It’s Mortification Week at Ask a Manager and all week long we’re revisiting ways we’ve mortified ourselves at work. Here are 15 mortifying stories to kick things off.

1. The Condoms

I ran the campus safety office at my university, and one of my tasks was stocking all the free condom bins in the residences. Normally, I’d write all the condom companies, and they’d send me free branded ones to distribute.

One day, I realized we were running out. So I went to a local drug store and grabbed all of the condoms on the shelves, maybe 15 boxes? The checkout person looked at me funny, so I replied loudly, “Oh, don’t worry. It’s for work!”

An acquaintance in the store had to quietly let me know that everyone assumed I was a prostitute.

2. The Interview Question

My office (small department of much larger org) recently had a final round applicant come in to meet our whole team. Our director asked “Fergus” to ask the applicant a few questions about management style, as he would be supervising the new hire. Fergus clearly had given no thought to why we were asking this question or what we were trying to find out, because this is how it went down:

Fergus: How do you prefer to receive feedback?

Applicant: In what sense?

Fergus: Oh … you know … like … do you prefer to receive feedback in the morning or at night?

I don’t know how Fergus felt, but I felt like crawling in a hole and dying of secondhand embarrassment.

3. The Video Call

Had a video call to check in with my manager. I wore work-from-home uniform: respectable on top, just boxers below the waist. My laptop started dying, and I tilted the screen down to grab the charger behind it before realizing what I had just done. We went on the call like nothing happened. I’m still not 100% sure how much my manager saw.

4. The Knock-Out

Years ago, I did content work for an educational publishing house. Said publishing house hosted a conference luncheon for the vice principals of Big City to drum up sales for their wares. While the vice principals of Big City were drunk off their tits from the open bar, they had me, the content specialist, do an educational demonstration with props to somehow prove that our wares had merit.

While swinging my heavy weight on a string to illustrate an important STEM principle, a drunken attendee broke my concentration. In short order, I swung said heavy weight into my head and knocked myself out. When I came to, the drunk vice principals were cheering the premature end of the mandatory presentation and rushing back to the bar for another round.

5. The Call-Out

I was at a call center in the department that answered the “call out” line for employees that couldn’t make it in to work. The system required a reason and anyone in the building who was a supervisor could see the reasons. My coworker meant to put “out all day sick” for one employee but instead wrote “all dick sick.” I’m not sure I’ve ever laughed so hard at a typo. She was mortified when she had to contact IT to ask them to edit the comment.

6. The Miners

I was interviewing for an office position at a college and was told that I’d need a background check because they worked with “minors.” Except my brain filled in “miners” like coal miners and I had to ask to clarify. It was a group interview and about five of the people thought it was amusing when I explained, but the main person was Unamused.

7. The Intern’s Office Takeover

At an internship, I was upset that I had to hotdesk while all other employees had permanent desks, offices, or whatever. We had an available office that wasn’t being used and didn’t have any furniture in it, so I decided that would be my permanent home. I spent the morning moving furniture into the office and “customizing” my space, including extra chairs for when people came in to meet with me (WTF was wrong with me?!). I was setting up the computer when the CEO — my direct supervisor — came in and was like, no.

Thankfully he and I knew each other from a previous internship, and he had a pretty good sense of humor about it, so I completed my internship and got a great recommendation. But good Lord, that was bad.

8. The Book

In a field that is not publishing but publishing-adjacent, my interviewers asked what my favorite book was. I answered honestly that it was impossible for me to choose, but that I had recently read and enjoyed Sandy Hook: An American Tragedy by Elizabeth Williamson. One of the people on the committee visibly recoiled. I did not get the job.

9. The Note-Taking System

The note-taking system at my hospital had a bizarre glitch where it would change the name Vivian to “cocaine” or “cockhead.” With multiple doctors, nurses, and healthcare assistants using the system, it was fairly common to get reports stating, “Cockhead was in high spirits today,” or “John took cocaine to lunch and had an enjoyable time.”

The best part was that once submitted, the notes could not be deleted or altered and could be seen by any staff member or visiting physician on-site.

10. The Clock

I worked at a small magazine where we’d do round-ups of products that matched a theme. My editor found a clockmaker who made a particularly unique design that would fit in an article. She — not me, thankfully — requested hi-res photos of his clock. Left out the “L.” She was so embarrassed she had to leave work early.

11. The Interloper

My husband and I were traveling with his sister who had just started a new, remote job. She was working from our shared hotel room and on Zoom with people she had just met. My husband and I had changed and left to go to the pool when we realized we had forgotten something. We went back to the hotel room, and my husband realized his sister was on video with her brand new colleagues and decided that the best course of action was to dive to the floor and crawl across the room to retrieve whatever it was that couldn’t wait. Reader, he was fully visible in the camera frame as he army-crawled across the floor, topless, in his swim trunks.

12. The Pizza Thief

I used to work at a place that had more volunteers than employees, so parts of the building were open to the public. One day a coworker’s lunch was stolen from the kitchen — some kind of specialty pizza she was really craving. When she realized it was stolen, she was furious and asked the building supervisor to look at the security cameras. He agreed, and word went around the office at lightning speed that someone was about to get busted, so we all gathered around his computer to watch the footage.

At first we saw multiple volunteers in the kitchen. We all recognized all of them because they were regulars. Then one by one they left until one guy remained, and at this point I started getting nervous because I knew the guy very well. But I thought surely he would never steal food. He disappeared from the camera lens for a few minutes and I thought, oh thank god it wasn’t him. But then he just leaned back into the frame for a few seconds — just enough that you could clearly see him stuffing his face with a piece of pizza. And I wanted the floor to swallow me whole, because the culprit was my dad.

I just stood there in shock while all the other employees around me burst out laughing (except the pizza victim; she was still pissed). I took a lot of ribbing over this. The building supervisor took a screenshot of my dad’s face stuffed with pizza and people made all kinds of work-related memes with it. It was hilarious and mortifying. I’ve never had the courage to bring it up to my dad. One day I will. The pizza victim confronted him, though — I didn’t have to witness that, thankfully.

13. The Descent

I worked for a very large publishing company that held their annual sales conference at a glamorous hotel in Resort Town. Late the first night, a very important manager (VIM) woke needing some water, got up, stumbled through the bathroom door only to find it wasn’t the bathroom door — it was the hall door, and it had slammed shut behind him, leaving him naked and keyless in the corridor.

Figuring his only option was to go downstairs and get another key, he grabbed a small throw cushion off a chair and, holding it daintily in front of him, descended the glamorous hotel’s glamorous staircase — the kind you’d see in the Ziegfeld Follies — right in front of three-quarters of his staff, all congregated in the lobby bar, drinking.

I was, sadly, one of the few to miss The Descent, as it became known, but the story was relayed to me by the VIM’s wife, who held up pieces of paper of decreasing size to demonstrate the diameter of the throw cushion. Finally: “Oh hell, it was smaller than that, but perfectly large enough for VIM.”

14. The Sign-Off

Back in the late 90s, when I turned 20, I landed my first job with an email account. I signed all of my internal and external emails “Love, Roger.” After a few weeks, my boss pulled me aside and gently explained why it wasn’t very professional and I shouldn’t do it anymore, or it might color how people viewed me at work. I was genuinely stung at the time, but now anytime I think of my early email habits I want to chew my own face off with embarrassment.

15. The Therapist

I’m a therapist and once used the term “raw-dogging it” in session when referring to trying to manage anxiety without therapy or medication. I don’t know what I was thinking.