28 People Tell The Story of Their Most Cringe Day at Work

The Office is a super popular television show because it’s hilarious, but listen – none of us would actually like to work in that office, right? Michael Scott is cringe enough to watch on television; can you even imagine having to deal with him in real life?

I’m sure some of you have had similar experiences, because it these 28 stories are enough to go on, it seems like there’s a lot more cringe going on in the workplace than we’d like to admit!

28. I would pay to see this video.

“We had mice. Boss man was terrified of mice and a total skinflint who didn’t want to pay for an exterminator. His big idea (I s*%t you not!) was to give me cotton to put in my ears and a blow horn.

He then opened the back door, closed all other doors in the little shop, and I had to attempt to herd mice out of the store with a f****** air horn, with cotton balls sticking out of my ears.

I tried to explain why it wouldn’t work, but he essentially told me not to worry my pretty little head over it, and that was my entire afternoon. Most ridiculous s*** I’ve ever done at a job ever before, and ever since.”

27. This…takes a turn. Be warned.

When I was in my early 20s, I was working at a restaurant with the world’s nicest and most innocent group of guys. One weekend, we threw a bachelor party for one of the waiters who was marrying his HS sweetheart.

Beer! Strippers at someone’s house! Crazy!

We all hooted and hollered when the strippers tore off their clothes and walked around the room to each guy. We whistled and giggled when the bachelor got a personal show with whip cream. Good times!

As the girls were ending the show, they asked if anyone had any requests before they packed up. One of the cooks, who was at least 20 years older than most of us, walked over and had a serious, five-minute conversation with the girls. He then turned to us and said that we all had to cough up $300 if we wanted to see something special.

Without hesitation, we handed the money to the girls and sat back in anticipation for what was sure to be a lovely show!

He laid down on the floor and both girls p%*sed and s*%t on him for the next five minutes. Guys were gagging. The bachelor started crying. I screamed in terror. One guy walked over to them and yelled, “Why, Why, Why???” It was if the devil himself, in mere seconds, had snatched the innocent souls of 15 naive idiots.

The show ended in silence. The girls freshened up and left with their “ride”. The cook slid on his jacket over his soiled clothes, walked out into the cold night and never returned for his shifts.

26. This cannot be true.

“It was this guy’s last day with the company, and the managers brought in a cake for everyone to share. A very nice farewell gesture.

Except he wasn’t moving to a new city or leaving the company for a new job. He had gotten fired. The managers literally fired this guy, then called everyone into the kitchen and said “Okay, today is Steve’s last day with the company, let’s have some cake!”

Most oblivious, socially awkward, tone deaf moment imaginable.”

25. The DD always sees some stuff.

Just recently went to my girlfriend’s vet office xmas party at the owner’s very nice house. The party is known for everyone getting extremely wasted.

I’m driving so i stayed relatively sober, my gf on the other hand did not. She was already quite tipsy off of all kinds of mixed drinks. I head to the bathroom down the hall for 5 min, come back to realize she had taken 3 shots (2 is her total drinking limit). Fast forward about 10 minutes and she’s absolutely sloshed.

She requests to go to the bathroom and starts asking everyone the quickest way to get there like we’re about to go on a road trip or something. I escort her carefully and let her do the business. While waiting i got caught up talking to a bunch of coworkers and kinda forgot she was in the bathroom.

About 15 min later she comes rushing out saying we have to leave because she does NOT feel good. I inform everyone we are going to head out when i hear someone yell, “Oh F**k” from the bathroom hall.

Turns out in that 15 min, my girlfriend managed to completely break the toilet in half causing the plumbing pipe from the wall to explode as well which started flooding the room. As an added bonus she decided to start throwing up at the front door as well.

Lets just say i sobered up real quick.

Anyways, the folks were super supportive of it, even though they had to replace the flooring plumbing, and the toilet. Didn’t even make her pay anything. The owner also posted pictures on facebook of his broken toilet and said it was the best party they’ve had in awhile.

24. Not exactly a class act.

“After a successful project, owner of the company invited everyone out to lunch (about 12 employees) at a nearby restaurant by the office. Little did she know, the place was very expensive, so she bounces early before the check comes, stating that she had a client call.

She gives us money to pay for her meal and takes off, leaving the rest of us to figure out the check. It also turns out she didn’t give us enough money to pay for her potion of the check so someone had to throw in a few extra bucks to cover that.”

23. Per your request…

I work with a woman who cc’s her boss on all emails.

Her boss follows up on all of the emails 5-10 minutes later.

They looks like this:

Woman: “Hey Ganglebot, we’re starting this new thing so can you send us X, Y and Z when you have a chance – thanks!”

Her boss, 5 min later: “Ganglebot, as per [woman’s] initial request, we need these things to move forward. In our previous meeting on May 4th, at 2pm you indicated you could send these to us. I ask you to please send these along ASAP as our initiative depends on good information. Please confirm receipt and indicate when we can expect these documents.”

22. What is “proper warehouse clothing?”

“I used to work graveyards. Once a month I was required to come in on Friday afternoon for a staff meeting at 1PM. This was essentially forcing me to come into work at 3AM for regular people, just so I “felt included in the warehouse”.

Also, since I did not work Friday/Saturday nights, it was essentially having me show up on a normal persons Saturday at 3AM. She had the gall to yell at me for showing up in my pajamas, and not proper warehouse clothing….”

21. It’s always best to clarify.

I was offered a job at another location. I told my boss about it and my current company offered me a raise to stay. I took it. It’s been 2 months and I haven’t seen the raise in my paycheck yet.

UPDATE: I emailed my boss and asked for an update. They assumed I understood that the raise would begin at our new fiscal year which starts July 1. So it will be in my next paycheck.

20. A true Michael Scott move.

“A few coworkers and I competed in a local Office-themed trivia contest. We came in second place, and one of the prizes was a “World’s Best Boss” mug. We brought it into work and displayed it proudly like a trophy in one of our offices.

My boss–who was not involved in the contest, has never seen The Office, is not friends with or well-liked by any of us, and is a huge idiot–saw the mug in someone else’s office and just took it.

None of us could figure out where it had gone until we saw her drinking out of it.”

19. So very petty.

Lately whenever the mother of one of my students tees off the father (they divorced >4 months ago) he will send all three of their kids in mismatched clothes with shirts that have some variation of “I love my Dad” or “Daddy’s kid”.

I have not seen the same shirt twice and believe mom throws the shirts out and dad just keeps buying more.

18. The awkwardest of awkward moments.

“I had a boss who got a promotion to senior manager. The very next day he pulled into the parking lot with a BMW 1-Series. No one on my team even knew they made a 1 series (cheapest possible BMW/badge car). He gets out wearing a BMW polo and a white BMW hat. He offered to take me to lunch in it.

He jumps on the highway, adjusts his BMW hat and says to me, “I don’t exactly do 60 in this thing!” does a little triumphant laughter and starts going 80. There was a cop on the bridge above us. We were immediately pulled over. I will never forget the look of defeat on his face.”

17. The secret is out.

I manage all the tools, parts, and materials for a small electrical company. We have a ton of little fittings, couplings, and such that are very small and have multiple parts. We recently let one of our journeymen go, and I’m in the process of clearing out his van.

Turns out he was hoarding tens of thousands of fittings in his van, all mixed together with absolutely no organization. To top it off, at least 60% of them were completely disassembled before being just chucked in to drawers, boxes, and bags along with mixed bolts, nuts, fasteners, etc., so it is now my job to take these collections of assorted hardware and dump them out, separate them, and reassemble as many as I can before restocking them in my already overflowing shop.

16. Childish behavior.

“One morning my boss walks out of his office asking if anyone wants the other half of this huge bran muffin he had for breakfast.

Everyone there said they were fine and the boss went back into his office.

Later, around 12, an employee comes in for her shift with a box full of doughnuts to share with the office. Everyone came up and took one thanking the employee for bringing in the treat. The boss was visibly mad that everyone went for the doughnuts and no one wanted his half of his bran muffin. He was just a big grump for the rest of the day.”

15. There’s never a simple fix.

A third party keeps insisting that an individual worked for my company. They did not. We have searched everywhere. We have punched in every variation of their name, birthday, social security number into our system. Dude didn’t work here, and “Well this other woman says he did” isn’t an argument.

ETA: As much as I appreciate all the replies, this is not my first rodeo as an attorney, and I wouldn’t be complaining if this had a simple fix like “tell them to f**k off” or “stop replying.”

14. Was his name George Costanza?

“My manager tried to get the nickname he had chosen for himself to catch on. The nickname in question was “Hollywood”. He would introduce himself to new workers/visitors/etc. as Hollywood, one of us would say “no one calls him that” and he would just be like “well…. everyone calls me that.”

13. Sounds like time to find a new job.

Bar manager and 20% of the staff quit. Owner hasn’t hired anyone. It’s been 3 months.

No one can take unexpected days off or call in sick and inventory is at an all time low. (Except the kegs. So. Many. Kegs.) We keep running out of f**kin everything. I (and others) have offered to help over the summer and nothing has come of it.

The restaurant is expanding and we need more employees but my boss is too focused on having us dust (during construction), replacing glassware with crystal, and setting up public accessible training courses to bother with actual management.

Oh, and communication is non existent, so I regularly show up to work and have no idea where s*%t is or what the new procedures are.

12. I bet she drove something sensible, too.

“As a blizzard approached, he offered to drive home anybody who needed a ride because he’d just bought a new “badass” Hummer H2 that “could drive through anything”.

And hour later, he and three of my coworkers are sitting in his new SUV in a snow drift on the side of the road, waiting for the wife of one of them to pick them up.”

11. That guy is a mess.

It’s my bosses birthday, not a lot of folks respect her. I’m new to the department and was asked by Don to collect money on Friday to get her flowers. He was going to bake a cake and bring it in. He was sick yesterday so didn’t come to work. I collected a measly 19$ from others, awkward af because no one even likes her, topped it up with my own 10 to get a decent bunch of flowers, bought yesterday evening and brought in this AM.

Don is in and says “I couldn’t find the money you collected, do you have it” I said “I used it yesterday to buy the flowers, wasn’t that the plan?”

He replies with an attitudey “well no…”

I ask why it matters and he says “well I couldn’t bake the cake because I was sick so I don’t know what we’re going to do now if the money’s used up, we can’t get a cake now”

Another girl nicely chimes in that she will run out and grab a cake and don’t worry Don it’s all fine. Don’s a snippy guy so I don’t bother asking him how I was to know he’s too ridiculous to go get a cake himself.

Others are running around asking me if I’ve seen the money because apparently Don’s making it well known that I was supposed to collect money but no one has seen the envelope (obviously, I took it yesterday), then I have to explain that I used all the money so I look stupid.

Keep throwing in that I was doing exactly as was asked of me but jeez, Don, would it kill you to communicate your change of plans to people???

10. What would possess a person?

Our payroll manager got trashed at a Christmas party a few years ago and started insulting people and telling them that they weren’t worth how much they were getting paid (while quoting the actual salaries).

She was fired the next day, but didn’t even remember what she’d done.

9. And don’t forget the TPS reports.

Everything is done in an improvised fashion even when it’s identical to something we’ve done a hundred times before. They refuse to create any kind of system or structure for doing anything and it drives me up the wall. Every single time, every question, every form, every action, everything, needs to be run through a hundred different people and approached as if it’s a brand new thing, even if it’s routine paperwork we do multiple times a week. It’s the most incredible waste of time.

Let’s say I traveled from Phoenix to Tucson and I need to be reimbursed for gas.

I’ll go pull out the exact same piece of paperwork I used last time. I’ll fill in the extremely basic blanks that I did last time. Name, travel date and time, mileage, gas receipt, sign and date. Submit the form.

A day later, I get an email. Oh hey here you put “Tucson” but you need to put “Tucson, Pima County, AZ.”

Make the change. Ask if there are any other changes. Nope, looks good. Resubmit.

A day later, I get a phone call. Oh hey here you put “Jay J. Jameson” but you need to put “Jay Jonah Jameson.”

Make the change. Ask if there are any other changes. Nope, looks good. Resubmit.

A day later, someone pops in my office. Oh hey here you put “Pima County, AZ” and “Jay Jonah” but it needs to just say “Tucson, AZ” and “J. J. Jameson” oops.

Make the change. Ask if there are any other changes. Nope, looks good. Resubmit.

It finally goes through.

Two weeks later, I travel from Phoenix to Tucson and need to be reimbursed for gas.

I pull out the final version that finally went through last time, just two weeks ago, after all the changes. I change nothing except the date/time and attach the new gas receipt.

A day later, I get an email. Oh hey here you put Tucson, AZ but now it just needs to say Tucson. Oh hey here you put Phoenix but you didn’t include the zip. Oh hey here you put J. J. Jameson but it needs to say J. J. Jameson Jr, Esq. Oh hey here you put that it’s 113 miles but we decided to start rounding to the nearest five so it should should 115 miles. Oh hey here you put 115 miles but an hour ago we decided it needs to be rounded to the nearest ten-thousandth of a mile. Oh hey we decided to do away with zip codes on these forms.

Every. Single. Time.

8. No one wants to see that.

First year at the company. Married CEO all over an employee pretty much in front of the whole company. Awkward AF. Both really trashed.

The fact that they didn’t start making out in front of everyone was a Christmas miracle.

7. If you’re good, I guess you get away with it.

I have a vendor who gives me the same answer every day that I email him: “Let me check and get back to you.”

His shipment has slipped by over two months at this point and it’s driving me nuts.

He’s doing the same thing to other people in my office on other projects. He’s on a quick list to be blacklisted, but unfortunately, the clients love his stuff.

6. That escalated quickly.

When I used to work for a large corporate law firm – a guy and a girl who both worked in the accounts team got in an argument. One thing led to another, and the girl threw her glass of red wine over his white shirt.

Without missing a beat he just grabbed her by the throat and started choking her.

This was just off the side of the dance floor, in front of 300+ staff.

5. Just hang on.

“Do this task. What do you need?

– I need 30 computers and 20 USB3 flash drives.

– Here’s 15 computers and 7 USB2 flash drives.

– What? I need 30, where’s the other 15? And these flash drives won’t do, the system won’t even work with those.

– Budget cuts, sorry.”


“How’s this task going along?

– Everything is set to go, but as is it won’t fulfill the task.

– What’s keeping you from doing the task?

– I need 15 more computers and 20 USB3 flash drives.

– Ok, we’ll order more ASAP, they’ll be here in two years. Make sure everything’s running by September though.”

Are things like this everywhere or is it just at my job?

4. Actually appalling.

We had a “Mardi Gras” themed holiday party. One guy decided to bring his saxophone and be a “jazz man”. Normal enough, right?

Well, he also thought that to be a “jazz man,” he needed to show up in bl**kfa*e.

3. That’s the kind of thing that makes people go mad.

Girlfriend took the time off in advance to see a best friend she hasn’t seen in two years for literally one day.

Work is currently telling her that they’re scheduling a mandatory employee meeting everyone needs to go to or else you get fired.

Keep in mind there is barely anything important that ever gets announced at these.

2. When it’s all caught on camera.

I worked at Maccas and we had a work party. Some of the crew volunteered to run the night shift while the rest of us went 10pin bowling and drank scrumpies. I was a manager, so I got to see the camera footage the next day…

It was of me, walking around the restaurant and kitchen with my pants down, shaping my b**ls to look like a brain and making people look at my taught scrote. There were also brown-eyes and squashed-rats, which is where you press your d**k and b**ls up against the glass. That was me in the drive-through window. I woke up horrified and knew I was in trouble.

There was a small fallout. I miraculously didn’t get fired; no one formally complained.

My punishment was to wash car windows as they went through drive thru on my day off and donate the tips to the Ronald McDonald House charity.

1. Insecure much?

“My boss makes me walk 2 meters behind him because I’m tall and he’s short.”

Man, I have so much secondhand embarrassment from this post, y’all! Argh!

Do you have a story that would fit on this list? Share it with us in the comments!