20 Embarrassing Workplace Confessions.

What's the most embarrassing thing you've ever done at work? Does it STILL make you cringe? (Or is it still fresh?) Cheer up; at least you're not one of the 20 poor sods on this list (hopefully).

June 20, 2023

We all embarrass ourselves at work sometimes.

Whether it’s tripping over and spilling coffee everywhere…

Accidentally insulting someone with a stupid, misjudged comment…

Mistyping a word on social media so that it ends up saying something rude…

So, in the spirit of making ourselves (and you) feel better this week, I’ve been searching the internet and asking my co-workers for their own most embarrassing office stories and workplace confessions.

And here are the top 20, funniest ones I could find...

Always Check Your "To" Box.

Workplace Confession 1.

“I sent out an angry tirade about my incompetent team members to my boss. I think I actually used the words ‘a disgusting rabble of idiots.’ Didn’t realise I pressed ‘Reply to all.’ Pretty awkward.”

Workplace Confession 2. “Sent the following to the ENTIRE office: ‘Really sorry I couldn’t make it last night, I’ll make it up to you this weekend though ;)’ My 'secret' office romance finished not long after that.

Workplace Confession 3. “We nicknamed one of my clients 'Dick' - his name was Richard but "Dick+His Surname" created a pretty funny, popular insult (I bet you can see where this is going). So I was emailing my boss about him (mostly nice things) and called him Dick 3 or 4 times within, before pressing send. Obviously, I'd sent it to Richard instead of my boss. So embarrassing and he did not see the funny side."

Workplace Confession 4. “I sent a really embarrassing, romantic poem to this girl at work via email. Yeah I know, how romantic. Anyway, I could see her cracking up from the other side of the room which was bad enough, but then I received a forwarded email from her, with my email attached, sent to the whole office. It said ‘look what Tom just sent me, so cringe.’ There are two Toms in the office, I am one of them. She cc’d in the wrong Tom – something which people soon realised.”

Workplace Confession 5. I sent this email: “I hope that nasty little dog finally dies so we don't have to hear about it anymore!” intended for my colleague, to my boss, about her dog.

Know Your Audience (Better).

Workplace Confession 6.

“So, I don’t really like babies and I literally cannot stand it when people just hand me their baby, without asking. So my boss came in with her new child and asked if I minded holding her for 5 while she nipped to the bathroom. I completely panicked and blurted out ‘how dare you assume that as a woman I would want to hold your child, I do not like children’ and stomped off. I honestly have no idea what came over me!”

Workplace Confession 7. “Probably when I asked someone when their baby was due. In fairness, they had the same name as someone else in the office that was on Maternity leave. Still didn’t go down well! You never think that type of thing would happen to you, till it does.”

Workplace Confession 8. “I wrote what I thought was a hilarious joke for the end of a presentation to my whole company - it was a knock-knock joke. I won't even repeat it because it makes me cringe so much. Anyway when I got to that part, no one said 'who's there' so I had to MAKE someone say it and then, when I left a brief silence for everyone to laugh, no one laughed. It was just dead silent. I've never gone so red - my whole body was burning."

Workplace Confession 9. “I was at a party once with my husband and the big boss came over. I don't know why, but his name completely slipped my mind. I ended up introducing him as ‘mumble-Jack-mumble’. His name is Mark.”

Workplace Confession 10. “I was having a joke around with my boss via email because we’ve always had a good bit of banter. Then all of a sudden, the HR Manager calls me into his office to discuss my ‘inappropriate behaviour.’ I basically got b****cked for ‘flirting’ with my boss who is married. I’m pretty sure I was joking about cheese at the time!”

Never Assume You Are Alone In The Toilet.

Workplace Confession 11.“I was in a meeting and desperately needed the toilet, but felt too awkward to just get up and leave so I waited and waited. Eventually it was all too much so I ran out. I had to choose between 2 flights of stairs (back to our office) or straight out to the car and stupidly, I chose the latter. I took off my tights and just stood casually weeing, praying that no one would notice.”

Workplace Confession 12. “In my first week at my new job I blocked the toilet. Far too shy to admit my soul-crushing mistake, I attempted to re-flush. WHY?! I’ve never left a room so quickly; just listening to the splashing sounds of liquid spilling out onto the bathroom floor.”

Workplace Confession 13. “I was having a really bad day at work and felt like I was going to cry, so I took a loo break to call my boyfriend. It was silent in there so I proceeded to moan and bitch for 10 minutes about how I was going to stomp out in a blaze of glory. Then I heard the toilet next to me flush! I ran away so I still have no idea who heard me!”

Workplace Confession 14. “I don’t know exactly what happened, but apparently at some point during the Christmas party (at our office) I was found in a toilet cubicle, knickers round my ankles, with clogged up toilet water (that had overflowed) all over me. I woke up at our HR’s house, on the sofa, in her pajamas.”

Workplace Confession 15. “I run the tap in the toilet at work so that people think I’m washing my hands. I’m not.”

Just STOP, please!

Workplace Confession 16.

“I had to get the IT guy to come and sort out my computer because I’d “accidentally” downloaded some porn and icons and things just kept popping up everywhere.”

Workplace Confession 17. “I like to chew things. A lot of people do! But this one time, I went a bit overboard during a big sales presentation and as my turn to speak approached, I somehow managed to pierce my lip with the staple I was chewing. I shrieked, swore and bled all over my notes.”

Workplace Confession 18. “I was recently delivering a baby and as soon as she popped out she was quite slippery, she fell out of my hands right onto the ambulance floor. In the end it was okay, but the mother almost literally murdered me (understandably of course).”

Workplace Confession 19. "On my first day of work, I accidentally called my boss “daddy.” (I’m well aware that at the age of 33 this is probably not an acceptable term for father, but there we go). Everyone heard."

Workplace Confession 20. “I text my boss (Sarah) something I’d meant to send to my girlfriend (Sarah). I’m not even going to lie, it was pure filth.”

Want to read more?

People across the world have done some pretty damn embarrassing things in their time (click here to see some more...)

Recruiter Pro Tip. I know sometimes it might feel like the world is crumbling around you and that your co-workers will never ever forget what you’ve done (or said). But it will get better, believe me! Or at the very least, take comfort in the fact that we’ve all done it at some point (yes, even recruiters make mistakes!!!)

If you’d like to carry on reading more stories exactly like this then click on the links below...

Happy Friday.

Coburg Banks - Multi-Sector Recruitment Agency
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