Readers’ Top 10 Most Awkward Moments at Work

If you’re like the rest of us, you’ve caused yourself some awkward moments at work – whether it’s saying the wrong thing to your boss, having a wardrobe malfunction at a meeting, or worse.

I recently asked readers to share their most awkward moments at work – and you delivered. Here are the 10 funniest “whoops” moments you shared. (And if you can beat these, please share your stories in the comments!)

1. Misdirected love

“I told my boss I loved him at the end of a phone call. I was multi-tasking while we talked and distractedly ended the call with ‘All right, I love you, see you later!’ like I usually do with my family. I caught myself and was very confused and started rambling with such eloquent statements as ‘Oh my god! I didn’t mean that. I absolutely don’t love you….no, I mean, I like working for you but I know you’re married and I’m married, and I’m not flirting so please don’t report me to HR for harassment…’ At some point during my back-pedaling, he just hung up.

2. Hello, sailor

“I was working for a defense contractor and wanted to invite all the members of my team to a New Year’s Eve party, so I sent out an Evite using our Outlook distribution list. Or, I thought I did, until I started getting replies like ‘Am stationed in Italy but will try to make it.’ I’d accidentally used a Navy client list whose name was one letter different from my team’s. The invite went to about 7,000 sailors.”

3. Slapped my boss in the face

“I once slapped my former boss in the face. I’m a woman, he’s a man just a couple of years older than me. We had a good relationship, and we were talking and joking around. He said something sarcastic, and I raised my hand to mock-slap him playfully. (Note to younger self, that was really stupid.) He turned his head suddenly, into my hand, and it turned into a full on slap. He looked totally shocked and I was horrified.”

4. Construction zone 

“I was supervising a design update to the office suite across the hall from where my office was located. It required some light construction – drywall, painting, carpet, stuff like that. The contractor randomly asked me to come over to resolve a quick issue. As we walked around, he mentioned that the new cabinets and counters had just been installed yesterday. Without even thinking, I walked right into the kitchenette to see them. Which was unfortunate because that room was full of flooring guys who were laying the mud for the new floor onto the concrete.

In my stiletto heels, I slid on the mud halfway across the room INTO the new cabinet area, executed a weird twirl that caused my knee-length skirt to fly up, and fell through the doorway onto a roll of unwrapped carpet. I shriek-mumbled an apology and limped quickly back to my desk across the hall. I didn’t realize til later that I’d left a trail of muddy high heel prints all the way out the door and into my office.”

5. Pants disaster

“One day I was walking into work, heading to my cube and out of no where, my pants fell down. Like around my ankles. I’d like to think this was because I had lost some weight, but I honestly don’t really know. Luckily it was about 7 in the morning on a Friday when most people worked from home. I was able to quickly duck in to an empty office to fix the situation.”

6. That’s not the doorknob

“Not once, but twice, while standing in a doorway talking to someone, I reached behind me to turn the doorknob while still facing the person I was conversing with. Both times, the ‘knob’ I grabbed wasn’t connected to a door. And both times it was a guy named Andy. One more time and I would have had to propose marriage to him.

He knew it wasn’t intentional, and he was not upset by it. However, he wasn’t too happy that his being groped became a story that was told over and over again by those who witnessed it. He did finally ask someone in HR to speak to them to ask them to let it die a quiet death.”

7. The dangers of the mute button

“One time I was on a conference call for training. There was a code to punch on the phone keys that would mute and unmute the caller’s phone and I lost track of whether I had muted or unmuted. I then told a coworker, thinking that the phone was muted, that the training was so incredibly boring, I had better things to do, and I just wanted to blow my brains out every time I heard X (the trainer) speak. Well…it wasn’t on mute. Another caller spoke up and said, ‘Whoever just said that, we can hear you. You might want to learn how to mute your phone.’ Thankfully there was no way to know it was me, but I was mortified nonetheless. Now I make sure I keep the mute/unmute code posted at my desk.”

8. What’s under here?

“Our company had just moved into a brand new building. In an attempt to get everyone’s work space functional as quickly as possible, the computer techs came through and connected phones and computers, leaving the cables and wires in a mess under each desk. (This was just a big room with all our desks next to each other.)

I kept getting my feet caught in the cables while sitting at my desk and finally decided to just straighten them out myself. I pulled my chair out, got down on my hands and knees, crawled under my desk and proceeded to push back the cables when the president of the company came through, showing off the new digs to a couple of his buddies. Hmm, I thought, this is a little awkward, but maybe if I just sit still here under my desk they’ll pass on by and that will be that. They stopped right at my desk and as they stood and chatted, the president pushed my chair in under my desk. The resistance he encountered was, of course, ME, because I was crouched where the chair was supposed to go. Their conversation stopped, they stared at me, I crawled out from under my desk, stood up and mumbled something about computer cables and quickly excused myself. I might also add I was wearing a dress and high heels.”

9. Did we have kids together?

“I sent an email to my ex-husband calmly, but in a very verbose way, explaining to him his responsibilities and how we had children together so his obligation to get the child support to me on time isn’t optional as their needs cannot wait, etc. Nothing nasty, but think more broken and weary. Actually, I meant to send to my ex, but rather sent it to a co-worker with a similar name. Yeah.

His response was awesome though: ‘I don’t think this was meant for me, but the 90′s were a crazy time for everyone so who knows. Will you take a check?’”

10. Parental confusion

“I once called my boss ‘Dad.’ You know how school children sometimes accidentally call their teacher mom/dad? Well, I’m a young-30s woman who called her boss Dad. To his face. I think it was something like ‘Dad, what time is the conference call this afternoon?’”







Alison Green

Alison Green writes the popular Ask a Manager blog where she dispenses advice on career, job search, and management issues. She's also the co-author of Managing to Change the World: The Nonprofit Manager's Guide to Getting Results and former chief of staff of a successful nonprofit organization, where she oversaw day-to-day staff management, hiring, firing, and employee development.

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  • mrs

    I had a boss who did the mute-complain about the conference call-unmute thing. I always wanted her to get caught. :)

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  • Gordon

    I was using my work computer to check my personal e-mail. I had received a message from a women I had dated for a while with some classy, but “revealing” photos. I did not close out of the picture viewer when I shut my laptop. The next time I opened it was in the presence of my boss. I typed in my password, and when the screen came up it was a nudey photo…not the highlight of my career!

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  • Shannon Terry

    I’m really glad I can’t beat any of those! Is it cheating if I offer one of my client’s worse job interview moments? She was nervously fumbling with her wedding ring (even if we no better & practice .. even the best of us is human!), and it went flying off, in clear view, of the hiring manager, who was speaking. Like #8 above, someone had to go desk diving to retrieve it …. but it wasn’t my client, the *interviewer* had the only access, and she headed under in her skirt suit, hose & heels. Yes, my client was MORTIFIED and no, she didn’t get called for a second interview! She wasn’t surprised, either.

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  • Nikky Guernsey

    I feel asleep in a meeting once. My manager later told me I was hanging my head on somebody’s laptop. It wasn’t a co-worker but a vendor. I was mortified.

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  • Meredith

    The first time I ever did a virtual customer training, it was over the telephone but sharing the computer screen via a separate service. I was nervous as all get out. With minimal difficulty I finished the training, and when I said goodbye and hung up the phone, I immediately IMed a co-worker with a message along the lines of “I’m so glad that was over. I feel so incompetent and I bet they didn’t understand a word I was saying. I hope I don’t have to do this again for a long time.” when I realized that I had hung up the phone but was still sharing my screen to an audience of fifteen people 1500 miles away. Fortunately, the client never brought it up, so I will tell myself they quickly turned off their projector before I sent the offending message.

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  • Me

    After doing some renovations in our law office, we now had a fourth “overflow” boardroom that was very small, and just there in case the other three were full and someone had a meeting. One day, at lunch, I asked the receptionist if any meetings were scheduled and she told me none were. I hadn’t gotten much sleep the night before so I went into the small boardroom to sleep for an hour.
    Well, one of our more grandstanding lawyers had brought a gaggle of clients in unannounced to show them the new renovations. Before the receptionist could stop him, he burst open the boardroom door with his clients behind him to find me slumped over the table asleep. As he did this I woke up and scrambled to sit up straight, but it didn’t matter much at that point. He made a wisecrack along the lines of “this is our new boardroom, and this is one of our more overworked clerks… Sorry to interrupt, carry on!” and left. Pretty mortifying!

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  • Unfortunate Employee

    hi all, i recently started a blog called myawkwardboss.com exactly for hilarious stories like this. please feel free to check it out and commiserate!

    [Reply]

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