Our Readers Tell Us About Their Cringiest Experiences Of Their Work Lives

We asked and our readers got back with some pretty awkward stories.


For the current Workplace Diversity issue, we recently asked our readers to tell us about their cringiest, most awkward moments of their work lives.

These are some of their most awkward stories…

1. Wrong Email Address

Gloria from Modern Family looks panicky after sending the wrong work email

The time my boss, 15 years ago, a dickhead, called me at 730 and asked me to delete an email he’d sent at night, and I wasn’t to read it…
of course I read it.
It was supposed to be for the HR manager, who he very clearly was having an affair with, saying he couldn’t get away from his wife, but if she could get away from her husband next weekend then they could pass it off as working away… also told how he would stitch up one of my colleagues…
he sent it to several of us by mistake… then next day threatened to break my legs if I showed anyone… yeah, the company frowned on that I remember…
– Glenn via Facebook


2. Don’t Swipe Left

I was taking some pics of the new merch to put up on Facebook for the shop I used to work for. Gave my phone to my colleague who is literally the sweetest, quietest, shyest person I have ever met. He was trying to zoom in the pic but accidentally swiped left. The previous pic was a photo my gf  had taken of me laughing while I was in my underwear. He went bright red and immediately gave me back my phone saying “Oh my God. I am so sorry, I didn’t mean to.” I was so mortified, and so was he. We avoided each other for the rest of the day and never ever spoke about it.
– Beth via email


3. Nurse Joke

Being asked to collect Fallopian tubes from a certain department, I went I asked I waited for half an hour then my nursing brain kicked in lol
– Brendan via Facebook


4. Inappropriate Customer

This story is short but sweet, and I got a laugh out of it.
It involves a customer from a former workplace. I had been speaking to my boss and the customer walked up to me and grabbed my ass. She was in her 50s at least.
I said nothing and moved away.
After the shift, a colleague of mine came up to me and said, “You know, Mary came up to me there a while ago and said, ‘Caolán ran away from me earlier after I grabbed his arse. Is he gay or wha?!’
I laughed that that was her first and last deduction of the situation.
Another colleague later told me that she’d never seen me move so quickly away from someone in her life, that I had basically speed walked away…can you blame me?
– Caolán via email


5. It’s Not What It Looks Like

I used to work with a really good friend of mine. 100 % straight lad, very comfortable with his sexuality and mine, he used to always hug me or do silly stuff like that just to wind me up.
One morning the two of us were alone in the office, it was 8am and usually bosses didn’t come in until 10. I was checking voicemails while taking down notes. My mate calls me, I lift my head from my notes and there he is standing, pants down laughing. He thought it would be hilarious to see my expression. Of course the boss walked in in that exact moment. He just looked at us, super-awkward, and said “good morning guys” and went in his office.
I’m glad we didn’t get fired.
– Stephen via email


6. Aggressive Boss

My first job was washing dishes in a restaurant, while at the same time serving in a take-away that opened out on to the street from the back of the kitchen, which I had to constantly keep an eye on from my position beside the sink. There was no dishwashing machine, so I had to wash and dry all the plates, pots, pans and cutlery by hand.
One evening, there was a big rush in the restaurant and while I was surrounded by stacks of dishes and pots, I didn’t notice someone get behind the counter in the takeaway and rob the till. When my boss discovered the robbery, he punched me in the face and told me I was fired. When I went to get my things to leave, he said, ‘No, you’re fired after this shift. Now, get washing those dishes!’
The cook bandaged the cut on my face and I worked to the end of the shift, because I was 15 and didn’t know any better.
– Shane via Facebook


7. Wrong Number?

I used to work for a call centre part-time when I was in college. We sold several products, including two different types of weight-loss pills advertised on tv for two different (rival) companies. One of the two products hadn’t been advertised in months, that specific phone line barely had any traffic at all, while the other product was quite popular.
One morning I get a call from a customer to order the popular product. I go ahead, take the order and hang up. Few minutes later the other line rings. Everyone is busy on other calls so I pick up. It was the same customer who I had just spoken two minutes before to order the other product! She recognises me and goes “Wait, was I not just talking to you to get those other pills? Is it the same company???” I start coughing and say (in a distorted voice) “Sorry, I will put you through to my colleague, one sec.”
She totally coped it was the same person. Still bought the other product though.
– Anita via Facebook

Do you have any cringe/embarrassing work experience you’d like to share? Let us know in the comments.

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