• From telling fat people not to order salads to posing for a picture on a dating app, the
Planet Dolan crew re-enact some of the best true stories from our subreddit about the
dumbest things our bosses told us to do.
I’m Pringle and today I’ll be your narrator.
Number 10 was submitted by Queenofcats123 Tolop
When Tolop worked at a grocery store, her boss told her to clean the toilets.
Not very weird, but the way he wanted her to do it was very weird.
He told her to use a mop and a gallon of expired milk to scrub the floors.
So, Tolop’s boss gave her a tub of expired milk and a mop, then told her to put green
food coloring in it to make it look like cleaner in case someone saw her.
Tolop did what she was told, and her boss told her that it was top secret and not to
tell anyone.
Number 9 was submitted by Princess_Shireen Spincess
One time, Spincess worked at a fast food restaurant.
One of the managers got mad at her for taking an obese customer’s order for a salad.
In a rude tone, her manager told her to discourage any obese customers from ordering salads because
they were demeaning themselves by eating healthy.
Spincess didn’t know what the fuck that was supposed to mean, so she continued to
honor the obese customers’ requests for salads.
Another incident had the same manager tell her to sweep the entire parking lot using
a small broom and a dustpan.
Not only did Spincess have to sweep up the trash, which was reasonable, but also had
to pick up EVERY leaf!
It was embarrassing, since people who drove by could see her.
Her manager would even come out sometimes and laugh at her.
Two months later, Spincess got sick of it and quit.
Number 8 was submitted by Just_narcissist001 SaltySquid
When SaltySquid worked at a supermarket, his manager had a weird thing about gay guys.
She wasn’t homophobic, but though that all guys were secretly gay for each other.
One day, she asked SaltySquid and one of his coworkers to come to her office.
She asked them a bunch of personal questions, trying to get them to confess their love for
each other.
SaltySquid and his co-worker worked well together, but didn’t know each other outside of work.
When their manager began telling them that there was a strict “no inner-relationship
policy” that they had to follow, SaltySquid and his co-worker laughed.
They tried telling her that they weren’t gay, but that wasn’t good enough.
She needed proof, so she told them to kiss each other, and she would judge if there was
any kind of relationship.
Instead, they stood up, walked out of the store, and never looked back.
She was eventually fired for trying that same stunt on several other people.
Number 7 was submitted by 051R15_Da_Virus Cidius
One time, Cid worked as a suspension technician at an automotive company.
His boss was taking some vacation time to attend his daughter’s wedding.
It was a catered event, with a musical act set to perform.
However, the person who was supposed to perform didn’t show up.
Panicked, Cid’s boss called the company and ordered him to come to the wedding and
fill in for the singer immediately.
Cid went to the address that his boss gave him to sing, since he threatened to dock his
pay if he didn’t show up.
He arrived just as the music was about to begin.
Cid was nervous, since he had no time to prepare or change out of the company’s uniform.
After being put on stage and told to sing acapella, Cid decided to sing Frank Sinatra’s
“My Way.”
To his surprise, everyone loved it… including his boss, who gave him a bonus.
Number 6 was submitted by kingyacooobtheholy Hellbent
The dumbest thing Hellbent’s boss ever told him and his co-workers to do was on a very
cold but sunny day in March.
His boss was having a birthday party and invited all his employees.
It was going well until the drunk boss stood up, grabbed a microphone, and ordered everyone
to pull down their pants and run around outside.
Hellbent and his co-workers knew that their boss was a weird guy who often liked to joke
around.
That time, though, he was serious and even threatened to fire anyone who didn’t obey.
So, Hellbent and his co-workers pulled down their pants and ran around in the very cold
weather.
Number 5 was submitted by YummiestDonut Princess Proton
When Princess Proton worked at McDonald’s, her boss told her and her other female co-workers
to go into the freezer in only their undergarments.
Her boss made them do that so he could get turned on while watching the cameras.
Princess Proton quit after he asked her to do that, and almost immediately got a new
job working the counter at a grocery store.
Number 4 was submitted by whathappendtome33333 Doopie
Doopie was called into her boss’s office one day.
Her boss had been acting very weird, but she still went in because she didn’t want to
get fired.
Her boss told her to sit on her desk, and she obeyed.
That was when Doopie noticed that her boss had a dating app on her phone, and wanted
to take a picture of Doopie and pretend that it was her.
It was because she thought Doopie was the prettiest girl in the office.
So her boss snapped the picture, then ended up dating an ugly man from the app.
Doopie, meanwhile, quit her job.
Number 3 was submitted by 4Corry Derek
Derek worked in the plant department at Home Depot.
One day, his boss told him to lick the mint plants to make sure they were fresh.
He promised a hefty bonus for each plant that he licked.
Although Derek sometimes licked bad mint plants that made him puke, he still thought it was
worth it in the end when he got paid his hefty bonus.
Number 2 was submitted by ExtermiNate900 Legna
Legna worked at McDonald’s so he could save up for a new computer.
One night, his boss came in drunk with puke on his shirt.
He started yelling at everyone, telling them to make him a double cheeseburger or they’ll
be fired.
He then told Legna that if he got him more beer, he would give him a raise.
If he didn’t, then he would have to clean up his puke outside.
The boss gave Legna his ID, somehow believing that the clerk at the liquor store would see
it and not realize that Legna was only 17.
So, he went to the nearest liquor store and bought a box of Bud Light.
The shop clerk asked, “How old are you?”
Legna showed the clerk his boss’s ID… and it worked!
The clerk let him leave the store with the beer.
When he got back to the restaurant, he saw his boss passed out in one of the booths.
Legna gave him the beer, but he said, “Bud Light?
I don’t like this shit!”
He then threw it out the window, with the case landing on someone’s car and denting
the hood.
The person who owned the car called the police, who came and arrested Legna’s boss.
After his boss went to jail, the restaurant closed and became a KFC.
Number 1 was submitted by tooktheheart Melissa
The place where Melissa used to work received a letter from an attorney related to a lawsuit.
Her boss ended up with the task of resolving and replying to the letter.
The big boss told her to handle it, so she handled it by handing it to Melissa.
Melissa was instructed to call the customer every hour on the hour, use a fake name each
time under a fake company if the customer did answer, then reply to the attorney that
the customer never answered and that they did their best to resolve it on their end.
She was also instructed to fake outgoing e-mail messages to make it seem like the customer
never replied to them.
She wasn’t given the full details but took on the task, only calling the customer twice.
They didn’t answer, but when the day was over, Melissa started to feel horrible.
She had no idea what she was doing, and after looking over the attorney’s letter, she
felt like she was going to get into serious trouble if she proceeded.
So, Melissa told her boss that she wouldn’t do it.
Her boss replied by telling her to grow a backbone, so Melissa went to the big boss
about it.
She told the big boss that she wasn’t comfortable, as well as what her boss had said.
Her boss ended up getting reprimanded, and a company meeting was held about better communication
and ensuring tasks are done properly.
Melissa’s boss held a separate staff meeting, saying that if anything ever made them feel
uncomfortable to let her know.
The company went out of business a year later due to poor management.
Huge thanks for the folks over on our Planet Dolan subreddit for submitting their stories.
We have another question for you: “What’s the dumbest thing you’ve ever seen people
fight over?”
Let us know in the reddit page linked below and you might be featured in a future countdown.