40+ of the Most Embarrassing Office Party Fails Ever

One of the worst things that can happen to you in the office is having a bad boss. Your boss has enough power and influence that a bad one makes everything harder to deal with.

Imagine complaining about your boss within earshot of your kid, and then this slips out at the office Christmas party. We need to know what the boss’s reaction was to her little outburst. Hopefully, he’s a boss with a sense of humor!

Have you ever been chatting with someone and gone to pat their arm or their back, just for them to move and you accidentally touch them somewhere inappropriate? Or maybe you’ve accidentally hit them because of it.

It sounds like this guy has got some pretty poor reaction times. He should probably get his reflexes checked or his poor boss will keep suffering from accidental slaps. At least it gave everyone at the office party something to talk about.

Let’s throw it back to the early 2000s. The Hills was on TV, girls were layering their lacy tank tops like there was no tomorrow, and everyone was obsessed with spray tans.

Flash forward to 2016 — when someone actually thought a can of spray tan was a good gift, and the one person who definitely didn’t need it was the one who got it. We bet he threw that can back in 2006 where it belonged.

Office parties mean people bringing their partners, and people bringing their partners means strangers at the office. But, strangers at the office doesn’t mean that you can just start flirting with them willy-nilly.

You have to assume that the person you’re talking to was brought by someone they’re in a relationship with, so be careful with that liquid courage and bottle it up for another occasion, or you’ll end up flirting with the boss’s wife — like this guy did!

Have you ever been sitting at your desk and been struck with the urge to get up on it, and dance or shout about how much you hate your job? Well, the office holiday party is the perfect time to do it!

No one will bat an eye, because it probably isn’t even the craziest thing they’ve seen that evening. What is crazy, though, is watching your boss epically fail at a trust fall. Guess they weren’t well-liked.

Ugly Christmas sweaters are a pretty weird phenomenon. Something that originally started as a clothing item not intended to be ugly but widely mocked became a holiday party trend. So much so, in fact, that some people even buy ugly Halloween sweaters now.

What’s not pleasant is being told your sweater is ugly when you definitely didn’t intend for it to be. Did the award at least come with some adult beverages for this person to drown their sorrows a little?

Pizza is one of those foods that you can finish off on your own. You only share it because you feel like you have to. So, imagine having to share two pizzas between 15 people.

And to make matters worse, your boss decides to eat one entirely on her own, leaving only one pizza for 14 people! It sounds like her boss is a very selfish person, or was just extremely hungry. She better have ordered another pizza afterward.

A lot of offices straight up refuse to have adult beverages at office parties, and you can’t really blame them. People struggle to control themselves and get very silly very quickly, causing all sorts of chaos.

But, then there are those employees who are so clumsy that they wreak havoc without even trying, like this poor woman. She went straight to the store afterward and demanded a refund on those faulty high heels — at least, that’s what she should have done.

Relationships fail. It’s just an inevitability. Sometimes, we are too different to make it work — other times, the relationship is toxic and unhealthy. And one of the worst things you can do as a friend is start dating the other person’s ex.

But our bosses aren’t our friends, so they apparently have no problems jumping into a relationship with our exes, like poor Tim here learned at the office party. This probably wasn’t the first time the boss man had done this.

Let’s be honest — no one actually enjoys office Secret Santa gift exchanges. You end up buying people small items that they simply don’t need, and usually don’t even want. So, when this employee was forced to participate, he decided to have a sense of humor.

This was honestly probably the most useful gift out of the ones given in the office that day! That person had a week or two of tasty cucumber salads and cucumber water.

Sometimes, an office party means enjoying things you liked when you were a kid. That may mean dancing on your desk, or it could mean playing hide-and-seek with all of your coworkers.

This guy is the king of hide-and-seek! How did he even get up there in the first place? We have so many questions, but mostly we’re just impressed with his hiding skills. He must have had a hard time not giggling as they wandered around confused.

Everyone who’s looking for a partner in life wants someone who understands them and appreciates them exactly as they are. But, even the best of partners can be embarrassed by adult-beverage-induced antics, like this girlfriend clearly was.

He was probably falling over while he asked her this, and she was trying not to grimace as she answered, mortified by his behavior. Let’s hope for his sake that she was just kidding and that he didn’t lose more than his dignity that night.

Ah, the office printer and copier. It’s the one place in the office that puts everyone on an equal playing field, as they’re all equally confused about how to use the darn thing in the first place.

This isn’t an office party fail, this is an office party win. It’s hilarious, it’s clever, and it probably took him a lot of time to do. This sounds like something straight out of an episode of The Office.

Some offices just don’t have a good environment, no matter how hard some working there may try. It could be because of a toxic boss, or that the employees have very different personalities and just don’t get along in that way.

If you have to make an office party mandatory to get employees to attend, maybe you just shouldn’t throw one. The whole point is to reward employees, but they clearly don’t want to go, which points to some bad office politics.

Although it’s hard to believe for many of us, there are people out there with cellars full of expensive bottles of various drinks. Some like to collect them, and others keep them for very special occasions.

The boss probably wouldn’t consider an office Christmas party a special occasion for using a $10,000 bottle. But, why did the boss leave such an expensive bottle somewhere where a coworker could find it so easily?

Do you struggle to reach the higher shelves in your kitchen and need to use a step stool? Do people constantly offer to help you get something up high at the grocery store? If you answered yes, odds are you’re a short person.

Odds are even higher that you’ve been mistaken for a kid or a teenager at least once in your adult life, like Kate here experienced at the office Christmas party. You just have to shrug it off.

When certain types of beverages, or “fun in a cup” are involved in office parties, things can go from fun to sour very quickly. It also tends to bring out the emotional side in people, including your boss.

This is really sad and also must have been so uncomfortable for the employee. If she and her boss weren’t exactly close, we bet things were very awkward when everyone returned to the office post holidays!

No matter how much you enjoy your job, you must just not want to go to an office party. You’re tired, you have other things to do, or you just don’t like your coworkers enough to spend time with them outside of work.

Not going may be the right choice for some, but it seems it wasn’t for this employee. They better have at least saved her a gift card while she was in the emergency room dealing with her broken toes.

A classic sign of having had one too many fun drinks is struggling to see things clearly. Sometimes, your vision blurs so much that you mistake rubber Christmas trees for beautiful women.

Oh, it’s never happened to you? Well, that must mean that you just haven’t had enough fun drinks before, which is probably a good thing. Then, you won’t embarrass yourself at the office party as badly as this boss did.

While most people think of Christmas when they think of an office party, some offices celebrate other holidays, like Halloween. But, just because there’s a Halloween party doesn’t mean there are costumes.

Poor Alex here learned that the hard way after experiencing a little bit of good-natured hazing from a coworker. We wonder if they started dressing up after this incident to make Alex feel better (they probably didn’t, but at least they all had a good laugh).

Tying a cherry stem in your mouth is a common old-school party trick. Everyone probably has different ways of doing it, although a common one is using the roof of your mouth to hold it still and straight.

However, if you get it a bit too far back, it can be a bit of a choking hazard, as this poor girl found out. The IT guy probably would have been more impressed if she actually knew how to use her computer properly, which she probably doesn’t.

There’s something about photo booths that make you feel like a little kid again, especially when there are props involved. Maybe that’s why they’ve become popular at so many weddings and office parties nowadays.

This sounds like a decision fueled by one too many adult beverages, and one that girl is definitely going to regret since it seems no one filtered the photo booth pictures before uploading them to Facebook! We have to wonder if she got fired for that.

There’s a certain red-or-white adult beverage that many people love, and if one thing is for sure, it’s that it’s made with grapes — not apples. These office employees didn’t seem to know that, though.

This sounds really fishy. How did no one realize that it was actually apple juice, and why would they act under the influence? It’s also just mean on the boss’s part to trick their employees like that.

Have you ever seen a scene in a movie or TV show where someone shows up dressed just like the wait staff that the caterer brought to the party? Well, it turns out that actually does happen in real life.

This is just really bad luck, but he could have taken advantage of the situation by messing with his coworkers a bit. It’s sad that one of his colleagues didn’t recognize him as a fellow employee.

Big glass doors and windows are the worst. If they’re kept clean and in a spot where the light hits them just right, it’s so easy to believe that there’s nothing there at all.

This person learned that the hard way multiple times. We wonder if they’d had a few fun drinks to make this mistake multiple times, or if they just have a really bad memory. Either way, at least it was entertaining for everyone else to watch.

When you’re walking around in a place like Walmart, there are a lot of little gadgets in the aisles that make you say, “Ah, that’s clever.” But, you’d never buy them because there’s just no point in owning one.

A banana protector is one of those items. Its peel already protects it, and if you’re worried about it getting all over your bag, it’s probably too mushy to take with you. We aren’t surprised this made its rounds at the office.

Sometimes, things at the office party get steamy. Everyone has a few adult beverages, and next thing you know, those two coworkers that have spent months flirting with each other suddenly disappear.

Why would someone be filming what’s going on behind the conference stage at an office party? This one sounds a bit fishy to us. On stage, sure, but behind stage? It’s like they wanted to catch employees doing something!

There are a small minority of employees out there who are lucky enough to have a really great boss. They feel comfortable joking around with them, and even making fun of them at the office party — like Ella did.

So, she went through the effort to get a photo of her boss and have it printed on a sweater? She must really trust her boss’s sense of humor. We hope she took it off and gave it to the boss afterward.

Unfortunately, no matter how hard you work to get people to like you, there will always be people who don’t. But, it’s even more unfortunate when those who don’t like you are your own coworkers.

It’s pretty rude to throw an office party and leave employees out of it, especially if the party is actually taking place at the office. Don’t take it too personally, Jon. They just don’t sound like nice people.

Considering the majority of people we know have hair, we’re all eternally fascinated by bald people. There’s just something about a head with no hair that’s fascinating, especially if you’ve had one too many beverages.

Most bald people probably wouldn’t appreciate having their head used as a crystal ball, but this boss didn’t seem to mind. We aren’t sure how accurate fortunes coming out of a head would be, though.

There’s a reason that most holiday parties at the office are held on a Friday evening. If there are adult beverages involved, people need time to recover from one too many of them and whatever poor decisions they’ve made.

So, having a party on a Monday is just begging for trouble, and it’s not surprising that everyone called out sick the next day! Let’s hope there wasn’t any urgent work that needed to be done.

Holidays aren’t the only things that spur office parties. Sometimes, there are other special events — like celebrating the retirement of someone who’s worked for the company for a long time, like Peter.

This isn’t the first story like this, and it really makes you wonder whether cake decorators are paying any attention to what they’re writing on their cakes! But the good thing is that Peter’s cake was unique, not just a boring, run-of-the-mill sheet cake.

The office refrigerator is a scary place. It’s a place where food sits too long, where sandwich thefts happen on a regular basis, and where germs thrive because no one ever actually cleans it.

One has to wonder why Lauren here had meals sitting in the fridge not being eaten for that long. She must be one of those people who brings food with her just to go out for lunch anyway.

Short cruises and food just seem like two things that shouldn’t go together. People aren’t on the boat long enough to get over their seasickness like on a normal cruise, so you end up with some bad situations, like this one.

Throw in stormy weather, which means churning seas, and it’s a recipe for disaster. At least if people actually got sick, they could just lean over the railing instead of crowding into a bathroom!

One of the hardest parts of giving gifts is making sure that the person actually wants and likes what you’re going to give them. Everyone’s tastes are so different that it can be hard to know what will be well received.

To be fair, unless the sweater that the coworker gave her was truly hideous, it was a poor decision to wear it to an ugly sweater party. It’s like she was trying to insult the person who gave it to her.

Picture this — you’re at the office Christmas party and load up a paper plate with tons of delicious food, find the perfect spot to sit and eat, and then realize you didn’t grab a drink.

You put your plate on your seat and come back with your drink, just to sit right in your food like both Mark and his girlfriend did. Now you’ve got no food, a dirty outfit, and a whole lot of embarrassment.

A Chinese gift exchange — also known as Yankee Swap — is when someone chooses a random gift, and then the next person can either steal that gift or choose an unopened one until all gifts are opened.

It means that the people going first usually end up with the worst presents, but whether a reindeer poop ornament is the worst or best present is a matter of perspective. It’s funny and memorable.

The best kind of ugly Christmas sweaters are the ones that are more than just sweaters. There are Christmas trees with tiny little LED lights, and Santa sweaters that say “Ho ho ho!” when you push a button.

It’s a shame that her sweater was damaged, but you have to admit that this would have made a pretty hilarious talking point at the office party. There’s nothing funnier than the voices of toys running out of battery.

It’s bad enough to leave employees out of an office party, but to not invite the boss is a pretty bold move. It says, “We really don’t like you and don’t want you around.”

If the boss doesn’t find out, then it’s not a big deal. If they do, though, then you’re going to have a few really awkward weeks around the office, which these employees definitely did. The question is, did any of them get punished for it?

Karaoke is both the best and the worst. It’s so much fun and anyone can do it, but the problem is also that anyone can do it, including people who are horrible singers and painful to listen to.

This boss probably sucked at singing so they decided to be the guitar instead. He didn’t fall over, he just played air guitar very dramatically! There are competitions for playing air guitar convincingly, and he probably could have won.

When we’re stressed out at work, sometimes all we want to do is crawl under our desks and hide. It seems like such a nice, cozy, secluded place to be. That’s definitely what these two coworkers thought.

We can’t say we’d be that upset about them hiding under the desk, but the vomit would definitely be upsetting. Did Jordan show up to work the next day with a carpet cleaning kit for his coworkers?

We all generally regard the owner of a business as a big ol’ Mr. Money Bags. They’re the big boss, the one who calls all the shots and makes all the deals. So, you’d think that the least they could do is splash out on a Starbucks gift card for Secret Santa.

That wasn’t the case here, though. Did he at least put new batteries in the flashlight, or did he just give them a used flashlight that doesn’t even work?

At the end of the day, no matter how much we enjoy our jobs, we’re there for the paycheck. If we didn’t need paychecks, most of us probably wouldn’t work. So, employees really look forward to receiving a Christmas bonus for a job well done.

A copy of Elf, whether defective or not, is simply not a good replacement for a Christmas bonus. Nothing is a good replacement for a Christmas bonus, really.

Pet owners don’t understand how much their pet’s hair permeates everything in their home. Aside from the obvious clothes and furniture, it turns up in drinks — or in this case, even in the food.

As much as she wanted to contribute to the potluck, if the food she was bringing was covered in cat hair, it probably would have been better not to bring it at all. No one is going to sit and pick off cat hairs so that they can try your caramels.

Office raffles are often a waste of time. No one wants a basket full of chocolate that badly. But sometimes, offices give away a present people would actually use, like a free hotel stay for two.

Who’s to say that she wasn’t going to have a nice mini getaway with her friend or her mom? Who’s to say she even wants a man at all? It was so inappropriate for her boss to say something like that, especially in front of others.