Some of these stories at work are too funny while others will make you cringe in sympathy.

Embarrassing moments at work

Dilbert creator Scott Adams asked his readers for their most embarrassing moments, and these are the moments that were most memorable:

A professor in college was discussing the Myers-Briggs Personality Type Indicator one day. For those not familiar, it evaluates personality types as E vs I (extrovert vs introvert), N vs S (intuitive vs sensory), T vs F (thinker vs feeler), and J vs P (judger vs perceiver).

The professor was talking about how people with different personality types can sometimes run into conflict, and he was using himself and his high school age daughter as an example. He was a judger and his daughter was a perceiver, and he was describing it as such:

“So you have me over here, basking in my J-ness….and then over there you have my daughter, with her P-ness…”

It didn't immediately occur to him what he had just said, until one kid in the class attempting to suppress a laugh let out an audible snort. Then everyone in there lost it, and the professor (a very straight-laced, conservative guy who looked a bit like James Taylor) turned bright red. It was priceless.

We recently had a company meeting where it was announced that an employee had been let go.

He had a really nice, new dual-core machine [high-end computer], so when the leader of the meeting asked, “Are there any questions?”, I said, “Can I have his computer?”

Apparently, this was in poor taste.

I was fulfilling my civic duty and was ready for Jury Duty.

The judge asked a few standard questions before the attorneys could get their jab at us. When asked if I knew any attorneys I told the judge that my company hires attorneys so I know a few.

The defense attorney later asked me about this and said, “Extremely handsome man in the suit (I'm telling the story, right?), you said that you employ attorneys, is that right?”

I replied, “Yes. Are you looking for a job?”

It slipped out suddenly and I thought for a moment I'd be held in contempt or something as the whole room seemed to be laughing.

Once I saw that the judge was laughing too I relaxed.

The attorney came back strong and replied, “No, no. Well, depending on how I do on this case…”

I was a new District Attorney working in traffic court.

The DA next to me was dealing with a guy who was trying to handle his son's speeding ticket. She explained to him that his son had to be there in person. The father said that his son had been in a motorcycle accident that morning and had severed his hand.

The DA felt sorry for him and gave his son another court date, but explained to the father that the son had to be there in person next time or he would be in trouble. I leaned in and said, “yeah, up to his elbow.”

20 years ago I worked for a VAR [value-added reseller] that installed financial software systems, replacing the manual ledgers. So installing networks was also part the job, along with upgrades and the like.

As a young tech, I stood beside the senior associate as he was boasting the advantages of upgrading his basic Novell 2.0 network to Netware SFT. When the client asked ‘what does SFT stand for?' I blurted out ‘Same !$%*!$% Thing'.

Amazingly, we got the sale and I kept the job!

I work with children, who are sometimes shy to speak, so I ask them some questions about their parents, which usually helps.

The questions are: “Is your dad a great guy? Is he an OK guy? Is he out of jail?”

For the shyest kids, that last question usually produces giggles, and they open up.

Unfortunately, one kid answered “Yes, last week”.

I was once working on a grueling IT project, everyone was overworked and generally jaded and peeved most of the time.

One day this guy was walking to grab something from the printer when he drops dead of heart attack, my response was “this place will kill you…”

I spent most of the 90s working for a large telco [telecommunications company] – in early '99 they kervorkianed a major boondoggle project that had dragged on for almost 6 yrs.

After a meeting where they gave away the “swag” (mugs, shirts, etc.) they had ordered for the hypothetical launch, I was in the elevator with some people and spontaneously chuckled when a thought popped in my head. I made the mistake of sharing it when a friend asked: “they should print ‘I spent $10M on a new billing system and all I got was this stupid t-shirt' on the back of these”.

The elevator erupted into laughter except for ONE person in the back corner – the controller…


I was laid off from the company 8 years ago, but 10 years ago I approached the receptionist, who I knew was recently married and they were trying to conceive, and asked her how far along she was.

Apparently, as it was pointed out to me later by fellow co-workers, that she had been eating more as she was upset that she couldn't get pregnant.

I have said a lot of stupid things over the years, but I still believe that was my worst.

I was at a client site at a meeting. The meeting room was between the break room and the machine shop, and at one point someone decided to heat up hot dogs. The room was suddenly filled with this odd combination of the smells of cooking meat and burning metal.

I said, “Smells like 9/11 in here”.

I didn't get the contract.

[That was terrible!]

I had a meeting in a building where I used to work and went to visit my old team. While chatting with former co-workers, a new employee stepped out of a conference room across the office. I realized I knew her from the gym as she took the same spinning class and often changed at the same time. Once I placed her face I called across to the room to her: “Hey so-and-so, nice to see you with your clothes on!”

I figured it was easier on my pride to change gyms than having to explain why I thought it was going to be a funny statement.

I was a police officer in my 20's. I pulled over an attractive woman a few years older than I was for speeding, and weaving in and out of traffic. She went into a long tirade about how she was really in a hurry and what a good driver she normally was, and told me that she'd been driving for 15 years and had never even been pulled over before.

She then said to me, “Don't you know what that means?”

Without thinking I replied, “Based on the way you're driving today, I guess it means you're overdue.”

She didn't think it was funny.

Neither did my supervisor.

If haven't laughed or winced enough for today yet, check out the full list of embarrassing moments, work-related or not, in Scott's blog post and comments.

I'm pretty sure we've all done some variation of the pregnant-woman gaffe and I know I have too. And there's always the email that was intended for one person but was sent in reply to everyone.

Outside of work, I remember once going for a routine doctor appointment. My doctor was part of a student mentorship program and there was always an intern around when I visited. My doctor looked the professor role too, with a big mop of frizzy, graying hair.

It had been a long time since my last visit and while chatting, the intern mentioned that a new girl had been born to the doctor's family. I turned to the doc.

“A new granddaughter?” I asked.

“No. A new daughter,” the intern smiled to me as both the doctor and I turned red.

Question of the article

What about you? What is your most embarrassing work story? Tell us in the comments.

READ NEXT: Top 10 Funniest Job Horror Stories.

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Jacob Share

Job Search Expert, Professional Blogger, Creative Thinker, Community Builder with a sense of humor. I like to help people.

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  5. Rafael Hurovich

    One of my major “ouch!” professional moments occurred when I worked for a huge pharmaceutical company, during an internal audit. The top-ranked international quality auditor was visiting our manufacturing site, and he arranged a meeting with my line manager, who was the QA manager, a tough lady in her fifties. They started the audit procedure at the meeting room and reviewed the relevant topics to be answered by the area manager. Then I was called in to the meeting in order to answer specific questions about my area (which was Pack Artwork Development). I managed to prove we were correctly following the procedures regarding several audit points, until he made a very difficult question and I gave him a not so convincing answer, so he made a remark (“attention point”) on his audit report and asked me in a somewhat harsh manner: “- As the area coordinator, you should have had foreseen this issue!”. He took me by such surprise that I replied – obviously without thinking “- Dear Mr. X, if I had your experience and broad vision, I would be in YOUR place!!”. At this point, my line manager gasped and turned red, green, violet and other colors, wordless… The auditor then stared at me for a second, made a forced smile, nodded his head slightly and told something like “- OK, let’s check the next point”. After the audit meeting, my manager asked me “- Have you gone crazy??” but eventually this embarrassing answer earned me a higher respect from her for showing an assertive attitude and not feeling intimidated by hierarchical pressure. This chutzpah could have had me fired but the story had a happy end.

    1. Jacob Share

      Now that’s called going with your gut!

      Thanks for sharing but most importantly, glad it worked out well 👍👍

      1. Rafael Hurovich

        That’s actually called “playing with fire”!! but I was lucky enough to survive…

  6. Vicky Driver

    Too bad most of the stories are obliterated by social media options perhaps there is a glitch

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