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Bad boss and coworker stories

Chris Crossed

, , , , | Working | August 6, 2026

This story reminded me of a joking coworker of my own.

I am a woman, but I go by Chris. I don’t mind being called Chris or my full name, but I don’t answer to other variations. In particular, I hate being called “Chrissy” since I was a blond kid growing up when the show Three’s Company was on, and I got teased a lot because of that character.

Fast forward to me working at a small startup as an adult. We were a tight-knit group, and we did tease each other in good fun. There was one guy on the team who, when he discovered that I hated being called Chrissy, would often call me that just to get me riled up. It was very annoying, but I knew it wasn’t mean-spirited, so I put up with it for a while.

One day, I realized that I was going about things the wrong way, since people usually called me when they needed help with something. So the next time he called, the conversation went like this:

Guy: “Hey, Chrissy!”

Me: *Instantly hung up the phone.*

Guy: *Calls back a couple of minutes later.* “Hey Chris!”

Me: “Hi, [Guy]! What can I do for you?”

He tried calling me Chrissy only once or twice more and got the same response each time. Worked like a charm!

To The Bitter End

, , , | Working | August 6, 2026

I was out shopping with my mother, my cousin, and a good friend. We had spent the whole day looking for a wedding dress for me and had already had several appointments in different boutiques. We’d been on our feet for hours and desperately needed a caffeine boost, so we popped into a small bakery café for a quick break. 

My father works for a coffee company and sometimes brings home a very mild, low-acid blend that’s supposed to be easier to drink. Even then, I still need it drowned in milk and sugar to make it tolerable — I’m not exactly fond of coffee. Normally I avoid it altogether, but today was an exception. We still had a lot left to do, and I was running on fumes.

The cashier was unfriendly from the moment we walked up. My mother, cousin, and friend placed their orders without issue. When it was my turn, I politely explained:

Me: “Hi, I don’t really like coffee. Could you recommend something with a lot of milk and as sweet as possible? I’m not familiar with the menu.”

She didn’t answer. She just started making a drink in silence. A few seconds later she slammed a to-go cup full of straight black coffee in front of me and said curtly:

Cashier: “Milk and sugar are over there. Do it yourself.”

I was stunned. I tried to explain that this wasn’t what I’d asked for, but she didn’t seem to understand what I wanted. My mother, cousin, and friend jumped in to back me up, all of us repeating that I had requested something milky and sweet because I don’t drink black coffee.

After we finally got through to her, her response was:

Cashier: “Not my fault if you can’t order properly.”

We asked for a refund, but she refused, insisting I had received exactly what I ordered.

At that point I was too exhausted to argue anymore. I walked over to the milk and sugar station and poured in as much of both as the cup could physically hold.

I choked the whole thing down. It was, without exaggeration, the most disgusting thing I have ever tasted. The bitterness still came through strongly, and the milk and sugar I’d added didn’t really do anything against the burnt taste. It also gave me painful stomach cramps that lasted for hours.

Despite everything, we actually managed to find a beautiful wedding dress later that day, but because of the stomach cramps, we almost had to cancel the rest of the tour.

Émile In New York

, , , , , , , | Working | August 6, 2026

The following happened a few years ago and has been condensed for storytelling purposes.

I work in an office for an international company. We have offices all over North America, Europe, and Asia. I’m based in New York. My boss wanders up at 8 AM and says to me:

Boss: “Remember we have [International Transfer] starting today. He’s here for two months to get [project] up and running.”

Me: “Didn’t I hear from HR that there was an issue with getting him here so early?”

Boss: “Yeah, his boss tried to delay it, but I went to [Big Scary Boss] and insisted he must start today.”

9 AM rolls around, and the new guy saunters into the office. His gait seems purposefully casual.

Boss: *Running up to him.* “Where have you been?! It’s nine!”

International Transfer: “Yes. We start the workday at 9 AM, do we not?”

Boss: “Only on paper. It’s strongly encouraged to come in at 8 AM to ensure that—”

International Transfer: “—Well then I strongly encourage you to put down on paper that my start time is 8 AM.”

Boss: “That’s not how it works.”

International Transfer: “If you say that is not how it works, then that is also not how I work. Anyway, I just came to introduce myself. I will see you in three weeks.”

Boss: “Wha… what do you mean?”

International Transfer: “I had my annual leave approved to start from today, for three weeks. Your boss told my boss that I had to come into the office today to introduce myself to you. So here I am, introducing myself to you today. But HR rules also stated that my three weeks of annual leave can’t be cancelled once approved, so I’m going to start it right now. I think I might go see The Met.”

Boss: “That’s not gonna fly. You’re here to start [project] today.”

International Transfer: “I did, by introducing myself. See you!”

Boss: “What makes you think you can just walk out and take three weeks of vacation just like that?!”

International Transfer: “I’m French. Au revoir!”

True to his word, the French Transfer just waltzed out. [Boss] was livid, and called his boss, who spoke to the European Boss, and after much shouting, it was established that European law was very strict and his vacation time (of which he gets six freaking weeks a year) was approved and couldn’t be taken away. This had been explained to our boss, but he had assumed that the vacation time could just be cancelled and didn’t look at the European HR rules. 

Because our boss had insisted on the French guy coming in today, the company had paid for the business-class flight from Paris to New York for him. That’s when he decided he’d be vacationing in New York for three weeks, with flight and fancy hotel paid for by the company, thanks to our boss’s insistence to get him in the office TODAY. 

He came back three weeks later and used his expertise to get the project completed on time and on budget (he was really REALLY good), but by golly, was our boss angry the entire time.

When The Boss Is The Devil In The Details

, , , | Working | August 6, 2026

I remember having some direct reports being switched from a former boss to me. At the end of the first week, [Former Boss]’s people sent me everything they did all week in fifteen-minute increments. I am not kidding you.

Me: “What the h*** are you sending me all this for?”

Them: “We had to do it for [Former Boss] every Friday. He used it to keep track of us each day.”

Me: “How many hours a week are you spending on this report?”

Them: “Maybe three to four?”

Me: “That’s three to four hours that you could actually be spending doing your job and maybe clocking out earlier?”

Them: “Clocking out… early? I don’t understand.”

I told them that I trusted them to do what they needed to get done, and if they weren’t getting the job done, we’d have that conversation. But then I also had a life, and I wasn’t going to be remotely interested in what they were doing in fifteen-minute increments. That wasn’t my job. My job was to make sure the big picture was being done, and to help them do that.

Me: “I never realized that somebody could be that kind of an insane micromanager! Anything else he told you to do that I should know about?”

Them: “He used to shout at us for sitting down next to the printer when we were getting a large print job. We couldn’t walk away because the document was sensitive, so we had to stand there while two hundred pages would come out, but we weren’t allowed to sit.”

Me: “I think I know why [Former Boss] isn’t with the company anymore…”

Sadly, bosses who micromanage to this extent are usually people with a lot of anxiety, and they don’t realize that it is actually going to get them the opposite of what they want.

Meal With It

, , , , , , , | Working | CREDIT: welcomenal | August 6, 2026

My job pays a total of $35 per day for food while traveling, divided into breakfast, lunch, and dinner. The rules also say that each meal needs to be bought within certain time periods of two hours. You must eat breakfast between 8-10 AM, lunch between 12-2 PM, and dinner between 5-7 PM. They didn’t use to be too stringent about this because the person who approved travel expenses thought it was stupid.

Then they replaced her.

Because they would only approve a very cheap flight, I had to leave my home at 3 AM. I stopped to grab coffee and a bagel at about 5 AM. The new person rejected it and said I could only buy and eat food within a meal period.

Well, fine.

I used to work straight through lunch. Because I have to work with people from lots of time zones, this was sometimes necessary. Now I leave or reject calls because it’s in my lunch period and I must go lest I miss it.

No working late either. I leave at 5 PM because I can’t miss my dinner period. I also make sure to spend all $35. I must be healthy and not skip meals.

Coincidentally, hungry homeless people also enjoy my meal periods.