September 17, 2025 at 11:35 am

His Boss Wanted To Know Why He Was Requesting Time Off, So He Made Up A Sob Story Just To Watch His Boss’s Reaction

by Jayne Elliott

businessman with his hands behind his head

Shutterstock/Reddit

When you want to take a vacation, a sick day, or just enjoy a day away from work, it’s important to let your employer know, but what would you do if your boss asked why you wanted the time off?

Would you be honest, refuse to give details or add a little embellishment to the story?

In today’s story, one employee decides that if his boss wants to know why he wants time off he’s going to make the reason a good one…even if it’s not true.

Let’s see what he told his boss.

You want me to provide a good reason for why I want to use my vacation days? Time to trauma dump

So I work in a pretty low stress job, which makes it absolutely hilarious that my boss demands that whenever we take our paid time off we “give a good reason”

Like, dude, why do I need to give you a good reason to take my vacation days? They’re mine, I’m entitled to take them to dedicate the time to my new hobby of staring at the ceiling, it ain’t none of your business.

Well I had planned to take a few days off to recharge after a (very relatively) intense work week.

If the boss wanted a reason, he’d get a reason!

Unfortunately the boss thought this was a great time to send out a “reminder” email that if we intend to take time off we need to provide a reason & have it approved.

This was a mistake on his part.

I went into his office, head hanging low, and started talking about my dad’s cancer, how intensive chemotherapy was, I didn’t make myself cry but I was putting that theatre class I took in college to good use, I might have even hit him with “and I’m just so used to seeing my dad as this strong, invulnerable guy, but… he’s just human, y’know? And soon he might be gone… how do you even deal with something like that…”

The boss still didn’t change the policy.

Now by this point my dad had been cancer-free for years, so this was purely performative, but my boss just looked so uncomfortable, it was great.

I wish I could say this caused the boss to send out an email saying we no longer needed to give a reason for our time off, but no such luck. Instead I just kept coming up with other traumatic life experiences to justify my vacations.

I think my grandma died 3 times these past few years, poor woman. I may have to come up with something new for when she actually does die.

My boss still gets visibility uncomfortable whenever I come to ask for time off in person instead of via email, it’s kind of hilarious to me.

What a ridiculous policy. You shouldn’t have to explain why you want to take your vacation days, but I like that OP made it dramatic.

Let’s see how Reddit reacted to this story.

This person would point to the benefits package.

Screenshot 2025 07 15 at 11.56.36 PM His Boss Wanted To Know Why He Was Requesting Time Off, So He Made Up A Sob Story Just To Watch His Bosss Reaction

This person would pull out the employee manual.

Screenshot 2025 07 15 at 11.57.24 PM His Boss Wanted To Know Why He Was Requesting Time Off, So He Made Up A Sob Story Just To Watch His Bosss Reaction

Another person states that it’s not a request, it’s a warning.

Screenshot 2025 07 15 at 11.57.45 PM His Boss Wanted To Know Why He Was Requesting Time Off, So He Made Up A Sob Story Just To Watch His Bosss Reaction

Here’s a suggestion to have some fun with the sick days too.

Screenshot 2025 07 15 at 11.58.00 PM His Boss Wanted To Know Why He Was Requesting Time Off, So He Made Up A Sob Story Just To Watch His Bosss Reaction

Don’t ask for details if you don’t want to feel uncomfortable.

If you liked this post, check out this story about an employee who got revenge on a co-worker who kept grading their work suspiciously low.