'There's a bear right behind you': 10+ Delivery drivers share their craziest delivery experiences ever

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Jun 10, 2024 11:00 AM EDT

Delivery drivers have seen it all. Really and truly, they've found themselves involved in the craziest situations imaginable!

People order delivery for all sorts of reasons. They might just want food, but they also might be in the middle of a stressful move, or trying to watch a handful of kids, or they might be some college kids who are partying. The delivery drivers never know what type of scene they're going to be walking into when they show up with food in hand. More than 2,800 people answered u/XerxesJester's question: "Delivery drivers of Reddit, what have you experienced on a delivery that you will never forget?" 

We picked out some of the most funny and shocking replies. Interestingly, a lot of people who shared their stories either delivered pizzas or sandwiches. Some of them encountered rouge dogs, which must be a constant problem for the delivery workers of the world. Lots of dogs love to race out the front door at any chance they can get. One person even shared that when that happened to them, they ran after the dog and caught it! Scroll down to read what happened next, as well as a bunch of other great anecdotes. 

Up next, read the update to this school worker's saga: they were hired for marketing, but their boss continually tried to make them be a substitute teacher instead! 

Add as a preferred
source on Google
Advertisement
  • 01
    Cheezburger Image 10358546176
    via Paolo Feser on Unsplash
  • 02
    Delivery drivers of Reddit, what have you experienced on a delivery that you will never forget?
    via u/XerxesJester
  • 03
    Silly Silhouettes In near hurricane conditions I was delivering subs for Jimmy Johns. Took me a little longer than usual to get to a house, I am completely drenched, standing in the rain because the front door didn't have a stoop. The guy opens the door and says "took you long enough" grabbed his sandwich and didn't tip me.
    via u/Silly Silhouettes
  • 04
    Winnifred Thadeo... 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
    via u/WinnifredThadeousP**
  • 05
    to call the customer to see if they'd be home soon and I can leave or if I should try to find one of their neighbors to take it in. As the phone is ringing, the customers car pulls in the driveway and so I hang up the phone and wave, and as they roll down their window I start to say "Oh, hi! I have a delivery for you-" and the customer who's house this was just very calmly said "I
    via u/WinnifredThadeousP**
  • 06
    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
    via u/WinnifredThadeousP**
  • 07
    crazy and goes "GET IN THE CAR" Now, the smart thing to do would have been to jump into the passenger seat that I was literally standing right outside with the door open and everything but in my nervous state, I slam the passenger door and run all the way around (the long way around the truck, too smh) and get in the driver's seat and lock the doors.
    via u/WinnifredThadeousP**
  • 08
    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
    via u/WinnifredThadeousP**
  • 09
    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.
    via u/WinnifredThadeousP**
  • 10
    Dylan Bob1991 I pulled up to the house and there was a large German shepherd in the yard (which was fenced in) going nuts, barking and snapping at me. It takes me about 5 to 10 minutes of grappling with this dog to make it to the door, and it runs around the side of the house.
    via u/Dylan Bob1991
  • 11
    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.
    via u/Dylan Bob1991
  • 12
    The one dude asks me "why the would you bring your dog with you on a delivery?" Which was an absolutely bonkers question that let me know this was not their dog. I helped them get it out of the house and they tipped. me zero dollars.
    via u/Dylan Bob1991
  • 13
    TrailMomKat When I was about 6 months pregnant with my first son, I delivered for Papa John's in an area that was mostly not so great. Now, that area has the highest violent crime rate on average or something or other for our state, so that should tell you how bad it was about 10 years ago before it got downright awful.
    via u/TrailMomKat
  • 14
    Well, one neighborhood in particular was the worst of the worst, and usually another driver would take it since I was pregnant, but that Friday night we were short and super busy, so I did it without hesitation. Gotta eat after all, right? So, I get there, get out of my truck with the pizza, and get a really, REALLY bad feeling. Quickly look around, and
    via u/TrailMomKat
  • 15
    see a group of guys watching me. I put on my war face more or less, and as a second thought, stuck my big belly out a bit so it'd be way more obvious in the dark. One of them approached me and was like, "oh, you pregnant?" I just shrugged and said "yeah... that definitely ain't a basketball, dude." He chuckled at that,
    via u/TrailMomKat
  • 16
    walked back to his friends, and I heard him say, "naw, yall, come on, she's pregnant." They all walked away and the dude that I'd spoken to gave me a nod and smile, told me to take care. Found out later that one driver had been brutally beaten in that lot less than a couple
    via u/TrailMomKat
  • 17
    months before I'd been hired, and if I hadn't been pregnant, I might've suffered the same or worse. Glad that didn't happen.
    via u/TrailMomKat
  • 18
    tangoewhisky Shared this on r/talesfromthepizzaguy, so I'll share it again. I worked at a mom and pop pizza store. I was called up for a delivery, bagged the order, entered the address into my GPS, and set off. After about twelve minutes or so, I arrived. I walked up to the door, knocked, and was greeted by a woman
    via u/tangoewhisky
  • 19
    and her daughter (probably around 10). I go through my schpiel: "Hello, how are you? I have $Order, is that correct? Okay, total is $Amount," and begin handing her the food. She turns to her daughter and says to her, "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
    via u/tangoewhisky
  • 20
    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.
    via u/tangoewhisky
  • 21
    The houses aren't too spread out, but it's still me 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. I hand the dog back to them, get back to the business of them paying for the food, and I am rewarded with the princely sum of a $0.16 tip.
    via u/tangoewhisky
  • 22
    You are reading that correctly. 16 cents for returning a Yorkie.
    via u/tangoewhisky
  • 23
    plutonn I met a nice puppy when i was delivering to a farm.
    via u/plutonn
  • 24
    omza I occasionally pick up delivery routes at the supermarket I work at part time, and the range of customers is crazy. The city has two universities (loads of students), and a -load of elderly and highly self- entitled (not mutually- exclusive) customers. The system we use for deliveries/sat-nav. shows us
    via u/omza
  • 25
    "Customer Comments" right before each delivery, usually consisting of instructions. like "There is a lift to the right as you enter". Additionally, we are a fairly small branch, and so the comparatively smaller line we stock is made known to customers when ordering. If you don't want items to be substituted if unavailable, you mark it as so when ordering (not a hidden
    via u/omza
  • 26
    button). The other week, this lady had put a note to give her a call 45 minutes before I arrived... as if she was the only customer to whom I was delivering. The note went on to tell me "not to even bother bringing any substitutions as she does not want them". I immediately knew this was going to be an issue, as I
    via u/omza
  • 27
    could see there was about 6/7 crates for this customer. I was only a 10-minute drive away, so called and apologised that I couldn't do so sooner. She said it was fine, and that she would be waiting outside to meet me, describing how I could identify her upon my arrival as "the two unmistakeable ladies". It turned out to be a mother and daughter, and
    via u/omza
  • 28
    the order was a food shop for the daughter at uni. which the mother had placed. Without any cue, the daughter began going through the crates removing items saying "not this, not this, that isn't organic, this is cruel, that has oil in it, definitely not that... omg why did you order those?!" like an ungrateful little something. She also berated her mother for not ordering
    via u/omza
  • 29
    certain things, and got stroppy when she didn't find certain other items right away. The mother said "oh I'm sure the man will be able to get you this" as if I had the entire stock of the shop in the back of my van. When I explained I couldn't do this, she began pointing at other crates saying "but you have this there?!" (a different customer's order).
    via u/
  • 30
    The mother begins to tell me how she's never shopped online before, and her daughter has a very strict, doctor-ordered diet; whether she did or didn't isn't really my concern, but it certainly came across as the daughter having other reasons. Again, it's not my concern, but she shouldn't have gotten her mother to order, and perhaps should have shopped from
    via u/omza
  • 31
    somewhere which catered to her needs more. When I also explained that I can't just give her other items from the van, she said "but every other time I've ordered they've done so- and-so?!" first order, sure... - Now the real part that I me off is how the daughter had pulled things. from the crates; on my
    via u/omza
  • 32
    system, I have to find each item individually from each. crate number, and then manually remove them. Which means I have to know which crate they were in originally, since usually it's only one or two items that get sent back. A lot of the items were fresh as well (from the meat/fish- counters) meaning they had to be binned.
    via u/omza
  • 33
    Anyway, they got impatient, angry, and unreasonable, and I was late to all the remainder of my drops. That's only one of many stories...
    via u/omza
  • 34
    aboughtcusto Not me but my dad was a fedex delivery driver. One place he was knocking at the door waiting for an answer and then begins hearing heavy breathing behind him. Slowly he turnes around to see a ostrich staring at him.
    via u/aboughtcusto
  • 35
    Second one, he made a delivery to this mans country farmhouse. As you walk to the house you can clearly see into the barn. As he was approaching he saw bodies hanging from the scaffolds. Turns out the guy was big into doing special effects for movies and helped with silence of the lambs.
    via u/aboughtcusto
  • 36
    DaedricDanny I briefly worked for Jimmy John's as a delivery driver during college, and although I had delivered pizzas throughout high school this is the story imprinted in my mind when I think of my delivery days. It was a beautiful spring day and I was delivering about $40 bucks worth of sandwiches to a nice
    via u/DaedricDanny
  • 37
    neighborhood in the early afternoon and was pretty stoked about my 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, "Oh yeah boys, JJs is here!". My first thought was how did some frat boys have a house this nice, this was
    via u/DaedricDanny
  • 38
    near a mansion. Normally I wouldn't let myself in but I decided to roll with it. I walk through the front door and this entire house starts cheering, and its filled with dads. My mouth is hanging open as they proceed to me downstairs to the "party palace", all the while I'm stepping over children's toys. When I get downstairs its the most beautiful thing I've ever seen - a mans mancave.
    via u/DaedricDanny
  • 39
    They had a pool table, a BARTENDER, and 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 drank a beer while we watched the games and they explained that every year they take a week off
    via u/DaedricDanny
  • 40
    from their firms and do this so they don't miss a second of the march madness openings. When I finally was able to leave they kept asking me to stay and party and I was pretty sure I was would be fired but they kept protesting that I stay (the situation had me so dumbstruck by its surrealism that I just couldn't leave). I finally get back to my store expecting
    via u/DaedricDanny
  • 41
    to get canned, or at the very least a good tongue-lashing (our golden rule was 10 mins there, 10 mins back), only to find my manager slightly annoyed. He said to me, "So, you met Mr. L huh?" I responded "Who?" To which he responded, "Mr. L called and said you would be running late and that your dedication in the line of duty is commendable - he's a
    via u/DaedricDanny
  • 42
    pretty wild franchise owner." tl;dr delivered to a dad party where they handed me drinks, had hired a bartender, made me stay for almost an hour, and bailed me out of trouble with my boss on account of one of them owning the franchise, and tipped me a fat $100 to party and watch March Madness with them.
    via u/DaedricDanny
  • 43
    bisexualwizard One time someone's puppy had gotten out and was running around the yard, and I helped them catch it before handing over their food.
    via u/bisexualwizard
  • 44
    RefrainsFromPart... Alright, so I rolled up to this house in the hood. 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.
    via u/RefrainsFromPartakin
  • 45
    Someone calls out at me, "Yo!" which I ignore the out of - don't go looking for 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,"
    via u/RefrainsFromPartakin
  • 46
    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.
    via u/RefrainsFromPartakin
  • 47
    [deleted] I delivered flowers for a living. One couple was getting married at an iconic, well-loved place in our city. The bride's father did not pay the bill on time for the venue. They lost their caterer and location and a $20k deposit. They had to scrape together a location (friend's backyard) and caterer, chair and tent rental in like less than a week. It
    via u/[deleted]
  • 48
    still turned out beautiful but it still was a downgrade compared to the venue they wanted. I have more stories that I'm trying to remember. A funeral home asked for flowers to be delivered by a certain time. I get there on time, and wait by their back door to deliver it. I'm sitting there waiting for like 20 mins, ringing the bell and no one answers. Finally
    via u/[deleted]
  • 49
    someone opens the door and the lady is screaming at me for being there when they're busy and parking the van in the back alley (no where else to park, And how she had been !) waiting too long for me to deliver the flowers! Meanwhile it's below zero and these flowers could die at any second.
    via u/[deleted]
  • 50
    I told my boss I'm never delivering there again. That lady was a complete and nothing she said had made any sense.
    via u/[deleted]

Want More? Follow Us and Add Us as a Preferred Source on Google.

Tags

opinion ask reddit dogs work stories funny stories pizza delivery work askreddit food delivery workplace family funny delivery opinions
Scroll Down For The Next Article