Workers Share The Worst Times Bosses Have Refused Time Off

Two women in an office setting, one gesturing to a sheet of paper
Unsplash | Amy Hirschi

If you're lucky, you've had some cool bosses before. But more often than not, it feels like bosses have it in for their employees, vindictively punishing us when life gets in the way.

Since HR isn't our friend, and because we need to work to live, all we can really do is commiserate with each other. A Redditor shared their story of how their boss tried to get them to work on a day they'd requested off (for their own wedding), and it led it a lively discussion of terrible bosses.

A Redditor shared their story of getting personal time off for their wedding week rejected.

Woman's hands writing in a journal
Unsplash | Marissa Grootes

Redditor u/acidalia-planitia explained that even after requesting personal time off for their wedding week, they were still scheduled to work on the day of their wedding.

Turns out it was a scheduling mistake.

Man writing on board full of Post-it notes
Unsplash | Jo Szczepanska

In an edit, u/acidalia-planitia said, "It was a scheduling mistake, but still frustrating as this isn't the first time it's happened (was scheduled to work after requesting off for surgery in May.)"

Ultimately, it's good that things were ironed out, despite the frustration. The story led to thousands of commenters venting their frustrations with terrible bosses.

I couldn't have said it better myself.

Person playing chess

"Sounds like the person making schedules went on a power trip that's going to bite them in the ass when they're short-staffed after you prioritize your wedding over whatever job it is that has an insecure middle manager putting people on shifts they can't take as an act of aggression."


Ideally, personal time off should be approved with little fuss.

Two people with laptops speaking at a desk, in black and white
Unsplash | charlesdeluvio

"I just got promoted to management at my very large corporation and basically HR sits you down to start with and walks you through PTO and basically says basically under no circumstances should you deny PTO but it still needs to be approved.'"


Some bosses are on a nonstop power trip.

Man yelling into a landline phone
Unsplash | Icons8 Team

"I got written up for not attending the Christmas party over our days off, I had the flu. When I asked the CEO why she wrote me up she said, the rules do not give anyone a reason to miss the Christmas party. I asked her what if I died, she said, well, the rule says you have to attend or you get written up. This was a non-profit to help [domestic violence] victims and provide mental health treatment to those in Los Angeles. A few weeks later she fired an intern for getting pregnant. The intern sued and rightfully won."


"I'm not asking you, I'm telling you."

Man leaving an office
Unsplash | Jornada Produtora

"My current manager tried to tell me I couldn’t leave two hours early the day before my last vacation. I had to inform him I wasn’t asking permission, I was letting him know as a courtesy I was leaving early. This was a month ago. He’s still mad lol."

Again: sometimes you need to lay down the law.

Person gesturing with hands in a meeting
Unsplash | Headway

"'It wasn't a request' is something everyone needs to realize they can do, and should do. If it's something last minute, then sure — my bad, I'll try and get it sorted. But like something like a wedding that I've been planning for MONTHS, very publicly... I'm sorry, but you also have had months to plan for this. Ain't my problem that you didn't."


Seems like this is a popular strategy.

Two men standing and talking in a conference room
Unsplash | Muhammad Faiz Zulkeflee

"Boss, I just saw the schedule and see you have me on for x dates. I think you may have misunderstood, I was informing you the dates I am going to be gone. It was not a request. I will be available on Y date."


All's well that ends well.

Bride and groom holding hands
Unsplash | Jeremy Wong Weddings

"When we booked my wedding it was a year early and I remember telling my then boss I need these two weeks off for my wedding and honeymoon and they said 'at the moment we can’t process holiday for next year (fair enough case in most places I’ve worked at) but you’ll have to submit it at the beginning of the year in case someone else gets it, then you can’t have it.' I just stared at her and said, 'Okay I will submit it at the beginning of the year but I’m not asking for those two weeks, I’m telling you I’m not here., She didn’t know how to respond to that and I got those two weeks off."


Sounds like a good boss.

Two women talking over a white table
Unsplash | Christina @

"Mine straight up said she will never deny anything, she just needs me to email it to her for paper trail in case a higher higher up asks, and for me to add it to my meeting calendar (which is shared with team) since she's not going to remember.

She also reminds us frequently that we don't actually have to tell her why we're taking leave, and she isn't allowed to ask."


Technically the truth.

People gathered around a gravesite at a funeral
Unsplash | Rhodi Lopez

"My old boss tried to deny leave because I had used a lot of my leave the previous year. I lost both parents and had to deal with the estate and selling the house etc. I apologized to them that my folks had died, and promised that it would never happen again."


Sick days can be the ace up your sleeve.

Woman looking at phone while lying in bed, black and white
Unsplash | Sayo Garcia

"Same thing happened to me. Put in PTO at the beginning of the year for my son's first birthday next month and it was just declined due to staffing issues. I’ve been at my job for 1.5 years and never requested any other time off. Looks like I’m going to be sick that day."


It's usually a power trip, and they usually back down.

Two men in suits engaged in conversation
Unsplash | Sebastian Herrmann

"I had this situation for my honeymoon. I told them I had plane tickets set and everything. They tried to tell me that I should only buy tickets after being granted that time. There were absolutely no reason for them to deny it besides having a low pool to pick from which isn’t my problem. I gave proper of time ahead and followed all the rules and then not being able to retain people is not my problem.

So it came down to that they can grant it or I won’t be returning after my honeymoon. So they granted it."


If they want to play it by the book...

Workers in a large office
Unsplash | LYCS Architecture

"When you are presented with a documented discipline make sure to write in the comments that it is shameful/disgraceful for a company to deny PTO for a marriage. Immediately stop doing anything 'extra' and when questioned remind them of the treatment you received and that you're just reciprocating the relationship standards."


That's just soulless.

Man in a hoodie covering his face
Unsplash | Christian Erfurt

"I was fired for going to my wedding in 2010. I ended up in the hospital 3 weeks before. Had a positive stress test and they kept me 3 days. All was ok but work said because I missed those days I could only have my wedding day off. Not the week requested. We were traveling 900 miles to the destination and a few days for honeymoon. They sat me down and said I had to work. I told them straight up, I will NOT be here. They tried to get me to quit but I forced them to fire me. I took the unemployment for a year just to spite them."


They're either talking about a district manager or a dungeon master.

Two women speaking at a conference table
Unsplash | Amy Hirschi

"I just lost a great employee because my DM rejected the time off I submitted for her for literally no good reason at all. I had coverage for her shifts. It was no problem at all to accommodate her. DM declined it just because she could."


To the point.

A bride and groom smiling at each other inside a greenhouse
Unsplash | Samantha Gades

"You work to live, not live to work. Getting married is one of the most important moments in your life. What's the point of working if you can't enjoy the utmost important days of your life?

Tell them one more time you're not coming in during your wedding week, and enjoy your wedding."


Why do they even need an explanation?

An open planner
Unsplash | Eric Rothermel

"I worked with someone who, while filling out a time off sheet, asked what the empty space for notes was. I said 'if they decline, they'll put why on that section.' He responded 'I'm not asking for time off, I'm telling them I won't be here.' Since then, thats how I've treated time off, I'm not asking for time off, I'm giving you the benefit of letting you know, I won't be in. [A] wedding is more important than any job."


It doesn't need to be this complicated.

Two women in an office setting, one gesturing to a sheet of paper
Unsplash | Amy Hirschi

"I’m, like, a co-supervisor of a group and upper management was talking to us about PTO and how many people we’re allowed to have off at a time (which is understandable to an extent to make sure everything gets done without people staying late). But I said when it’s way in advance it’s not a request, they’re telling us, we can figure something out for that day, they got so uncomfortable lol it was hilarious."


Teamwork makes the dream work.

Four hands engaged in a four-way wrist-shake
Unsplash | krakenimages

"I am a supervisor at a small, private agency and I have NEVER denied the people I supervise their time off. You know what I do if we have limited coverage? I do their job AND mine. It’s not easy, but I get [it] done. And then when it’s my turn to be off, they cover for me. It’s called TEAM WORK."