October 5, 2026 at 10:43 am

Employee Was Shocked When His Boss Denied A Coworker’s PTO After A Family Loss, So He Started Considering A New Job

by Benjamin Cottrell

bad boss throwing papers down

Pexels/Reddit

Sometimes it takes hearing what happens behind closed doors to realize just how badly a workplace has lost its way.

One employee had noticed his colleague acting unusually withdrawn and frustrated, but every attempt to ask what was wrong had been brushed aside.

Then the colleague suddenly disappeared from work for nearly two weeks, only to return looking as miserable as ever.

The explanation finally came out during drinks after work, when he’d had a few too many and admitted his family had suffered a devastating loss.

When the employee learned the horribly insensitive comment their boss had made in response to his colleague’s request for time off, he realized he needed to find somewhere else to work.

Keep reading for the full story.

My boss is a bad human

My colleague, a man in his late 30s, and his wife are living in two different cities, about 4 hours apart. Their respective industries are prevalent in those cities, and work from home is not an option for either.

So they live separately and commute every weekend. Both are extremely kind and helpful people, and deserve to be happy.

But recently this employee noticed quite a change in his demeanor.

Recently, my colleague seemed extra gloomy and frustrated. I asked him a few times what was wrong, but he just shrugged and said nothing.

A few days after that, he just didn’t show up to work unannounced.

The boss made it clear he wasn’t invested in the situation at all.

He didn’t pick up when either the boss or I reached out to him. He finally showed up on Thursday after almost two weeks.

To my surprise, our boss said nothing. I assumed they discussed it, and didn’t ask.

My birthday was on Thursday, and I invited my colleagues for drinks after work.

That’s when the employee finally learned the truth about what happened.

This guy came in the same grumpy state and had a few drinks too many. He then confided in me in his intoxicated state.

Apparently his wife recently lost the baby, and he wanted to take time off to be with her.

The boss then said something incredibly insensitive.

Our boss denied his request, stating, “The baby’s already gone, what’s the point now.”

But my colleague decided to put his wife above everything else, and even took a pay cut during this period.

The employee then decided he didn’t want to work for someone who said things like this.

We are in a country where labour laws are basically nonexistent, and being in the finance industry only makes it worse.

I am now trying to help him find another job, but I will quit too. No way I’m working for a man who lacks basic human compassion.

What a horrible boss — and person.

Redditors chime in with their thoughts.

This user wouldn’t let this boss’ indiscretion stay a secret.

Screenshot 2026 09 20 at 12.42.28 PM Employee Was Shocked When His Boss Denied A Coworkers PTO After A Family Loss, So He Started Considering A New Job

The quality of a boss can make or break a job.

Screenshot 2026 09 20 at 12.42.59 PM Employee Was Shocked When His Boss Denied A Coworkers PTO After A Family Loss, So He Started Considering A New Job

If you enjoyed this story, check out this post about a craft store customer who refuses to take no for an answer when it comes to wrapping his purchases for gifts.

This commenter doesn’t approve at all.

Screenshot 2026 09 20 at 12.43.09 PM Employee Was Shocked When His Boss Denied A Coworkers PTO After A Family Loss, So He Started Considering A New JobThis boss is clearly someone who had completely forgotten that employees are human beings with lives that don’t stop when they clock in.

His colleague really wasn’t even asking for that much. He simply wanted to stand beside his wife, and the response was mindblowingly tone deaf.

Grief is a human emotion, not an inconvenience to the company calendar.

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Benjamin Cottrell | Assistant Editor, Internet Culture

Benjamin Cottrell is an Assistant Editor and contributing writer at TwistedSifter, specializing in internet culture, viral social dynamics, and the moral complexities of online communities. He brings a highly analytical, editorial voice to his reporting on workplace conflicts, malicious compliance, and interpersonal drama, with a specific focus on nuanced stories that lack an obvious villain.

As a published author of rhetorical criticism, Benjamin leverages his academic background in human communication to dissect and elevate viral social media threads. Instead of simply summarizing events, he provides readers with balanced, deep-dive commentary into why the internet reacts the way it does. In addition to his cultural reporting, he is an experienced fine art photography essayist and video game reviewer.

When he isn’t analyzing the latest viral debates, Benjamin is usually chipping away at his extensive video game backlog, hunting down the best new restaurants, or out exploring the city with a camera in hand.

Connect with Benjamin on Instagram and read more of his essays on Substack.