6 Embarrassing Work Stories That Will Make You Cringe

Ever walked around with toilet paper stuck to your shoe or misspelled your co-worker’s name? Then these stories might make you feel better about yourself…


Sometimes Opposites Just Don’t Attract
My client fell in love with me. Awkwarddd. He followed me around constantly. He would not stop looking at me in meetings and I even had to walk backwards away from him so he couldn’t look at my butt. I had other clients asking me what was up with him and why he was always around me. To top it all off, this was when I was 8 months pregnant and he wouldn’t stop looking at my belly and asking questions about the baby. Eventually he switched to another one of my coworkers.

– Brittany

The cringe-factor is high on this one. Unfortunately, some people just don’t know when to draw the line between personal and professional. Navigating these waters can be tricky, especially when you are dealing with a client instead of a co-worker.

If this happens to you, try to be as professional as possible and hopefully they will get the hint. If not, you might have to enlist your boss or HR to back you up.

You Talking To Me?
I meant to send one of my coworkers a message on our system complaining about another coworker… but I sent it to the other coworker by accident. So I trash talked the person to the person I was trash talking. It was a weird scenario where she knew about the problem, so I played it off like I was telling her something new about the issue. She’s too nice to call my bluff so she may secretly hate me still.

– Anonymous

Ouch. Thinking of the three-way phone calls in Mean Girls, anyone?

It can be incredibly frustrating dealing with co-workers, and sometimes we all need to vent. But never, ever, under any circumstance do this in writing. Things like that can come back to bite you if it falls into the wrong hands. Try finding your zen with yoga – and if that doesn’t work, talk all the smack you want when you get home.

Single Male Seeking New Pants
In the middle of a presentation, I had to plug in my laptop because the battery was low. I bent over to plug it in and my pants ripped open. The hole was so big someone offered me a sweater to tie around my waist. I could have died right then and there.

– Jason

Talk about being the butt of the joke.

Honestly, I’m not sure if this one could have been avoided. My only advice is to make sure you have everything ready before a presentation, including plugging in your electronics. At least that way your pants will rip when no one’s around.

Angels We Have Heard… Get High?
I used to work for my church. One time I prepared the program for the Christmas service and I accidentally typed out the name of a song wrong. I wrote Angels We Have Heard Get High instead of Angels We Have Heard on High! By the time I noticed the mistake the service was underway. People still talk about it to this day!

– Angela

Here is a pleasant – or not so pleasant – reminder that we always need to proofread everything we write. Read it, re-read it, and then read it out loud… even if it gets you questionable stares.

When You Gotta Go, You Gotta Go
I had just started a new job and had my first big meeting. Not only was this the first time I would be meeting the Board of Directors, it was also my first chance to impress my new boss. I spent every last second prepping for the meeting and as soon as I walked into the conference room, I had to pee – bad. I didn’t want to offend anyone in the meeting by excusing myself when they were talking so I decided to hold it. The minutes went by and as soon it was my turn to speak I was bursting at the seams. I flew through my presentation and didn’t even ask if there were any questions before running to the bathroom. To make things worse, I had to sneak back into the room and couldn’t look anyone in the eye for the rest of the meeting.

– Anonymous

Okay, this may or may not have been me – I cannot confirm or deny. But if it was me, it’s not my fault I have a child-size bladder!

Anyways, the moral of this story is simple: no matter how busy you are, always make the time to go to the bathroom. You never know when you’ll have to go and you don’t want to end up in the same situation as me Anonymous.

It’s Raining Men!
I sent an email to some high-level execs to invite them for drinks at the Foxes Den in Toronto. I got a lot of confusing responses because some people thought I was inviting them to the Foxes Den Male Strip Club, not the Foxes Den Bar & Grill…

– Ranpreet

Lord, have mercy. This is why I Google everything.

Before you invite anyone to a function, you should always look up the location. Not only can you read reviews to find out if it is an appropriate place, you can also identify red flags like this one. While you’re at it, sending the full name, address, and web link will help you avoid situations like this altogether.

Do you have a story? I’d love to hear it! Send it to me on Instagram @melissastuckless or Twitter @melstuckless.