Servers Share The Worst Mishaps They’ve Ever Had At Work

Being a server is in no way an easy job. They (literally) have to balance everything from drinks to meals. Figure in bad tips and picky customers, and things can go really wrong during any given shift. And those are exactly the kinds of stories you’ll find right here today.

Whether it’s a server dropping a drink on a VIP guest or a crabby wedding party hiding their meager tips inside their glasses of water just to be cruel, these waiters and waitresses have had just about enough. They flocked in from across the internet to share the worst and most embarrassing moments in their careers. Thankfully, at least in retrospect, some of them are pretty funny. If you’d like to find out what those cringe-worthy moments are, keep reading.

I Forgot to Put Their Order In

For me, it’s the time that I forgot to put in the food order for a 16-top when we were slammed (peak of football season). After about 20 minutes, I’m wondering where it is, and I’m sure you know the panic that ensued when I couldn’t find the ticket for it.

Lucky for me, they had been a big drinking table, so they didn’t even notice the time had been about 40 minutes once it went out. It made me start taking one table at a time since, and it definitely helped me learn to always double-check whether I’ve put things in or not. Another one would be the time I tripped, fell, and dropped a beer glass on a guest. She was super nice about it and still tipped. Reddit user: 43catarang566

I Made His Clothing Red

When I was in college training in hospitality, we had a fine dining restaurant: silver service, the whole nine yards. One of the nights I was training, we had a special guest, none other than Mr. Heston Blumenthal. He helped the kitchen team with the menu during the day and dined in the evening.

I was really nervous about even talking to him. All the tables had wine that paired with each course, and I had just finished pouring the wine for the rest of the table. When I got to Heston, I hit the wine glass with the bottle and proceeded to knock the glass and wine all over him.

I was so embarrassed about it, but he was a cool guy and laughed it off, even though he was covered in red wine for the rest of the evening. After the ordeal, I walked into the locker room and cried till I was picked up by my mum. On the plus side, he tipped about £100 for the restaurant team. Reddit user: [redacted]

I Cost My Boss Hundreds of Dollars

I cashed out a table, and after they left, I realized I cashed them out under the wrong table. It was the same ticket price, but still, it had me nervous when it came to cash out the table that was still there. Unfortunately, it was a new place and I hadn’t served for at least 2 years, so my manager voided the payment.

At that point, I didn’t even think about the first table. We voided their payment, they already left, and I closed out the second table, thus leaving me with a $200 bill that never got paid, and the owner made me pay for it. Reddit user: [redacted]

I Handed Her the Dish on the Wrong Side

So this lady with an eye patch came in with her friend. She sat with her bad eye toward the aisle. They ordered, and I left. I had a seriously good time with my fellow servers/cooks/etc. making pirate jokes and whatnot in the kitchen, because I was kind of a jerk. Then, when I took the food out, I was handing her food to her…on the blind side!

It took a while for me to realize, so I was holding that plate for at least 10 seconds or so before I just awkwardly sat it down in front of her. The friend didn’t say a word…like, why wouldn’t you? Reddit user:  piratestronghold

I Spilled Four Drinks on His Wife

One night, I was carrying two bottles of beer with two glasses, as well as two glasses of water on a tray. The couple it was intended for…well, the guy was sitting in such a way that the chair rumpled the rug just enough so I stumbled a bit. I caught my balance but was unable to right the tray.

Two bottles of beer and two large waters landed on his wife. He stood up, got in my face, and SCREAMED at me about how incompetent I was, how big of an idiot I was, and how he wished to see me get soaking and go out in the middle of winter (this was in January).

My manager quietly ushered him over to a clean table and dried his wife off as much as possible, then gave me a new tray with the same stuff on it and told me to surprise them. She doesn’t like it when people start to threaten her workers. Reddit user: mcasper96

I Covered the Owner in Chocolate Mousse

I’m serving the owner of the pub and his family. It’s been a hectic night, but I’m bringing my A-game, and he’s just gotten through bragging about how awesome of a server I am and how much I’ve improved in just six short weeks. I go to the kitchen to get their desserts, come out, and accidentally let my elbow hit the wall.

I send six wine glasses of chocolate mousse flying across the room to shatter on the table and cover his guests in decadent whipped chocolatey goodness. I thought I was going to die from embarrassment then and there. Luckily, he and his family were cool about it; they helped clean up the mess.  They even tipped me $60. Reddit user: [redacted]

I Flashed My Guests

My first waitressing job, you had to wear a certain shirt. These shirts were provided, but they were unisex (which is ridiculous, because I have a large chest). Anyway, I chose the biggest size I could to allow my chest the room it needs. All the girls were complaining about the shirts, but nothing was done.

Anyway, one time, I go over to take someone’s order, and in the process, I accidentally knock a knife off their table. I bend down to retrieve it, and when I stand back up, I tell them, “I’m so sorry, I’ll go and get you a clean one.” Then I go to the back to grab another order. Of course, my blouse button popped, but I didn’t realize until I was at the back of the restaurant and one of the other waitresses rushed over to me. I didn’t want to work there anymore. Reddit user: Jenniferh9309

I Made Lemonade

My first serving gig attracted a lot of parents who would bring in their kids. Probably my third week on the floor one day, I went over to a 7-top: three adults and four kids.  All the kids ordered flavored lemonades. So I came back with a tray full of drinks.

At the time, I was a balancing noob, and I literally dumped the tray of drinks all over this table, sticky lemonade everywhere, and then had 4 screaming and crying kids. My mom actually came in for dinner too and was sitting two tables away trying to stifle her laughter. The parents were horrified. My tip was bad. At least my balancing has now gotten better; I haven’t dumped a drink on someone since! Reddit user: ResaresaresaServer

I Poured Something into Her Purse

This probably isn’t the worst mistake I made, but I think it’s bad because I didn’t say anything. We have a balsamic dressing that tastes really good but is also very, very messy because it’s oil and it stains anything it touches. You can probably see where I’m going with this.

So one day I’m clearing plates off a table, and this lady’s salad plate has a pool of balsamic dressing left on it since she asked for extra. As I’m clearing it and talking to the table, I realize I have the plate slightly tilted and the dressing is just pouring into this lady’s open purse. No one else noticed it was happening, so I just walked away! Reddit user: butjuicyjcant

I Made a Fool Out of Myself

I was at a nice place (“crushed red velvet wingback dining room chairs” sort of nice), and I don’t know what I was thinking, but I looked down at the champagne cork when I was opening it and blasted myself right in the center of the forehead, and it bounced around the dining room.

I also one time was waiting on a bevy of babes, as it was like a 40-top of sorority chicks for a rehearsal dinner for one of their sisters. I picked up this massive tray stacked to the hills with glasses and trotted it off on my fingertips like a stud…. Only to walk through the swinging door and have it swing back and hit the tray, which sent me into this Matrix move before I dropped like 25 glasses all over the place in front of these girls. Reddit user: [redacted]

Things Like to Slide Off…

As I was serving a margarita to a table, the bottom of the glass literally FELL OFF and landed pat on the table, ice and beverage all over the place. I was left holding a ring of glass. My guests and I were all too shocked to say anything for a few moments.

Then there was a popular side dish at this restaurant where I used to work that was basically a grease-saturated potato disc about the size and shape of a frisbee but two inches thick. I was running one of these to a table, and as I leaned over the table to drop the food in my other hand, the worst happened…. The grease disc slid off the plate my passive hand was holding and fell between the back of a man wearing a nice suit and the back of his chair. He leaned back. Reddit user: teetotumm

I Showed My Leopard Print

I have many, many stories, but this one takes the cake, by far. I split my pants across my right butt cheek while I was wearing pink leopard print underwear. I had absolutely no clue that it happened. I ended up walking through the ENTIRE RESTAURANT before a coworker pointed it out.

A close runner up: referring to the lady dining with the owner’s father as “Mrs. Owner-Last-Name.” Yeah.  Turns out that this lady was the owner’s father’s girlfriend.  The good thing about the second situation is that both of them are fairly elderly and very hard of hearing, so it’s possible that what I said didn’t actually register. Reddit user: matchy_blacks

I Dropped $300 Wine

I used to work at this restaurant, and one night, I dropped a $300 bottle of wine on a table full of California wine executives. They were, um, not pleased. I was forced to pay the restaurant back for the wholesale cost of the bottle, which was only like $100 maybe?

It was a drop in the bucket for me when I worked there anyway though, so I didn’t really care all that much about it. It was the only wine-service screw-up I had there. Also, to be honest, my only job there was to sell and serve wine. Reddit user: [redacted]

I Served Meat to a Vegetarian

So I spent some time serving over a year ago when I first got out of the military and started going to school. Anyways, after a couple of months of no actual screw-ups (and no really crazy ones past this), I accidentally served a vegetarian an omelette with bacon on it (our omelettes came default with a few very large chunks of bacon).

As they pointed it out to me, my jaw dropped. They were very very cool about it and realized I felt horrible. I got that person’s meal comped, which brings up my manager’s reaction.  My manager had to lock himself in the office for a few minutes while he died of laughter. Reddit user: Teddyismydawg

I Didn’t Get Them a New Bottle

A group of 30ish dressed-up women order an expensive bottle of bubbly. I get the bottle and put it in a marble chiller, which I set on a shelf while I prepare my linen and wine key. All of a sudden, the chiller slides off the shelf and the bottle goes rolling. Stupidly, I don’t get a new one.

So when I open it, champagne sprays all over about three women, and maybe a fifth of the bottle is now dripping off the women’s clothes, the table, and the nearby wall. I apologize awkwardly and mumble something while I walk away. When I go back to the table, they are talking among themselves, so I just pretend nothing happened for the rest of the meal. Of course, they complain to my manager, and I get in big trouble. It turns out they had just come from a funeral.  Not my proudest moment. Reddit user: sourcandyisgood

I Served Someone’s Leftovers

I didn’t check the pint glass before pouring a beer, gave it to the guy, and as he finished the beer…we both saw it. We looked at each other and didn’t say a word for about 15 seconds. I finally broke the silence by saying, “Let me go get a manager to comp your meal for you, I’m so sorry!”

It turned out that there was a piece of gum from the last customer that was stuck on the inside at the bottom of the glass. It was actually really disgusting, and I also happened to get into quite a bit of trouble for that incident. Reddit user: CanadianPablo

I Gave Someone a Cold Shower

One time, I was training a new server, and I always made them carry a tray with a glass of water around to practice while they shadowed me if they hadn’t served before. She was doing really well, so I had her bring a fresh water to a table of inebriated people that I was serving.

But at one point, she leaned over and the glass wasn’t exactly steady. So she ended up dumping the water down the back of this inebriated girl’s halter top. It was also December. I actually just laughed out loud in front of them. Reddit user: [redacted]

I Put a Fork in Her Hair

I’ve only been a server for about six months or so, and the worst thing I’ve done is I one time dropped a fork with gravy in someone’s hair when I picked up a plate.  That and the occasional bumping into people because the dining hall is too crowded.

There’s also the challenge of  when bussing tables, you have to throw away people’s coffee or tea. But don’t think that I’m a pro, because I’ve had way more close calls that I’d rather not mention. You know, just in case my boss reads this. Reddit user: mrshoppingcart

All About Medium Wines

Oh goodness, this reminds me of my own moment of stupidity that happened at work once. I work behind the bar at a restaurant, and I don’t interact with the customers much at all, as the waiters take the orders and then give them to me to make. So I am not an expert on the drinks by any means, especially the wines.

So one day, we’re really busy, and my manager asks me if I can quickly clean up and prepare a table while I have a minute free, so I do. On my way back, a table starts asking me if they have any medium wines. Me being an uninformed idiot, I simply reply, “Sorry, we only serve large or small glasses,” and they all burst out laughing. Reddit user: Drew-Pickles

I Didn’t Know Anything About Wine

I got a job at a really nice fine dining seafood place. I have never worked anything remotely upscale, or nice for that matter, and had zero wine knowledge upon my hiring, but they gave me a chance. In training, we were instructed to offer a decanter for any bottle of wine over $70.

I think it was Thanksgiving, a month into my new job, when a lovely couple ordered a $90-ish bottle of chardonnay, and per my training, I offered a decanter. They obliged. You see, no one told me decanters were only for red wine. I wound up breaking the cork, so it worked out anyway.

The table was really cool about it, and any time I run into any of those former coworkers, they give me a hard time about that one. Since then, I’ve come to love and appreciate good wine. I only lasted three months at that place. Reddit user: helloimdrunk513

I Showered Half the Bar with Water

I was bartending during a lunch shift at a horseshoe bar in the middle of a restaurant. The bartender who closed the bar the previous night did not shut off the hose inside the bar. Unbeknownst to me, the nozzle had fallen off the hook and was resting right under the service bar, where I was making drinks.

About 30 minutes into the lunch rush, I had a full bar and a mile’s worth of service bar drinks to make, just me.  All I remember is hearing yelling and commotion coming from my right, yet I continued to slave away, as I had a million and one things to do.

Finally, hearing a “WHAT THE HECK IS WRONG WITH YOU?!” towards my direction, I turned to see the hose dousing half the restaurant in water. I had been stepping on the nozzle for at least 30-45 seconds. The entire left side of the restaurant (customers, the food, everything was drenched in water.

Everyone who had food had it ruined, and men in business suits were soaked. Water was literally dripping off the ceiling. Looking back, it was kind of awesome to see around 100 people all giving me the rage face all at the same time. Reddit user: CakeSmack

I Had a “Dressing Bomb”

This restaurant had a strange system of dispensing salad dressings, which was to put them in “monkey bowls,” which were small metal bowls with no covers.  Since I had a large party, my tray was full of salad dressing-filled monkey bowls (about six of them): blue cheese, ranch, and thousand island.

I said, “Dang, I can’t believe I missed the city councilman!” and everyone broke out laughing. That’s probably one of the best things I’ve ever said in my life, as it saved my butt. After a tough first week, I ended up working at that place for a couple of years. I saw so many bowls of dressing land on the floor; it was an event that we ended up calling a “dressing bomb.”  They never changed the system though, which made no sense, but oh well…. Reddit user: texasstorm

I Put Red Wine Somewhere I Shouldn’t

My first job was as a waitress in an Italian restaurant.  I hadn’t been there long, and I thought I was just about getting the hang of things, so when I saw a group with a bottle of vino on their table that wasn’t in a cooler bucket, I thought I’d be super competent and get one for them.

My boss then appears behind me and takes the bottle out of the cooler, apologizing to everyone at the table for my huge mistake. Apparently bottles of red don’t go in coolers, which I didn’t know. I felt a bit stupid for that one! Reddit user: [redacted]

I Had a Little Spill

One time, I was serving a table of corporate VPs, and one of the servers was being a suck-up and totally overzealous, totally annoying me and the rest of the staff. As I was pre-bussing the empty plates and putting them on a tray, a server came up to me with the VP’s 6 milkshakes.

She grabbed the tray with the empties on it and forced the tray with the milkshakes into my weak non-tray hand without bothering to check for balance or anything.  The combination of the tray being too heavy for my non-tray arm plus the fact the shakes weren’t centered made the whole tray topple….

They went all over the floor, on our shoes, and splattered all over these fancy VPs.  Until that point, I was doing pretty well with the table. This idiot server’s rush to get their milkshakes out 14 seconds faster ruined my (and I’m sure their) day. Reddit user: [redacted]

A Problem with Fat

While waiting tables at Outback Steakhouse, I dropped an entire tray of drinks: 10 large glass mugs filled with ice, to be exact. They tumbled onto a large woman at the table. I can still see the heavy glass mugs breaking on each other as they bounced off her fat back. I was so horrified.

Then there was this coworker who was walking out to a table with 4 ranch salads, each with an extra side of ranch. When he got to the table, there were four people at a six-person table with no extra room whatsoever. One of the people asked him for ANOTHER side of ranch. His response: “Oh yeah, I figured y’all were fat…lovers of ranch.” Luckily, they didn’t hear him too clearly, otherwise he would have probably lost his job. Reddit user: phlarp

Too Much Information (and Evidence)

One lady at my friend’s table was having trouble ordering. She kept asking about the ingredients in each dish and was looking very worried. She politely explained, “I just had gastric bypass surgery.” Using good waiter instincts to relate to his table but bad judgment, my flamboyant friend enthusiastically responded, “Oh, my aunt died from gastric bypass surgery!”

That’s not even the worst incident. While working at a pizza joint, it wasn’t uncommon for us to pull toppings from pizzas when they came straight out of the oven. In retrospect, it is pretty gross, but whatever, it happened. One of the waitresses came to grab a pizza for her table and did exactly that….

She pulled off a meatball or something. When she brought the pizza out to her table, the entire table got quiet and stared at her. She looked down, and there was this long string of cheese that was running from the pizza to her mouth. Reddit user: phlarp

I Spilled Lobster Juice

Back when I waited tables, I had two women sit in my section who were clearly vacationers. They ordered steamed lobster. Everything went fine from the ordering to them eating, but the universe decided to have other plans. After they had finished, I went to clear off the plates…

But I managed to lose my grip on one of the plates. I poured the entire dish full of stinky, smelly lobster juice and greasy drawn butter directly into her giant purse. And boy was it a hot day. Enjoy the rest of your trip, lady! Reddit user: triknic

I Used the Wrong Pronoun, Constantly

I’m gonna switch this around a little bit. A couple once walked into my restaurant and took a table for two. After a few minutes, I went and took their order and ask them, “Would you like anything to drink, ma’am?” “Would you like anything to drink, sir?”

The “gentleman” stares me down for a few seconds and lets out, in a very effeminate tone, what she would like to drink. I do an immediate facepalm. And then I instinctively refer to her as sir by accident for the rest of the meal. Double facepalm. Reddit user: didzter

I Painted Them in Soy Sauce

I dumped an entire cup’s worth of soy sauce on someone who was going to prom from a dish they make at the Cheesecake Factory. At the same job (we wore all white), someone slammed into the back of me carrying salads with sauce on the side. My back was covered in vinaigrette until I could get a new shirt.

But as bad as that was, my coworker did something that was much worse. At Ruth’s Chris Steakhouse, he tripped and fell, completely wiping out in the dining room while carrying over $150 worth of food to the mayor of Baltimore. Reddit user: sphinctersayzwha

I Passed Out Mid-Shift

I was having a major allergy attack one day, and I knew I wouldn’t get through my shift (which was at The Melting Pot) if I didn’t take something for it. So I took not one, but two Benadryl Cold & Sinus gel caps. I’m a fairly small girl, so in hindsight, it wasn’t a great idea.

I ended up passing out cold while I was in the middle of stirring the cheese fondue at a table. When I woke up, my manager, several other servers, and the nice couple from the table were standing over me, and I was covered in cheese. Reddit user:  headtotoe

I Soaked Many People

I was working a Mother’s Day brunch at a 5-star restaurant in Las Vegas. We had our dressy little waiter coats, and I was standing by a champagne bucket waiting for something to do. A patron waved me over, and the back of my jacket caught the top of a champagne bottle.

It ended up dumping the bucket of ice as well as three bottles of champagne under this whole VIP table. The champagne popped out like someone had won the World Series or something, soaking an entire table of ten from the waist down. Reddit user: BillyZapp

I Made 300 People Go Silent

I waited tables in a country club during high school. I had to work on Mother’s Day, which is one of the busier days they had. It was a buffet, so all I had to do was schlep drinks. I had a large tray full of goblet glasses of ice water each with a lemon slice.

The night before, I foolishly stayed out late partying and felt really bad. Naturally, I messed up and slid every glass off the tray right in the middle of the dining room. Three hundred people got real quiet, and some little fool started laughing at me. I wanted to rip a hole in the carpet and jump in. Reddit user: aerosquid

I Didn’t Have His Drink

I was waiting tables at a restaurant on this particular evening, and because it was going to be a slow night, I decided to get absolutely baked. It got pretty steady, and I got myself the water pouring job. During my rounds around the restaurant, one guy said to me, “Do you have my beer?”

I said no I did not, and I walked past. Five minutes after that, he asked the same question, and I replied no I did not. A bit later he spotted me behind the bar and asked me again.”Could I have a beer?” It turns out that that’s what he had been asking me all along. Reddit user: Man4msouth

I Missed the Entire Order

Ok, so one busy shift at the restaurant chain I was at, my co-workers and I decided to take a smoke break that ended up taking twice as long as originally anticipated.  When I got back inside, I was informed I had just been sat with a party of 12. So I walked over to them and asked for their drink orders.

They told me they were ready to give me their entire order for dinner. I told them to start, and I looked down at my note pad and tranced out for a solid 2-3 minutes thinking about everything except work. I looked back up, and they were all just staring at me. I said, “Sorry, I missed that. Can we start over?” Someone asked, “Which part did you miss?” I responded, “Everything. Let’s start from the beginning!” Reddit user: ShadyJane

I Didn’t Drop the Plates, Though

My restaurant is open for lunch 2 days a week, and it’s always quiet enough that only one server is rostered on.  This server does everything during that shift: hosting, serving, bartending, bussing, the lot. Anyway, one week I got rostered on because the usuals weren’t available, and I got slammed.

Everyone just decided they wanted Thai for lunch that day. Halfway through my shift, I spilled some tea right in front of the door. I then proceeded to forget about it, clear a table, then slip on the tea on my way back, landing on my butt in front of all of my diners.  I didn’t drop any plates though. Reddit user: TheCuriousAquaristServer

I Had an Ice Cream Party

I was a bartender for 5 years. I’m making a large ice cream shake one day, and the blender starts making a weird noise like it’s jammed and not blending. (It was stuck for some reason and just building more and more pressure inside somehow every second.) But I keep it going, hoping that it will un-jam itself.

By the time I bend over to get closer and see what’s going on, the top explodes off, and ice cream splatters my face so thick all you can see are my eyes. It’s all over the ceiling, dripping on the bar/customers, all over my clothes, etc. I had to spend about an hour cleaning up with everyone laughing at me. Reddit user: ChosenBrad1322

I Showed Them the Stars

My dress got caught on a booth as I was bending over. The back seemed ripped. From below my butt to the small of my back was in view of the whole dining room, which was mostly occupied by businessmen having lunch meetings. What’s worse is that I was wearing sky-blue underwear covered in rainbows, clouds, unicorns, and stars.

Luckily, it was a 30-second sprint from the back door, through the staff parking lot, through my apartment parking lot, and to my front door, so my manager let me go change and smoke a cigarette before getting back to work. Reddit user: drunky_crowette

I Gave Them Some Feminine Products

When I handed the bill over to one of my tables, they were surprised to see there was a tampon in it. All in its glorious pink wrapper. I had to keep a spare tampon on me since I had my period that day. Unfortunately, that tampon found its way to a table of 3 young businessmen.

I just ended up smiling at them pretty awkwardly. I apologized profusely, and took their payment (as well as the freaking tampon) as fast as I possibly could. I was certainly not going to wait for them to leave after that little incident. Reddit user  imaurora

I Made a Bloody Milkshake

About two weeks into my first job at the busiest drive-thru in my hometown, it’s decided that I need to learn how to mix milkshakes. Okay cool, that’s fine. Two hours into learning how to do it and I think I’m good. Right up until the metal mixer blades bust the bottom of the cup and cut the palm of my hand.

A mostly-mixed chocolate milkshake flies all over the place. And a bit of my life fluid as well. I managed to then sling milkshake/blood off the mixing blades onto innocent customers, which was probably not the best idea in hindsight. Reddit user: reinnsreinn