People Are Sharing Their Stories About Their Weirdest Bosses

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Have you ever had a weird boss? If you take into account the number of jobs most people have these days (it is a miracle if you are at the same company for more than five years) and the number of weird people that exist, chances are pretty good that you have worked for some real characters. It is just math, folks. I know I have worked for my fair share of crazy people. I once had a boss who forbade her employees from “fraternizing” outside of work, like she had that kind of power or something. She probably tried to enforce that policy because she knew that anytime my co-workers and I got together, we would talk about how horrible she was.

Strap in folks, because the people of Twitter came out in droves to share the weirdest stories about bosses that they have. And a lot of them are way weirder than mine.

Nicole Cliffe is the best at asking questions on Twitter.

She always gets people to share their best stories. This thread truly requires a spot on the couch and a bowl of popcorn to appreciate fully.

Hot dogs

This is insane and amazing, and it is extra amazing because hot dogs are probably the food that most resemble fingers.

Microwaved Pepsi

I have so many questions. Who microwaves soda? Who wants warm soda? And who chooses Pepsi over literally any other soda?

Perhaps you’ve heard

What a way to start a conversation! Also, this woman (the one who clawed her ex-husband’s eyes out) is now my hero.


Oh man the inefficient processes I have been forced to adopt over the years make me nuts. It’s always because older people don’t understand technology.


I mean, that is a special kind of paranoid, but at least this boss was looking out for their employees.

Two jobs

She clarifies in subsequent tweets that it was, in fact, two full-time jobs, and he kept up this charade for at least a year-and-a-half.

Punted mums

I guess punting bouquets of flowers isn’t something you’re supposed to do when you work at Home Depot’s garden center. Who knew?


This is so many kinds of unacceptable I really have no words for this. This is no kind of task to assign to your hourly receptionist.


Sure, you can just “get” an elephant. Man, in case you needed any more evidence that conservatives are insane.

Frosted tips

Um, yeah, unless you are like, a model or something, it is not OK to demand that your employees give you a “heads up” when they are going to change their appearances.

Called mom

Wow. This crosses all the lines.


This is insane? Obsessive? So so weird? Did this guy not have a life outside the store?

Gummy frogs

This is really endearing! And those gummy frogs are delicious.

White male boss

This is horrifying beyond belief but also somehow not at all surprising. White men are monsters.

Company time

Ooh I hate this so much! This is so illogical. If you need your employee to learn a specific skill, teach them! During the work day!

Locked in the freezer

Um, what?! This is abuse– no doubt about it.

Giant tortoise

Um, first of all, who is gifted a giant tortoise? What does one do with a giant tortoise?

Erotic romance novel

As a boss, it is fine if you are writing erotic romance on the side. As a boss, it is decidedly not OK to read your erotic romance to your employees.

So stupid

This is actually crazy. I feel like this is an unhinged Cecily Strong character from SNL. How is this a real person?

Wow, this is a pair of total characters. I’m kind of into rating my boss’ online dates, though. That would be fun.

Jumbo paper clips

Honestly, I understand. Jumbo paper clips are way better.

Fired a customer

Wow. This really is next-level.

Marriage question

How incredibly rude! I can’t imagine a boss who thought this was an appropriate question acts appropriately the rest of the time.

Dog the Bounty Hunter

The Jesus thing is terrible, but the Dog the Bounty Hunter thing is wild. So out there.


These are all amazing. I wonder if this is the same boss or three different bosses.


I have a lot of celiac disease in my family, and I can tell you without a doubt that this is not how it works.

Bill Clinton

Um, what? You know what? On second thought, I don’t want to know.

Personal errands

You know, I wish I could pay someone to go clean out my closet. Someday…

Broken bulb

I guess this is what it’s like working for the Incredible Hulk. Share this with someone and share your own weird boss story!