25 embarrassing work moments between boss and employee that are a total laugh riot
A person is bound to let loose once in a while, sometimes these moments just turn very awkward.
Almost everyone has faced an embarrassing moment or two at work. Whether it's sending a text to the wrong person, fumbling during a presentation, or something more memorable, these slip-ups can leave a lasting impression. And in the professional world, where you're expected to be at your best, there's no blaming it on a drunken mistake or confusion. But since we're all human, these moments happen—and some are so extraordinary that they turn into laugh riots, not just in the office but on social media too.
Some of these stories have become popular on X. As remote work becomes more common, so do these awkward moments—like pets or children making noise in the background during important meetings or accidentally leaving your mic on while venting about a coworker. While these moments can feel mortifying at the time, they often turn into hilarious stories that people love to share. If you need a laugh, check out 25 of the funniest work blunders shared on X..
1. Wrong text wrong person
i just had the most awkward 38 minutes meeting of my work life, 5 mins prior to which I realized that I accidentally sent messages with eye rolls about my boss to my boss instead of my husband.
— परी ♕ (@HypnoticEyess) October 4, 2023
boss was embarrassed, and so was I.
i am hoping he forgets this nightmare,
i just…
2. It's too early for this
humiliating moment for me was when i messed up a small work thing and i was like "sorry it's early" and my boss was like "it's 10 AM" and i was like "that's true"
— Matthew (@chillwaveguy) January 19, 2023
3. Etched in everyone's memory
in a meeting this morning & at the end i quietly said "cool beans" bc im an embarrassing idiot & my boss said "brittany did you say something"
— bmo (@BurdsIVue) August 29, 2022
"i said....cool beans"
4. Why screen sharing is scary
Most embarrassing moment of my career:
— Uncle Fá (@victorfatanmi) March 29, 2023
I was on a 4C sales call with a prospective client. They asked about a particular process. I opened a framework on Google just to get the terms accurately while speaking on with 100% confidence.
Well, I was presenting my entire screen.
5. When working from home gets too comfortable
😂 Just made me remember this picture I've had in my gallery for a long time. Dude must've forgot to put off his camera. pic.twitter.com/MgAilRqx4I
— Oselumese (@Sly_DaRealestG) March 30, 2023
6. When your facts are not fun
3). A lovely man at the bar saw me writing on the board and went "ah you're a leftie like myself" and I can't think of ANY RESPONSE so I go with "Did you know we die 10 years younger than right handed people?"
— Nessa (@nessadinneen) May 13, 2018
7. Thanks for nothing
My boss just emailed me to politely let me know I had a typo on a page.
— Billie 🦕 (@BillieGeena) February 12, 2021
And i accidentally replied with "thanks for nothing" instead of noticing.
I have to quit. I'm so mortified.
8. Seriously considering quitting
Embarrassing story yall 🤠
— Nicole Parish (@TXMadeNraised) June 18, 2024
I was sitting in the office this morning talking to my boss, I stretched and accidentally farted. I'm considering quitting my job.🙄 hope yalls Tuesday is going better than mine...🫠
9. When you trust your headphones a little too much
Embarrassing moment in work this morning. pic.twitter.com/kr6Ku33JzU
— Superunknown (@PolicyOfTruth95) January 12, 2017
10. That's unexpected!
At my last job the manager told this girl her hair was too long and needed to tie it up. so the girl just took off her wig and handed it to my manager 😭 I think about this day a lot 😂
— Amz (@afaang_) November 20, 2020
11. When your boss finds things they're not supposed to
crying shaking throwing up, my boss just asked me if i have twitter and i lied and said “ofc no”. he says LOUDLY infront of eveyuone “ok mr.localsharmoot”
— abood ™ (@itsabdulhai) February 28, 2022
i want to dig my own grave and bury myself.
12. When your boss is a part of the 'inner circle'
I caught my boss jamming with Everyday at his office & im shookt to know that he is actually an Innercircle! Haha! I cant contain my happiness that i kept on giving him a high five like we're close friends.😂Later did i realize my actions were embarassing i want to disappear!ㅠ
— abbygirl. (@xyzshxt) April 27, 2018
13. Not the best day
Boss came up to me and was like oh my god grace you look horrible are you feeling okay?? and i actually like went to bed early and woke up this morning to run and journal. I was so embarrassed now i have to pretend I’m coming down with something pic.twitter.com/L1s5y30g6h
— Grace (@gracecamille_) August 25, 2022
14. Okay, uncle?
Just did something so embarrassing, I accidentally addressed my boss as uncle.
— Mato. (@thelostsiv) April 25, 2022
Him: (talked about something important)
Me: Okay uncle, understood.
Aaaaaaa stress
15. Did not expect this
Me: you wanted to see me boss?
— 💣 shackleton 💣 (@shackle_ton) August 26, 2019
Boss: sit down
*he spins his monitor around, showing my twitter*
What the fuck is this
Me: i can explain
Boss: you posting cringe bro??
Me: im sorry!!!
Boss: youre loosing this company subscriber!!
16. When you wish you could delete something from people's memory
My boss just texted me a compliment, and so I took a screenshot to send to my friend, but instead of sending it to my friend, I sent it back to my boss.
— Harrison, your fav bus guy (@random_fedora) September 12, 2023
I’m going to go ahead and die of embarrassment now…
17. When the alarms blare to signal your embarrassment
Just had my first meeting in person with my boss, and it went really well, until the end when I exited through the wrong door and an alarm blared through the whole building. So embarrassing!!!
— Vic 🔜 OCC 2612 (@incaseyouart) May 10, 2018
18. A brownie matters more than anything
Having your boss catch you stuff your face with a big ass brownie right after he gave you a two hour lecture on health, diabetes, sports and cholesterol has to rank in my top 10 most embarrassing moments at work.
— Myriam (@MyriamSchrijft) November 23, 2017
19. When you wish you had double-checked
Just remembered the time I accidentally sent my boss a WhatsApp message saying 'I'm in the bath, I'll be ready in 15 minutes' and died of embarrassment all over again.
— Heidi Stephens (@heidistephens) January 23, 2023
20. Power cuts have the worst timing
That embarrassing moment when the power went out while you’re in the middle of a meeting with your boss 🫠
— B (@beasolatorio) October 30, 2023
Him: Oh are you still there, Bea?
Me: Yep, still here. Keep talking I can hear you
21. Something more embarrassing than spinach on your teeth
I had a piece of bread with cream on it for lunch today, and when I went back to work afterwards, my boss pointed out that I had cream on the tip of my nose, which was very embarrassing 😞
— ちゅん (@zupew4kj) December 16, 2022
22. When your dance hasn't gone unnoticed
Embarrassing moment yesterday. When work was over and my boss is talking to me and she says she seen me dancing with the kids via CCTV. Lol
— lyndsey reid (@irishgirl_no1) February 9, 2013
23. A comedy of errors
Someone I used to work with drove the Boss's car into a police car. Now that's an embarrassing moment.
— Innes Blight (@InnesBlight) May 28, 2012
24. Wrong time for a question
most embarrassing moment of my life was when my manager at work hummed hungry like the wolf and i went “hey what’s that song i think i know it”. he looked at me like pic.twitter.com/tgR4YXehR7
— ellie (@tvmanias) March 22, 2024
25. When a spelling mistake is more than a human error
"So you double checked all the spellings before it went to print, yeah?"
— LateReviewer (@alatereviewer) August 18, 2024
"Sure did, boss."
"Even the spine? A typo there would be very embarrassing."
"The what now?" pic.twitter.com/mrdyyDmhol
Share on Facebook
