I once delivered a pizza to a guy and he invited me in to hang out with him. While sitting there, I noticed his pet lizard just chilling under a heat lamp. I commented on how cool it looked, so the guy tried giving it to me as my tip. I had to refuse as I wasn't sure what I'd do with a pet lizard for the remainder of my shift.

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#47 Where’s The Milk?

My location was in a gas station, so we would occasionally grab something for people as long as they tipped well and paid us back for what we got for them. There was this woman who we got milk for one time. She then proceeded to ask for milk every single time she ordered for years. Even though we kept telling her no, she would get mad when we showed up without milk.

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#48 Man in the Trees

I remember when I delivered to this house in the middle of nowhere. It was off this old highway that was rarely used. The house had a line of trees in front of it and right in front of the trees was the road. It was daytime, keep in mind. I parked on the side of the road to walk it up to his house since I couldn’t find a driveway. The guy literally jumped from behind the trees into the road, scaring me. He was some older dude, maybe in his early 50’s and had good intentions but… come on. There was no warning or anything. He just jumped out at me and gave me the money. He then said maybe two words I couldn’t even comprehend and disappeared behind the trees again.

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#49 It’s Just Johnny

I once delivered to Johnny Carson.  Around the mid-90s, Johnny was already in recluse mode by then. I was a struggling writer at the time and delivered pizzas at night. I got an order to a high rise and typically you just left it with the desk manager in the lobby and he would pay you. He had no idea about the pizza, so he told me to take it up. He used a key to get me in the elevator and up I went. 

The elevator opened up in a hallway and I knocked on the door. It seemed like I had surprised them because a pretty, middle-aged blond opened the door with a confused look on her face. Then, she saw the pizza and called back to the very fancy apartment. "Johnny, did you order a pizza?" Then Johnny Carson bounded into the room with an energy about him. He apologized and cracked a few jokes about getting old and forgetting to tell the guy downstairs. He then handed me a $50 bill. 

I told him I didn't carry that much change (it was less than a $10 order). He said, “Oh,” and pulled out a hundred. He told me to keep it. I said, "Thank you, Mr. Carson" and started to go back into the hallway. He said, "It's just Johnny, and you're welcome." He then patted me on the shoulder as I left. He was a very cool guy for the two minutes I saw him.

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#50 Good Answer

I delivered to a secluded house one night. A lady answered the door in a robe and asked, “If I flash you, will the food be for free?” I was dumbfounded, so I checked the receipt and it said, “paid for.” I said, “Um, it’s already paid for.” She said, “You’re honest” and then her boyfriend came to the door and tipped me a 20 saying, “Good answer.” Weird.

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