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29 Unfortunate Work Fails That I'm 99.9% Sure Will Give You Secondhand Embarrassment

By Kayla Yandoli,


1. This person, who accidentally put a personal task on their work calendar (only to find out everyone in their company could see it!!!):

So this is how I learned my work calendar wasn’t private.

@madebymagnolia 08:01 PM - 17 Jan 2023
@madebymagnolia / Via Twitter: @madebymagnolia

2. This nervous new worker, who went to their first day at their very first office job, only to realize at the end of the day they had this stuck on their butt ALL DAY:
@u/PBandJews / Via

3. This pure, pure person, who came into the office dressed up as a banana for Halloween (when no one else got into the holiday spirit):
@u/Srob87 / Via

4. This person, whose hair got caught IN A FAX MACHINE, most likely giving them an undesirable hair cut (to say the least): / Via

5. This person, who wasn't smooth at all and unfortunately blew it when they tried to flirt with their coworker:

A hot guy at my job asked me if I had any plans and I told him 15 because I thought he said plants

@im_all_id 07:47 PM - 24 Mar 2022

6. This driver, who accidentally locked their keys in their truck on their very last stop of the day...and more than two hours away from the nearest spare key:
@u/AutomatonVigor / Via

7. This person, who clearly forgot to add an accurate weather forecast at their news job and totally blew it:
@u/truculentdentis / Via

8. This kind boss, who had the best intentions and set up a water dispenser for his employees, but it leaked EVERYWHERE:
@u/Mairess99 / Via

9. This person, who sadly dropped their favorite office mug on the floor before drinking their coffee (really setting the tone for the message on the mug):
@u/NobodyCARESGarrett / Via

10. This person, who put all awkward people to shame by writing a truly embarrassing note for their pregnant coworker:
@online_shawn / Via Twitter: @online_shawn

11. This person, who forgot they were supposed to work from home, and bought boxes and boxes and BOXES of donuts for their coworkers:
@u/Peencub / Via

12. And this boss, who was kind enough to buy their employees donuts only to have ANTS GET AT THE BOX before everyone else in the office 😖😖😖:
@u/Tranquil_Thunderfly / Via

13. This person, who unfortunately spilled paint all over themselves at their Home Depot gig, and most likely had to go allllll the way home to get changed:
@u/needmorexanax / Via

14. This person, who tried really hard not to drop the ball (pun intended), but accidentally made packages fly all over the place in a warehouse:
@u/Racingislyf / Via

15. This person, who forgot to set a schedule for their employees and...well, no one showed up because of it:

@AriiiGonzalezV / @worksuuuuuucks / Via Instagram: @worksuuuuuucks

16. This person, who was in the middle of an important customer service call when their FREAKING TOOTH RANDOMLY FELL OUT:
@u/TresLechesPancakes / Via

17. This person, who neglected their go-to work from home Zoom etiquette and accidentally showed all of their coworkers they were (relatably) laying in bed (instead of paying 100% attention to what was going on):
@u/Scaulbylausis / Via

18. This unlucky person, who commuted all the way to work only to realize they'd missed the memo that it was a work-from-home day:
@u/RC123TheyCallMe / Via

19. This person, who broke their only pair of glasses the second they started their work day, and couldn't get any work done because they couldn't see what they were doing:
@u/brambleburry1002 / Via

20. This person, whose coworker revealed the truth and nothing but the truth during a screen-sharing Zoom meeting:

Shoutout to the guy in my zoom meeting who was screensharing and went to slack to DM his coworker “She’s killing me” while I was talking

@eggshellfriend 09:13 PM - 16 Dec 2022

21. This confused employee, whose boss gave them a humongous set of keys for restaurants, bakeries, and gas stations, but NONE OF THEM WERE LABELED 😑:
@u/Hairy-Drama / Via

22. This person, who only had ONE JOB when their boss Brian left their company, and misspelled their name on a farewell cake (most likely leaving an embarrassing last impression):
@u/NickBrown007 / Via

23. This worker, who was so STOKED his office was providing food from his favorite expensive Mexican restaurant, but then did this with it:
@u/lapistola / Via

24. This person, who truly meant well and typed up a "for hire" sign, only to embarrass themselves with their last requirement, which reads: "Line cooks: Cook people":
@u/MrVoldemort / Via

25. This unfortunate person, who printed and posted a sign that 100% left customers confused:
@u/Poppunknerd182 / Via

26. This person, who insisted they didn't need a garbage can to protect the drinks in their office from spilling, and yet HERE WE ARE:
@u/Ckiecrumb / Via

27. This poor, poor soul, who dropped a billion plates just before working an important function (like, I can't imagine what I'd do in this situation???):
@u/saibugs / Via

28. This person, who accidentally fell back in their desk chair in front of all of their coworkers, and broke it in the process:
@u/ZEROmk1 / Via

29. And this person, who forgot to turn their office's coffee pot off on Friday and returned on Monday to find this, unfortunately ruining their coworkers' mornings:
@u/TurniptheLed / Via
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