Mortification Week: the mustache party, the hat police, and other stories to cringe over

This post was written by Alison Green and published on Ask a Manager.

It’s Mortification Week at Ask a Manager and all week long we’ll be revisiting ways we’ve mortified ourselves at work. Here are 13 more mortifying stories to enjoy.

1. The mustache party

My partner and I were in our 20s and we had just moved across the country for my grad school program. He got a job at one of those hipster tech startups that had an office equipped with Nerf guns and beer taps. True to type, the company culture was all about ironic parties, and two months in, we were invited to an after-hours mustache party at his office.

This was in 2008, when hipster tech startups and Movember still seemed like novel amusements, and I’m a sucker for a good theme. I went all out — but not TOO all out – with a cute cocktail dress, a nice bushy stick-on mustache from the dollar store, an eye patch, and a pirate hook. My partner looked a bit doubtful, but I pointed out that the mustache made no sense without a pirate patch (“like, what’s the narrative?”), applied a kicky red lipstick, and prepared to network.

It … did not go as I had imagined. Remember this was still early 2000s tech: someone had stocked the party with what I can only guess were models hired to make it seem cooler. The path to the front door was lined two deep with very tall, very blond women wearing small black dresses. They did not have mostaches, or eye patches. They smoked their cigarettes and stared at us in dead silence as we walked the gauntlet to the bar. It was too late to turn back — too many people had seen our grand pirate entrance. All I could do was straighten my mustache and work my way through the party, shaking hook-hands with my poor partner’s coworkers as I went along.

My partner worked at that company for ten years and I never saw those tall blond girls again. He has also never again let me win an argument about dress code.

2. The hat

I worked for a school district that decided the hill they wanted to die on was hats. Religious headgear was allowed, and grudgingly the few students who were undergoing cancer treatments that made them lose their hair were permitted to wear a cap of some sort, but those exceptions were a small portion of the student population, and it seems no matter how styles change, teenagers are fervently attached to wearing some sort of hat. Personally, I don’t care about hats and I had to train myself to notice them after I was scolded for not enforcing the rule.

Then for the next 30 years, I was saying some variation of “Hats off!” on at least an hourly basis during the school day. This followed me into non-school settings, and once I was confronted with the shocked and irritated face of a stranger I had sternly told to remove his baseball cap in the public library.

3. The pothole

I was part of a team working late one night on a proposal and we decided to walk across the street to grab dinner before returning to finish the work. It was completely dark out and had rained all day, which is why when I tried to leap across a patch of wet grass to land on a pothole cover, I didn’t see that the pothole was actually NOT covered, but filled to the top with water. I went in feet-first all the way up to my waist. My coworkers looked in every direction but me as I somehow leaped out of the pothole (I have never shown that level of athleticism since) and spent the dinner trying to laugh it off in soaking wet shoes, tights and skirt.

4. The drinks

At the time, I’d worked for 10 years in a community center as a new manager on the member-facing programming team. Every year, there is a two-day regional conference where community centers from the tri-state area get together to share best practices, professional development, and a night out (usually a karaoke bar). This one year, I decided to start a diet the day of the conference, so I did my best to eat very cleanly and very little … then finished the evening by accidentally getting very, very drunk. Our CEO eventually escorted me back to my room where I proceeded to vomit all night long (much to the chagrin of my roommate/colleague).

I was still so drunk the next morning that one of my coworkers had to drive me in my own car from the hotel back to the conference location, where I was unable to keep my eyes open and ended up sleeping (missing half the conference) on an office couch under someone’s coat as a blanket. I was 37 years old at the time. My CEO was incredibly understanding about it, basically telling me to never let it happen again. (It hasn’t. I’m still at the same organization in a middle management role. I also never drank Fireball again.)

5. The presentation

I was on a call with the vendor, who was presenting, when he switched his screen so I could see another aspect of the product. Up pops a document titled “How to Use Your Rabbit Vibrator.” Cue frantic clicking on his side. (He claims it was left over from a previous client presentation.)

6. Not sun

I had an panel interview where one of the interviewers arrived with shockingly red skin all over. I remarked something like, “Wow! You got some sun! I hope you were having fun!” He muttered something like “not really,” and I responded with a “oh, yard work or something?” And I think … I don’t remember … but I think … I … might have … actually called him “Lobster Boy.”

I got the job, amazingly, and discovered a month or so in that his skin condition was the result of a painful ongoing medical treatment. I melted into a puddle under my desk.

7. The ice cream cone

The summer before I turned 17, I worked at McDonald’s to save money for a used car. I worked at the counter, but we did handle food and for some reason they didn’t make us wear gloves. (We were handling money and then serving fries and ice cream with those same bare hands!) One day, two women came in with kids and ordered ice cream. As I was making a cone, I got some ice cream on my hand and I LICKED IT OFF. While holding the ice cream cone. I went to give it to the woman and she said, “I saw you lick your hand. I’d like you to make me a new cone.”

Did I then profusely apologize and immediately make a replacement? Of course not! I stupidly said, “Oh, it’s okay, I only licked my hand, not the cone,” thinking that of course the problem must be that she thought I licked her food. She said, “Yes, I know, I’d still like you to make me a new one.” I did make her a new one and didn’t really give it a second thought until years later, when I realized what a horribly unsanitary thing it is to lick your bare hand while holding a customer’s food.

8. The wrong recipient

I once worked in an office with a secretary who couldn’t stop talking. One of those people who’d even narrate what she was doing if no one was around to listen to her. One day I had a difficult project to finish, my earplugs had gone missing, and Secretary had a captive audience in the form of a new hire she was “training.” I meant to use the interoffice IM to text, “I can’t focus with Secretary chattering on, so if you need me I’ll be in the conference room. God she drives me batty” to my team partner. Sent it right to Secretary.

9. The wrong word

I worked for many years in the customer service department for our local newspaper, and one of our duties was to make calls to customers starting or restarting their subscriptions to make sure there were no issues with delivery. So there I was, making my way through an hour of outbound calls, repeating my script over and over again: “Hi, it’s Scrooge calling from Newspaper to make sure you got your paper okay?”

It was going great until my last call of day, when I instead said: “Hi, it’s Scrooge calling from Newspaper to make sure you got your pooper okay?” This was almost 20 years ago and I still cringe when I think about it.

10. The voicemail

When I was in college, my best friend and I worked for the college’s foundation making cold calls for donations. The system used an autodialer and most people weren’t answering so we were chatting and having a playful argument while we worked. As one of my calls was ringing, she said something and I said, “You know what? Don’t even talk to me” and realized too late that the voicemail had picked up and I had just left that as a message for someone. I panicked, hung up, and called again leaving a normal voicemail.

11. The cocaine

When I was newer to a job as a salesperson, I was on the phone with a colleague. We had a company rule that we could not be on the phone while driving, so I pulled off into a parking lot to go over some updates with him on speakerphone. A man came up to my car, motioned to me to roll down my window, and while my colleague was on the speaker asked me if I “I wanted a bump.” I will admit, I am a bit naïve and had no idea what a bump was but, always the learner, I said in a very polite way, “I’m sorry, I don’t know what a bump is.” To which he replied, “Cocaine, would you like some cocaine?” In the most midwestern polite way possible, I said back to him, “Oh, no thank you, I am good” while my colleague was laughing loudly at me over the speakerphone.

12. The missing word

Back in the 90s, I did improv mystery dinner theater where we sat at guest tables. Wives loved it when we singled out their husband’s and did fake flirting in character. I was at a table with a nice extended family … and in character, flirted with the dad to make him my character’s love interest jealous. He made some comment, to which I replied, “Oh, I’m just using you, but I’m going to blow you off later.” Except … I somehow didn’t say the word “off.” It was a truly mortifying, record scratch moment and I eeked out, “Oh, wow. Um, that is not what I meant!!” The entire table burst out in laughter. It was not that kind of show!

13. The accidental grope

When I was a young salesman, I was selling a woman a phone from a display, I was gesturing at one of them and turned towards her, just as she turned towards me … and I perfectly cupped her breast.