Everyone knows that delivery guys are the unsung heroes of society, and their job can be pretty rough. But sometimes they encounter situations and characters so downright bizarre that they can never forget.
(Content edited for clarity).
A Surprise Visitor
“My boyfriend was delivering boxes of magazines to a small shop. It was really early in the morning, so the shop wasn’t open yet, but he’d leave them around back by the door. Rolls up, hops out of the van, grabs the box and takes it to the spot. He walks back to the van and there was a man sitting in the driver’s seat. It was dark and no one else was around, so he yells to him to get out of the van but didn’t approach.
Next thing he knows, the guy is out and running at him with something large and shiny in his hands. My boyfriend freaks out and runs, and the guy chases him. He doubled back around, jumped in the van, and took off right as the guy caught up and slammed the object into the windshield. It shattered but stayed in place so he couldn’t see anything, but he just drove out of there anyway.
Eventually, he pulled over when it was safe, only to find an axe was lodged in the window. A full-sized axe. He was shaking too much to drive after that so he flagged someone down to call the cops. They never found the guy.”
In His Happy Place
“Once I was delivering pizzas to a moderately affluent suburban home. Ring the doorbell of a house that was completely dark, expecting it to be a no-show. As I’m about to give up, a half-asleep older woman answers, says her husband must have ordered, and that’s he’s in back in the garage.
I make my way to the back, and sure enough the lights in the garage are on. I knock on the side door and he answers in a robe and pajama bottoms. He asks me to step in while he grabs the money.
The garage itself was decked out like a great retro man-cave, with a pool table and some pinball machines. But on the TV, there was this video. Young girls in school uniforms, riding a merry-go-round carousel, and REALLY enjoying themselves, shall we say. I tried to not-look-yet-look at this thing the entire time the dude was fumbling around for his cash.
Once he found it, he eventually paid me and gave me a $30 tip on a $20 pizza. Still so many unanswered questions about that.”
Yappy Yorkie
“I worked at a mom and pop pizza store. Once I was making a delivery to a house, and was greeted by a woman and her daughter (probably around 10 years old). I go through my spiel: ‘Hello, how are you? I have such and such order, is that correct? Okay, this is your total,’ and begin handing her the food.
She turns to her daughter and says, ‘Make sure the dog doesn’t…’ and can’t finish the sentence before the Yorkie goes tearing out the door. They start to panic (the street wasn’t busy, but it’s a small dog in a town where animals hit by traffic is a common sight, sadly), and I try to calm them down, saying that I’d be happy to retrieve the dog. They oblige, and after I hand them the rest of their order, I go after the dog.
This thing decides it’s going to go running four houses down. The houses aren’t too spread out, but I’m still chasing a dog in the middle of summer, wearing a black t-shirt in the dead of the afternoon. Anyway, I finally catch up to the dog, pick it up, and start carrying it back to the owners. After I hand the dog back and resume the business of them paying for the food, I’m rewarded with the princely sum of a $0.16 tip. So much for trying to go the extra mile.”
Have A Day
“I arrived at the address, and couldn’t help but notice the fact that there were six police cars parked at various spots along the street. Weird, but I’m in a semi-seedy neighborhood, and I’ve seen people getting arrested in the area a couple of times before. Get to the house (it’s more of a tenement) and the apartment I had to reach was around the back of the building.
I walk around the building, and it’s immediately clear that it’s a sketchy den of some sort. Grass hasn’t been cut in months, random, small items were strewn across the yard, apartment ‘numbers’ in blue painter’s tape on each door, you get the picture.
Get to the back of the building, and the door is wide open. I can still see the layout of the place: door opened into the kitchen, kitchen opened up on the left into the living room, small hallway heading back into bedrooms. A couch was situated in between the kitchen and the living room, and the TV was on, but there was nobody watching it. As far as I could see, there wasn’t anybody there.
Anyway, I called out, ‘Hello?’ and immediately a cop comes out from the hallway, looks at me holding up the pizza bag, and goes, ‘Gosh dangit, did you order pizza?’ I couldn’t see who he was talking to, but a voice from the living room goes, ‘Oh yeah, I did do that.’ So the cop walks around to the front of the couch and stands this guy up. Apparently, he’d been there the whole time, handcuffed and laying on the floor in between the couch and the television. Cop walks him over to the door, uncuffs him, says ‘Don’t try anything,’ and makes him sign for the pizza. Guy just looks at me and goes ‘turning out not to be such a good day for me, man.’
I have no idea what to say, and end up going with, ‘Uhh yeah, well, we all have bad days, man.’ Cop snorts and goes, ‘Guarantee you’ve never had a day as bad as this guy,’ and walks him back to the couch.
As I’m putting the receipts in my pocket and walking away, several other officers lead a few other people out of the back, all handcuffed. Guy gave me an $8 tip, which he definitely should’ve kept for bail money.”
Look Alive!
“I used to deliver Edible Arrangements. One time I was at a house in your average Northeastern suburban neighborhood and I had gone to the door with the arrangement but didn’t get an answer. So I go back to my truck, put the arrangement in the back side door, and was standing outside the open passenger door facing the truck, trying to call the customer to see if they’d be home soon so I can leave or if I should try to find one of their neighbors to take it in.
As the phone is ringing, the customer’s car pulls in the driveway, so I hang up the phone and wave. As they roll down their window I start to say, ‘Oh, hi! I have a delivery for you-‘ and the customer whose house this was just very calmly said, ‘I don’t want to alarm you, but there’s a bear right behind you.’
I turned around and not 3 feet away was a young bear (bigger than a cub, but not yet full grown) just sniffing around their bushes. I didn’t know what to do, my legs just turned to jelly and I froze. So I said to the customer ‘What do I do??’ and she looks at me like I’m crazy and goes ‘GET IN THE CAR.’
Now, the smart thing to do would have been to jump in the passenger seat that I was literally standing right outside with the door open, but in my nervous state, I slam the passenger door and run all the way around to get in the driver’s seat and lock the doors.
The side door to the refrigerated side of my truck was still open, but at least I was separated from the bear. The bear didn’t notice me until I slammed the door shut, but all he did was wander up to the side door and sniff the beautiful fruit arrangements in my truck. He hung out for a few minutes until the customer finally had enough and laid down on their horn until he took off running down the street. There were a few other interesting deliveries from that job, but none turned my legs to jelly like that bear.”
Nowhere To Run
“One night I have a delivery to a pretty rural area. A lot of my deliveries are to rural areas, so no big deal. But tonight it’s drizzling and especially dark, so I’m having trouble finding the address of the house I’m looking for. I roll down the passenger window and use my flashlight, pointing it at mailboxes/trees/posts/anything that somebody might have their address on at the end of their driveway.
I’m driving along at like five miles an hour pointing my flashlight when the beam catches a guy wearing a black hoodie at the end of a long gravel road staring directly at me. Whatever, could just be on the phone or something. Then it gets weirder. I finally find the address I’m looking for, pull into the drive, and hop out of the car. That’s when I get this sinking feeling. No cars, no house light, boarded up windows. If you’ve ever been a delivery person, you know that this is the time to bail because you’re about to get robbed.
Right as I’m about to jump in, throw the car into reverse and nope right out of there, I see a man walking across the empty field adjacent to the property towards me. Now I’m a pretty burly, bearded dude, so I don’t worry a whole lot on deliveries, but this scared the pants off of me. When he gets closer, I see him very obviously tucking something into his waistband, what I can only assume was a weapon. He then says in a thick, menacing southern accent, ‘I thought you was the law’ (I guess because of how I was scanning the addresses).
I meekly point to my car topper and the pizza in my hand, and he says in the nicest voice you’ve ever heard, ‘Oh, great! Thank you so much, have a great night!’ Pays me, and proceeds to walk back through the open field, in the direction of no buildings, in the rain, with his pizza. For the rest of my shift I couldn’t stop whispering, ‘What. The. Heck.'”
A Feline Fiasco
“A few years ago I delivered a large order with a few pizzas and several 2 liter cokes. It was the day after the Superbowl and the guy who answered the door must have partied too hard the night before because he’s standing there behind the glass door with a throw blanket wrapped around his waist holding it closed with one hand. In the living room, there were a couple of other guys sprawled out and it was obvious that they all were suffering from hangovers. He’s a young guy who isn’t hard on the eyes and I’m a red-blooded gal through and through so I was able to appreciate the view.
This guy opens the door, I tell him his total, which was $109. He hands me some money and then a big beautiful fluffy cat goes streaking out to freedom. This guy freaks out screaming, ‘Holy smokes my girlfriend will KILL me if I lose her cat!’ He drops the blanket and runs out after the cat and proceeds to chase it all across the lawn in the buff. I’m just standing there with pizzas on one arm watching the show.
He finally captures the cat and we make eye contact. Obviously embarrassed, he holds the screeching cat in front of his privates and walks quickly back to the door. As he’s going in, he says, ‘Just leave the pizzas on the porch table and I’ll get them in a minute. You can keep the change.’ Then he disappears inside. I put his food where he asked then went back to my car where I realize that he handed me two $100 dollar bills, leaving me with a $90 tip. Poor guy!”
More Than A Tip
“My car’s back right window doesn’t stay up. One fall, I was tired of stuffing things into the crevice to prevent it from falling because it eventually stopped working, so I duct taped it to oblivion. I started delivering soon after. One day I get to a house for a delivery, maybe 2 weeks into the job. My doors auto-lock when I start driving, so I formed the habit of unlocking the doors as soon as I open the driver door to get the pizza out of the back seat. This time, I guess I pressed the wrong button and locked the doors instead. I didn’t realize it until I had already closed my door and tried to open the back seat.
So here I am, in a customer’s driveway, their pizza in my back seat, locked out of my still running car. Two weeks ago, this wouldn’t have been a problem. I pop open my broken window, unlock the door, problem solved. Unfortunately, I’ve just duct taped the heck out of my window. Out of ideas, I knock on the door.
They answer, and I say something along the lines of, ‘Hey, I have your pizza but I’m really stupid and locked myself out of my car and your pizza is still in my back seat. Do you have a butter knife or something I can use to try to pry open my broken window?’
I hear laughing in the background. I’m ashamed. However, the mom of the house obliges and gets me a butter knife. I’m out there for a few minutes trying to open it to no success other than about an inch wide gap between at the top. I then see the mother and father coming outside. The guy brought me a JACKET because it was raining a little bit. He then tries his hand at prying open the window, also to no success. I see a light bulb go off in his head as he walks into his garage.
Apparently, this guy is a woodworker, and he just happened to have a slim piece of molding sitting around in his garage that he was able to shave to make it thin enough to fit through my window. He pokes it through the window and unlocks the door on the other side.
They get their pizza, and I get my car door opened again. I am SO grateful, and genuinely offer to pay for the pizza or at least half of it for their trouble. They refuse and still tip me 5 bucks. In all that craziness, I forgot to give them back their butter knife. I still have it to this day. Every time I see it, I remember that night and smile.”
Crazy Canine
“I pulled up to the house and there was a large German shepherd in the fenced-in yard going nuts, barking and snapping at me. It takes me about 5-10 minutes of grappling with this dog to make it to the door, and it runs around the side of the house.
So the folks open the door, pay for the food, and suddenly the dog bursts around the corner of the yard, slams past me and bolts into the house.
He’s sprinting in circles, freaking out and knocking stuff over including a nice looking lamp that broke. The people there start losing their minds trying to stop the dog from turning the whole house into rubble.
At one point, one of them turns and asks me, ‘Why the heck would you bring your dog with you on a delivery??’
It was an absolutely bonkers question, which let me know this was not their dog. I helped them get it out of the house, and they tipped me zero dollars.”
Send Him To The Loony Bin!
“I had a package addressed to an apartment building that didn’t have any door code, but one of those electronic key blip-thingies. Standard procedure when this occurs is to call the recipient, but there was no answer or voicemail when I called the number on the package. By standard procedure, I left the package with our tracing department at the terminal, and the next day there was a new number written on the package. Most trace workers just search the address or recipient and write down the number they find without test calling it first.
So, the next day I call the number in the morning and I get in touch with the guy whose name is on the package. He tells me it’s probably his roommate who ordered the package in his name, but we agreed to meet up outside his apartment at around 4 in the afternoon. All good!
A few hours later, I get a call on my work phone, and it is one angry dude on the other end. It’s the dude who I tried to call the day before, and boy, did I mess up his day. He proceeds to shout at me for 15 minutes about how he stayed home the entire day waiting for me, how incompetent I am, how I’m an idiot and should get fired and so on. He also claims to be the person whose name is on the package, which seemed weird to me since his roommate told me otherwise. I keep apologizing and offer to drive as soon as I can to his workplace and give him the package there, but he refuses. It all ends with him shouting at me to meet him at his apartment…ALONE.’
I’m a not very strong or scary girl, so I freak out about this as it sounded a lot like a threat, so I called my team leader and asked for help. He tells me to NOT deliver anything and to get the package to the terminal as soon as possible.
Turns out it was filled with illegal substances.”
A Serendipitous Snack
“Once I was delivering a pizza to a part of the city I wasn’t familiar with, and this was before smartphones and GPS were a thing so I was using a map. What I didn’t know was that the map was out of date, and the route I had planned was no longer connected, so the street was split into two for whatever reason. I ended up getting quite lost and drove around trying to find someone to ask for directions.
I see a group of guys in their 40’s hanging out on their back porch, and they asked me how much it was for the pizza when I inquired about my delivery. I was amazed at my good fortune, they paid, gave me a decent tip, and I headed back to the restaurant, only to be informed by my boss that the people who had ordered the pizza had called asking where the heck their order was.
Turns out these guys just happened to stumble upon a delivery guy with a pizza to deliver and felt they shouldn’t pass up on serendipity. Amazingly the original house still paid for their pizza after we remade it, but the restaurant never adjusted for the first pizza, so I got the full price of a large pie plus two tips from that one order. Cha-ching!”
The Majestic Man Cave
“It was a beautiful spring day, I was delivering about 40 bucks worth of sandwiches to a nice neighborhood in the early afternoon and was pretty stoked about the high probability of a good tip. As I suspected, I show up and the house is a real beaut. I walked up and hit the bell only to hear some guy yell from somewhere in the house, ‘Booya boys, food’s here!’
My first thought was: how did some frat boys have a house this nice? It was almost a mansion. Normally I wouldn’t let myself in, but I decided to roll with it. I walk through the front door and the entire house starts cheering, and its filled with dads. My mouth is hanging open as they proceed to take me downstairs to the ‘party palace,’ all the while I’m stepping over children’s toys. When I get downstairs, it’s the most beautiful thing I’ve ever seen–a next-level man cave.
They had a pool table, a bartender, and no less than eight TVs all streaming different games of March Madness. Before I can even say anything they’ve handed me a shot to take with them, and one of the dads says, ‘Here’s to you, brotha!’ I ended up hanging out with them for almost 40 minutes and had a brew while we watched the games and they explained that every year they take a week off from their firms and do this so they don’t miss a second of the March madness openings. When I tried to leave they kept asking me to stay and party, and I was pretty sure I would be fired, but they kept protesting that I stay. I finally get back to my store expecting to get canned, or at the very least a good tongue-lashing, only to find my manager slightly annoyed.
He said to me, ‘So, you met Mr. L, huh?’ I responded, ‘Who?’ and he said, ‘Mr. L called and said you would be running late, and that your dedication in the line of duty is commendable–he’s a pretty wild franchise owner.'”
One Miffed Mistress
“I’m working pizza delivery, my store get a call from a lady and my manager immediately groans and warns me about her as they’ve dealt with her for years. I think, ‘Okay, whatever, no big deal right?’
I get there and she’s a sassy, eyebrows-drawn-on diva looking lady. I hand her the pizza and she asks for the receipt, then says her ‘confirmation number’ (which doesn’t exist) wasn’t on the receipt. I tell her there’s no such thing, so she makes me call my manager. I do so and the manager talks to the lady and said he didn’t have her fabled confirmation number. So she hangs up and demands the pizza be free. At this point, it’s been 5 minutes and I have more deliveries and just want to leave.
Right then her husband has come outside, and I don’t care anymore so I just ask for my pen back. She legit won’t give it to me, so I try to non-aggressively grab it from the table next to her and walk out. She immediately snatches it up and stares me down like Medusa herself. Then her husband tries to grab the pen and she dodges him, and gives him a stare down that says, ‘You’re gonna pay for this later.’ I felt bad for him.
She then proceeds to chuck my pen into the parking lot. I was so mad that I just walked away, giving some rather rude gestures. Then she follows me to my car and gets my license plate number, calls my manager and tells him that I’m cursing at her and stuff.
When I get back to the store, my manager says they’ve been dealing with that lady for a long time and have given her countless free pizzas. The pizza joint doesn’t have a blacklisting system so she’d been taking advantage of it. Next day the owner shows me a review the lady sent to corporate about how terrible I was and how I should be fired. Luckily I wasn’t because they knew who she was, and I still don’t feel bad about flipping her a couple birds.”
That’s One Way to Get Your Pie!
“One day, I roll up to a house in a pretty rough part of town. I’m talking condemned red x’s on a third of the other buildings on the street.
I call the number, let them know I’m outside and walk up to the door. Someone calls out at me, ‘Yo!’ which I ignore–don’t go looking for stuff in the hood you aren’t involved with. But I hear it again, louder, and not from my left or right, so I look up.
There’s this overweight guy lowering a bag on a rope out of his second story window. ‘Yo, just put it in the bag,’
I instantly start laughing, check that the order is prepaid, and throw the food in the bag. I didn’t get a tip, but looking back to see this focused, determined man hauling his prize up…so worth it.”
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