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People Are Cracking Up At These 70 Painfully Embarrassing Things That Happened At Work
No matter how hard you try, you can’t avoid embarrassment. At some point, you will make such a dumb mistake that it will keep haunting you at odd times of day—trying to fall asleep in bed, in the shower, during your commute—for years to come.
It hurts to remember these cringey fails. But when you share them, it’s oddly cathartic. Employees revealed the very worst and facepalm-worthy mistakes they’ve ever made at work, and we have collected their most powerful stories to share with you. Get ready, you’re about to get a month’s worth of secondhand embarrassment in one post.
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#1
I was on a call with an IT guy. He sounded cute so I googled him and he asked why I was searching his name. I forgot he could see my screen.
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#2
I held the door open for this kid and I said “there you go lil man” and he in fact was a grown man of short stature. It haunts me till this day.
#3
I sometimes have to email customers receipts. I took a picture through outlook and sent it. I realized the email was wrong so I put it in correctly and pressed “use last picture taken” thinking it was going to be the receipt. Outlook doesn’t save pictures. This is what I sent.
You can’t avoid embarrassment. But you can change your relationship with it!
According to the Harvard Business Review, one of the worst things that you can do after an embarrassing moment in your career is to tear yourself down.
“It’s not productive to invalidate your feelings or use your mistakes as an indication of your worth. You did something that drew unwanted attention, and it’s perfectly reasonable that you’d want to hide for a while. But do come out of hiding.”
As per HBR, there are a few things you can do to move past a particularly embarrassing mess-up at work:
- Take deep breaths to slow down your heart rate
- Treat yourself with grace and compassion
- Embrace what really happened and get closure
- Use the situation for levity, fun, and humor
- Relive the moment with your friends, but avoid rumination
- Distract yourself and occupy your mind with other things
#4
Told a guy allergic to peanuts that chick-fil-a didn’t cook their nuggets in peanut oil, only their fries, later found out they do in fact cook them in peanut oil. I ran to his table, he had a nugget in his mouth, yelled at him to spit it out, told him the news. He got up immediately and left to go to the hospital. Nothing is worse than that.
#5
Fell asleep in my car on my 30 minute break and woke up 2 hrs later I just drove off and left. Too embarrassed.
#6
I didn’t realize I was helping out Neil Diamond. Asked for his name for the transaction. A Neil diamond song was conveniently playing, he said same name as this guy on the radio. I said “I have not a clue who sings this song”.
The paradoxical way to have a healthy relationship with your mistakes is to embrace your mess-ups. Admit that you have failed, learn from your mistakes, view them as opportunities to grow, and vow to do better the next time. In other words, move away from a fixed mindset toward a growth mindset.
Ironically, when you embrace your embarrassment, you seem more human and leave a better impression on people.
On the flip side, running away from your mistakes or pretending you never messed up alienates people and can turn your embarrassment into long-term shame. The latter can negatively impact your mental health.
#8
I genuinely started crying in front of a customer because I thought they were tipping me $100…. Turns out the money was just to cover their bill. I’m still embarrassed to this day 2 years later.
#9
I forgot to lock the doors to my job over the weekend. It’s a bank.
If you can’t come to terms with your mistakes yourself, reach out to a therapist for help. It is not a sign of weakness to ask for support when you need it. Besides, that’s a much healthier alternative to being haunted by your past for years and decades to come.
What is the most embarrassing or awkward thing that you have ever done at work that still makes you cringe when you remember it, Pandas? If you’re feeling brave, let us know in the comments once you’ve finished reading through all the stories.
#10
One time when I worked at a bank drive up window I asked a guy if he wanted a treat for his dog in the back because I saw a curly headed lil thing moving around in the back (there was nobody in the front seat either) and he goes “oh, that’s my mother”.
#11
Used to work at target in the baby section. There are strollers on display that can be pushed so people can get a feel of how they move. One was missing so I pushed it back to the spot….when I noticed a woman running towards me yelling “please stop” I was confused then looked down to see a very fresh newborn baby IN THE STROLLER. I immediately started crying and apologizing and trying to explain. Luckily the mom understood once she saw the display and started laughing. Somehow she ended up consoling me because I was so embarrassed.
#12
I was supposed to call someone, and their last name was Monserrat. I didn’t know how to pronounce it, so I left a voicemail for Mr. Monster Rat,…it haunts me to this day LOL.
#13
As a teacher…I caught my “class thug” crying and upset one day so I took him in the hall to console him and ask what was wrong. He looked at me and said it was the 1 year anniversary of when his dog passed away. I teared up and looked at this sensitive soul and told him “I’m so sorry, I too am a dog lover.” Later that day I thought harder about that interaction and realized his dog was his dawg, his buddy. He was a gang member and had been shot a year ago. And I told him I was a “dog lover”.
#14
I helped an elderly woman tuck her shirt into her pants and realized I had actually tucked her [chest] in, too. Couldn’t figure out why she was walking so hunched over. I felt so bad.
#15
A man asked if his nonfat frappe was gonna make him skinny and I panicked and said “let’s hope”.
#16
One time this lady’s kid was being super hyper and running around and I jokingly was like “aww did someone have too much sugar” and she goes “no, he has autism. He’s stimming.”
#17
I walked into a patient's room and said “wow, you have such a beautiful view from your window!” he said, “I wish I could see it but I've been blind for over 30 years.” I have never complimented anyone’s view and the one time I do it's a blind man.
#18
I walked into a pt room and said “good morning sir!” and it was a chemo woman. I still feel horrible.
#19
Had two guys come up to me with their boarding pass, saw they had the same last name and was like “oh are yall brothers?!” And they went “no we’re husbands” and I didn’t wanna seem homophobic so I just went “oh even better!” But now I feel like they think I’m some freak.
#20
Working at kohls I asked what the special occasion was for the new outfits… “double funeral for my wife and 2 kids”.
#21
Told a lady at a school show I couldn’t stand this one kid performing, and she goes oh that’s my son.
#22
I didn’t know a screwdriver was a cocktail so I went down to the restaurant basement to find one and gave it to the customer.
Howl's sleeping castle 1 hour ago
I have forgotten the joke but the punchline was related to screwdriver. I assumed that since everyone in my group drinks they would know what a screwdriver is. I mean I don't drink but even I had heard of it. So I told the joke and all i got was confused looks. Because everyone thought I was talking about the tool and of course that didn't make any sense
#23
I used to take the hospital photos of newborn babies. I walked into one of the rooms with my usual perky voice and asked if baby was ready for photos. Mom starts immediately bawling her eyes out. No one told me she had a stillborn! This was never discussed during training. I called my manager all he said was “I’m sorry. Make sure you finish the rest of the babies.” I clocked out and didn’t finish that day. I went home and cried. I didn’t stay at that job long. I can still see her face and hear her tears and it’s been 13 years.
#24
Accidentally texted my boss “omgg I hate my boss sooooo bad”.
Howl's sleeping castle 1 hour ago
Me and my colleagues were joking with our manager. And one of them asked me why don't I date the manager given that we were almost same age, close friends and single, and I replied 'yukk'. The word was out before i could stop myself. Took me 2 hours to handle the situation and get everything back to normal
#25
I let someone leave and forgot to take their iv out. My manager made me call them and ask them to come back. Their response? “Nah that’s ok. I’m leaving it in. Click”.
#26
At my last job, I accidentally shredded my bosses marriage certificate when she asked me to make a copy of it. I went to shred the copy because it printed wrong, shredded the real thing instead.
#27
I’m a speech therapist, I worked at a skilled nursing facility awhile back and one day i was trying to cheer up my dementia patient (that I had worked with countless times before) because he missed his family. I got out a deck of cards just to play a simple matching game, he was not understanding the game at all even when I gave him two choices to pick the matching card. My coworker walked in a few minutes later and informed me that he was blind.
#28
I’m a wax specialist, I do mainly Brazilians, this girl came in wearing a tampon and as I went to pull my wax strip, I noticed something was connected to the wax…. Almost ripped this girls tampon fully out.
#29
When i first started out as a cashier, I accidentally accepted a very obviously fake $100 bill and the next day my manager said “someone took a monopoly bill” and I just acted like it wasn't me and said “how dumb do you have to be to do that” basically talked [trash] abt myself.
#30
Was chatting with a patient and stupidly thought it would be funny to ask “on accident or on purpose?” when he said he drove off a bridge. He got very sad and said “on purpose”.
Joe Publique 1 hour ago
ON ACCIDENT really grinds my gears because, in ‘by accident’, ‘accident’ denotes the cause or means by which something happens, and English uses ‘by’ to express that relation: ‘by accident’ parallels ‘by chance’, ‘by mistake’ and ‘by design’. ‘On’ does not express that relation with ‘accident’. ‘On purpose’ is a different construction, in which ‘purpose’ denotes the intended basis or motive for an action. So, ‘on accident’ is incorrect in standard English. Its ‘on’ has no semantic or syntactic basis in this construction; it is simply an analogical extension of ‘on purpose’ and makes no semantic sense whatsoever.
#31
Not me but when I worked at a funeral home, someone cremated the wrong person.
#32
Well two shifts ago i dropped 4 PINT glasses of pinot noir all over my 4 top. it looked like a crime scene. they tipped me 50% though so i think they thought it was my first day. on earth.
#33
In elementary school basketball they called timeout and I didn't hear the whistle so I started guarding the opposite team while they were in a huddle.
#34
Two people came into my sandwich shop — a feminine looking one and a masculine looking one. I asked the first one, “what would you like ma’am?” She answered. Then I asked the other person, which I thought was a guy, “and for you, sir?” Then they started talking, it was a higher pitched voice, I was like “oh sorry, ma’am” then they looked kinda annoyed, then I said “oh, sir, sorry.” And they still kinda looked annoyed.
#35
Told a patient who had suffered a stroke “Sorry my brain ain’t working right today.” She replied after lifting up and plopping her paralyzed arm on the counter, “it’s okay neither is mine”.
#37
When I first started serving I thought a Shirley temple had alcohol in it and a little boy asked me for a Shirley temple. I laughed and said “nice try” and walked away.
#38
I dropped a plate of nachos on a baby.
Howl's sleeping castle 1 hour ago
This is a genuine fear for me. I am always afraid I will drop something hot or spicy on my cat.
#40
I work front desk and hung up on a prank caller using a funny raspy voice. 30 mins later a woman with an electro larynx walked in and said that she wanted to make an appointment I was mortified but she was so sweet and said it happens all the time.
#42
When i was young worked at a grocery store as a bagger. this lady bought an ice cream pint and a magazine for weight loss. idk what i was thinking but i blurted out “wow what a combo u got here!” she complained to my manager.
#43
Spilled a big bowl of hot soup on an old man, cleaned everything up, went back and got another bowl, and then I spilled that one too.
#44
This morning. I went to work with a split in my pants and didn’t notice… my bare cheek was out for all to see. A man had to pull me aside to let me know.
#46
One time I charged someone $90 for a watermelon and neither of us realized till I looked at the transactions later.
#47
I forgot my belt and my pants fell down as I was walking away from my table. Luckily I was wearing boxers, but they were space jam boxers… like bugs bunny. The lady went “oh!” And I just profusely apologized. Mortifying.
#49
I charged a patient $13,968 instead of $1,396.80 & the bank wouldn’t let her touch her account for a week.
#50
I was grating cheese onto this guy's pasta and got it ALL up in his wine glass and didn't realize, so I just walked away when I was done with the cheese and left him with cheesy wine.
#51
Not necessarily a mistake but I worked at a deli and a middle aged man wanted to try one of the hams- I sliced him a piece and as he was chewing I said “u like that?” And I was so embarrassed I think about it all the time.
#52
Working in retail I was handling a return and it was like 15 items and I said “wow that’s a lot of clothes, nothing worked I see”, he said my wife just [passed away] and I’m making the return back to our card.
#53
I had a diabetic patient that refused amputation of the foot and his foot got sooo bad… when I took his sock off his toe fell on the floor. When it happened I was like “yoooo”.
#54
I was 18 and I was a medical secretary. I would have to call patients the day before appointments and I called this one guy well call him John,and his wife answers the phone and tells me her husband is very recently deceased. I gave her my condolences and told her that I will switch his account to deceased and I will inform his doctors. So what I did wrong in this scenario was I did not immediately mark the patient as deceased and I didn’t cancel his appointment; if I don’t do that immediately then I could potentially call the same person twice. Which is what happened, I called again and told her “ whoops didn’t mean to call again” and she said “it’s okay dear” blah blah. Not too bad.. then I forgot to mark him as deceased and forgot to cancel his appointment AGAIN and made the mistake of calling his poor wife AGAIN TO REMIND HER OF HER DECEASED HUSBANDS APPOINTMENT! She genuinely sounded scared on the third call and I legit said “I’m sorry I’m so bad at my job” and hung up. Nobody said anything to me. Got fired two months later.
#56
A customer (I’d never met) told me (over the phone) he had won a weight loss challenge. He said he had lost over 100lbs, to which I said, wow, you must’ve been huge.
#57
So stupid but I called out sick from my job w an ai picture of a thermometer and they fired me so quick.
#58
A customer with his family offered to pay for “the woman over there’s meal” and pointed in the direction of a single mom and her 3 kids who they commented on how overwhelmed she seemed, i went up and told the mom excitedly that the gentlemen paid for their food, turns out he meant he wanted to pay for his teenage daughters food who was in the same direction as the woman.
Geoffrey Scott 5 minutes ago (edited)
Bob Evans: My wife helped a stroke sufferer whose husband was anxiously waiting for her while she used the rest room. Nice old couple, so we decided to comp their meal as well. They got done and went to leave and somehow found out we did it and thanked us profusely. We got done a short while later and went to leave and someone must have witnessed/learned what we did. Our bill was comped too!
#59
We were constantly told to upsell alcohol. I asked a table if they were interested in any margaritas. They told me they were there for their AA meeting.
#60
I answered 911 during a tornado and the caller said a tree had fallen on his house and he couldn’t find his wife. Out of HABIT, I asked him what his house looked like (so I could give a description to the officers responding), he responded the house with a tree in it as soon as I said it I regretted it.
#61
We were super busy, I saw a pair of girls sitting clearly hadn’t been talked to yet and I had noticed them earlier so it had at least been 10-15 minutes I went up and started blaming whoever sat them didn’t write them down and it was that persons fault they had been waiting awhile (really at this point everyone was taking tables there was no clear sections, and I was trying to save my tip) and I don’t know why but to make it believable I asked who sat them and they go “you”.
#62
I taped the wrong box up because of how fast and stupid I was moving and literally sent a lady home with an empty one. This was at a pet store. I was supposed to be selling her a pet rat.
#63
I ruined a mans sobriety by giving him what I thought was a Virgin Pina Colada it was a double & he laid out his AA chips on the table for me to see after I think about it atleast 2 times a week.
#64
I told my bald cancer patient “alright now, I’ll get out of your hair” after being sent in to do a bunch of labs, vitals, and other annoying medical tasks. It wasn’t until I closed the door and left that I realized what I had said.
#66
No cause I win, when I was working at an icecream shop a mom came in looking sooo exhausted and her kids were being so obnoxious, and she even told me how long of a day she’d had and was so excited for her icecream. She got 2 pints for her kids and 2 for her and her husband. 10 minutes after she left… I turned around and saw those 2 pints on the counter and I forgot to put them in the bag. And it was the two for her and her husband. I really wish she’d called or something but she didn’t and I have NEVER forgiven myself for that.
#67
First day on the job taking an old guys order, he asked for his senior discount and I jokingly said “you don’t qualify for one of those” (intending to “make him feel young” ig idk) then he goes YES. I. DO. and i’m like oh ok im sorry.
#68
One time Jessica Alba showed up to eat at the restaurant I was a hostess at. Idk why I didn’t connect that it was THEE Jessica alba and I told her we couldn’t sit her sooner and it was like an hour and a half wait. The manager came running out and immediately showed her to a table.
#69
One time I worked at a Land Rover dealership and I used the money counter but I had it set to 100 dollar bills and she had 20’s and I gave her most the money back like girl this is way to much money are you crazy? She was about to leave with her discounted Land Rover when I noticed and had to tell someone before my safe was WAAAAYYYY OFF.
#70
I was walking with a tray of drinks when I felt something hit my leg, slide, and then scream and cry. A little girl with a basket of toy lambs ran in front of me, I didn’t see her. And since I was walking so fast with those drinks, I kicked her sooo far. I didn’t spill the drinks though so.
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