45 Office Party Fails That Make Us Want To Work From Home Forever

By Abigail T

It’s time for another list of highlights from one of Jimmy Fallon’s famous #Hashtags segments! The Tonight Show host is known for taking to Twitter and asking his followers to share their embarrassing and awkward stories and tag them with the hashtag theme of that week. Some of these hashtags even manage to make it to the Twitter Trending Topics nationwide! Jimmy then reads out some of the funniest tweets on the #Hashtags segment on his show. Let’s look at what people submitted for #OfficePartyFails, where people share their most remarkable office party mishaps and awkward moments. From unexpected exes to broken heels, here are some of the best #OfficePartyFails. Beware: lots of awkward, cringe-worthy, secondhand embarrassment-inducing situations ahead. Consider yourself warned!


This is not a very nice thing to do to your coworker, so we can only assume this was some kind of hazing process that @AlKikuyama had to go through. Some workplaces encourage their workers to dress up for Halloween, so Alex was just trying to fit in.

Tweet courtesy of Twitter/@AlKikuyama; Photo by Alexander Jawfox on Unsplash

Is anyone else reminded of that episode of Modern Family where the same thing happened to Mitchell? We wonder what this guy came dressed as on that first Halloween in that office. A Spiderman suit, maybe? Or did he go all out and went as Dracula with the bloody fangs?

Placebo effect

What started as mildly funny became even more of a joke at @iJharana’s office party. Events like this usually involve a lot of alcohol, but her boss decided to change that. You would think people would notice that it wasn’t wine in the wine bottles.

Tweet courtesy of Twitter/@iJharana; Photo by Katrin Hauf

As it turns out, grown-ups can be a little childish too! Guess nobody wanted to call the boss out for not providing alcohol at the party, so what did they do? They pretended to be drunk. But what if they only felt drunk as a result of placebo?

Slap gone wrong

It is possible to give someone a friendly slap. Just a gentle tap on the back or the shoulders, let them know you’re there or that they’re doing a good job. It is also possible for said slap to go awry. We’ll let @MilesRocks108 explain.

Tweet courtesy of Twitter/@MilesRocks108; Photo by Andrew Le on Unsplash

Yikes! It’s bad enough that he ended up slapping someone, period. But the fact that he smacked one of his managers across the face makes things just a tiny bit worse. We hope that slap didn’t result in him getting fired!

Trying to fit in

As it is during any social situation, all anyone wants to do is to fit in. You don’t need the people you work with five days a week to be thinking anything bad about you. So you do what they do, even though you’ve never done it before.

Tweet courtesy of Twitter/@CAgirlinDCworld; Photo by Daniel Santiagø

We’re getting a little sick from reading this tweet. Of course, it isn’t @CAgirlinDCworld’s fault. She just didn’t get that you just eat the insides of edamame because she’d never eaten it before. We wonder if anyone saw her eating the chewed skins…

Office party win

We don’t know why this tweet was tagged with #OfficePartyFail when this man just won the entire party! The only ones who failed were the coworkers who didn’t find this guy during this game of hide and seek. Maybe the poster lost early in the game.

Tweet courtesy of Twitter/@FroHorner

We do have one question, though—how did that guy get up there? There’s no ladder, no steps, no rope to climb up. Did he… did he fly? Is there something he’s not telling us? And how is nobody else asking these questions?

That’s kinda sad

You can tell the kind of work environment an office has by the number of people who show up to the office party. People will gladly attend a party at an office with a positive, affirming work environment and good management.

Tweet courtesy of Twitter/@Skyblumelon; Photo by Adolfo Félix on Unsplash

On the other hand, workers at @Skyblumelon’s office might not be too thrilled to be working there. They can’t be bothered to attend the office party, even when it’s made mandatory (which also says a lot). That is kinda sad and truly an #OfficePartyFail.

Missed out

There are a plethora of reasons why one would decide to skip the annual office party. You could be busy that night. You could just not like where you work. Or you could be feeling a little run down and not want to socialize. That’s completely fine.

Tweet courtesy of Twitter/@KasiaEmerald; Photo by Christian Wiediger

Unfortunately for @KasiaEmerald, whatever her reason was for not going, she completely missed out on $300. And to top it all off, she injured herself. Bet she regretted not showing up! She probably lost $300 paying for treatment of the toe injury instead.

Dress code

Party dress codes are always tricky. You want to look nice. You don’t want to overdress or underdress for the shindig, so you have to find that suitable in-between. And you don’t want to dress the same as the wait staff.

Tweet courtesy of Twitter/@Every1SayIMBoss; Photo courtesy of CHUTTERSNAP on Unsplash

This guy could have upstaged the party host, and he still would have made a better fashion decision than a red shirt and black tie. Safe to say, the rest of the evening was a little less than thrilling as people kept mistaking him for a waiter!

Third time’s the charm

You would think that you know your workplace inside and out. You learn to avoid the first-floor bathroom because it always stinks. You know which hours the office supply closet is empty so you can take a little nap, and you definitely know all the exits.

Tweet courtesy of Twitter/@badashfan75

And you definitely would know that there are sliding doors in the building. We’re guessing that @badashfan75 here got a little too much alcohol in their system, or maybe need new glasses. Sliding doors can start to get confusing the more drinks you down!

Ugly sweater party

Don’t you just love ugly sweater parties? Over Christmas, you would wear oversized ugly jumpers unironically. But at an ugly sweater party, there is an actual reason for it. We think this Twitter user has found the ultimate ugly sweater to wear to a party.

Tweet courtesy of Twitter/@ellalalalalara

Of course, this is a risky move on Ella’s part because you never know how the boss will take the joke. She could very well get fired for this, or at least deeply offend her superior. But maybe it was worth it.

Yearbook superlatives

As you grow older and step into the world of office work, you will realize that high school truly never ends. There are still bullies, inconsiderate authorities to please, and people still put each other in boxes. And you still get voted “most likely to…”

Tweet courtesy of Twitter/@lauren_light; Photo by Kate Trifo

Maybe the yearbook superlative given to this Twitter user was based on truth. Perhaps she does usually leave food in the communal fridge too long. Maybe it’s entirely presumptuous. But at least she got a free Tupperware out of it!

The boss’s FOMO

We’re a little confused as to how this next office party fail could even have happened. Twitter user @LeahBale15 and her coworkers threw an office party without inviting the boss. If this was the case, who paid for the party?

Tweet courtesy of Twitter/@LeahBale15; Photo by Roland Samuel on Unsplash

Maybe all the workers chipped in, or maybe Sheila in the financial department saw there was enough in the budget and went ahead and paid from the company account. Either way, it ended up in everyone getting yelled at because the boss had major FOMO.

Trust issues

Oh no. This next office party fail just created some deeply-rooted company issues. What happens when you do a trust fall in a room full of friends, and no one catches you? Well, you wouldn’t trust anyone after that, would you?

Tweet courtesy of Twitter/@whoopiepie10

Poor boss was probably having the time of his life and being so proud of the people he worked with for another successful year. Who would have thought that they would prove they didn’t have his back? Trust issues unlocked.

Pizza party for one

Some bosses are just stingy, although they try to pass it off as being frugal. The same can be said for @mseric’s boss, who ordered two pizzas for a party of 15. That only gives each person one slice of pizza to eat.

Tweet courtesy of Twitter/@mseric; Photo by Jordon Kaplan on Unsplash

Even worse, she ate an entire box by herself! Which meant her employees had to share a slice of pizza even to make the box go around. What kind of party is this, where even the food is rationed? We hope the employees went out on their own afterward!

Participating in protest

Secret Santa and White Elephant gift budget limits can be a sensitive subject for some people. If you set the limit too low, it could annoy some people. If you set the maximum too high, it could stress someone out.

Tweet courtesy of Twitter/@kingedhell

Clearly, for this guy, it was a touchy subject. Maybe he didn’t even like his coworkers and didn’t want to participate in gift-giving. But alas, if the Secret Santa exchange was mandatory, he would have given the pettiest giver there ever was.

A win

Not sure why this was classified as an office party fail by @ClareBearNC. It is such a win! What a glorious Christmas tree ornament to receive. Of course, we understand it’s an acquired taste, and not everyone can appreciate it.

Tweet courtesy of Twitter/@ClarebearNC

We think the glitter elevates what would otherwise be a really crappy gift. If Clare doesn’t want glittery reindeer poo on her tree, she should send that ornament over to us. We’d give it a prime spot on our tree this Christmas.


You know what kind of drunk you are. You know what kind of drunk your best friends are. You know what kind of drunk your siblings are. What you probably don’t want to know is what kind of drunk your boss is.

Tweet courtesy of Twitter/@darksidedeb; Photo by Scott Webb on Unsplash

This Twitter user got a firsthand experience at just the kind of drunk her boss is. Can you guess which? Yeah, he seems a little bit desperate and delusional. We wonder how she got away from that situation, or if she made a game of it.

Baby face

Some people have baby faces and look perpetually young. That can be a problem because people might just assume they are younger and treat them poorly as they grow older. They might be treated as a child for longer than anyone would want.

Tweet courtesy of Twitter/@kbjwrites; Photo by Naassom Azevedo on Unsplash

Poor @kbjwrites here does have a relatively young-looking face. It makes sense that she would be mistaken for someone’s child. But if this is a work party, shouldn’t people know who she is? Why are people still questioning her age?


It’s nice to be in a workplace where everyone is friends, or at least friendly. Sometimes the work/life boundaries can get pretty blurry, but at least you’re working with people you like. This next workplace seems like that kind of place.

Tweet courtesy of Twitter/@timdrake; Photo by Milan Popovic on Unsplash

It’s sweet that the boss was excited for everyone to meet his new girlfriend. But things turned south real quick for @timdrake. Are you guys asking the same question we are? Did the ex and the boss hit it off the previous year?

No use being sober

You might feel like you have to protect your reputation at an office party. Considering the amount of alcohol usually involved, you might even want to hold back a little, so you don’t get drunk and do anything silly. But sometimes that just doesn’t work.

Tweet courtesy of Twitter/@MissChliez; Photo by Klara Kuilkova on Unsplash

Being sober isn’t a guarantee that you won’t embarrass yourself! @MissChliez’s experience is proof. She didn’t drink at all at the party and still made a mess of herself. Maybe next time, she should consider wearing flats or sneakers instead of heels.


This next office party fail will teach bosses not to keep their expensive alcohol in their office. Unless, of course, they want their employee to come in and grab whatever bottle they please for the office party. Plus, it might have been a gift that they hadn’t taken home yet.

Tweet courtesy of Twitter/@CrohnsNinja

It’s safe to say that this coworker who opened up the $10k wine is now an ex-coworker. While it wasn’t technically his fault—how was he supposed to know how much the bottle cost?—it is still really upsetting for the boss to lose that much money.

Uh oh

It’s always lovely when office parties allow plus ones. It can make you feel less anxious having someone from your home life there beside you. Plus, it’s a great way to meet other people! Just make sure your plus one doesn’t do anything to embarrass you.

Tweet courtesy of Twitter/@kittykaresless

Uh oh. Not a good idea to bring your boyfriend who has no filter in social situations like this. That remark will most certainly reach the boss’s ears, and someone is getting reprimanded the following day for sure, or at least teased.


First of all, why does a party prop in the shape of a gun even exist? There are other ways to package exploding party streamers. Second of all, this gun should have come with a warning! They’re lucky it was the ceiling and not someone’s face.

Tweet courtesy of Twitter/@rae1273

This is a fail because, besides paying for the party, the boss also has to pay for the damage done to the ceiling. Next time, get party poppers like ordinary people. Why would anyone think a gun-shaped anything is a good idea?

Can’t get rid of me!

Getting intoxicated is almost always encouraged at parties, but the host has every right to kick you out when you get destructive. Of course, people are kicked out in the hopes that they won’t come back. But this lady was determined.

Tweet courtesy of Twitter/@Barnees5; Photo by Mark Kleen on Unsplash

You can take the lady out of the party, but you can’t take the party out of the lady! If she’s not done turning up, then she will be there until the doors close. She probably stumbled back into the party like, “You can’t get rid of me!”

He’s technically right

Here’s another drunken tale from an office party. Yet another reminder that when bringing a plus one, make sure they’re someone who can hold their drink. Otherwise, they might go around accusing people of murder.

Tweet courtesy of Twitter/@dierdre_ring; Photo by Markus Spiske on Unsplash

Technically, @deirdre_ring’s husband isn’t wrong. However, the coworker was not the one who committed said murder. And we imagine your wife’s office party is not the place to get political or start randomly yelling at people. This must have haunted Deirdre for a while.

The fortune teller

Well, this is the best #OfficePartyFail by far! You have to love it when bosses and coworkers have fun together. This is possibly the most hilarious kind of shenanigan any employee can ever pull on their boss. And we are delighted the boss let her!

Tweet courtesy of Twitter/@EmpressOfThePit

Suddenly there’s a line snaking out of the boss’s office. Intoxicated people were waiting to get their tarot cards and fortunes read, their futures beholden unto them on the reflective sheen on their boss’s bald head. That must have been one heck of a party.

To a T

We all have that one coworker who follows every instruction the boss gives down to a T. They’re usually the ones who take everything literally. These kinds of people are good to have in the workplace. But sometimes, they’re too detailed for their own good.

Tweet courtesy of Twitter/@thaliaevans

Whoever took the order at the cake shop is one of those people for sure. Did it not occur to them that “Happy retirement Peter and use a nice font” sounded just a little bit weird? Doesn’t matter, because the man of the hour found it funny too.

Cruise gone south

We would like Twitter user @MissAlissaNoel to disclose what company she works for because anywhere that holds an office Christmas party on a cruise ship sounds like a stellar place to work. Although maybe they shouldn’t have done this in Seattle.

Tweet courtesy of Twitter/@MissAlissaNoel; Photo by Tim Marshall on Unsplash

If this party had been a mid-year summer office party, there would have been a better chance at the event going swimmingly. Imagine going on a cruise in the summer, getting your tan on, and being around work people but not having to work!

Karma comes quick

This is why when you go out in social situations as a couple, you should have each other’s backs. Otherwise, karma comes and gets you quick. We’ll let this Twitter user tell you how he learned that the hard way.

Tweet courtesy of Twitter/@Gogogadgetmark; Photo by FOODISM360 on Unsplash

So now both Mark and his girlfriend have food prints on their butts. Maybe it’s time to call it a night and just go home? It’s a little mortifying to have stains on your behind for the entirety of an office party!

The hard way

Sometimes you have to learn things the hard way. Like failing a math test teaches you that you shouldn’t pull all-nighters at the last minute. Or like winning the Ugliest Sweater Award teaches you that your Christmas sweater is ugly.

Tweet courtesy of Twitter/@lilliluwho; Photo by Tandem X Visuals on Unsplash

Yup, we would say this is a fail. Maybe not an office party fail, but a life fail/fashion fail in general for @lilliluwho. She was out here wearing that sweater thinking she’s Anna Wintour at the Met Gala when really, it just didn’t cut it.


This must be the most BAMF-turned-pathetic way to quit your job. Not leaving with your head held high, but literally on your butt. The energy is way too chaotic; we can’t tell if this was a tragedy or a laughing matter.

Tweet courtesy of Twitter/@ughhitsashley; Photo courtesy of Julien L on Unsplash

Lesson learned: don’t quit your job when you’re drunk and stumbling out the door. Let an office party be precisely what it is—a party at the office. Leave work at the door and don’t think about how much you hate working there until you’re sober.

Failed flirtations

Sometimes you want to make your move on a cute guy, but you just don’t have the courage to. What better time to do that than at an office party when you’ve had a few drinks in you? Alcohol is the ultimate liquid courage, after all.

Tweet courtesy of Twitter/@LisaWerkmeister

Unfortunately, there’s a line between being just bold enough and crossing over to the deep end of being a clumsy drunk. While this may seem like the worst-case scenario, we would like to argue if Lisa really choked on the cherry stem would be worse.

A tragedy

While we have read about some catastrophic office party fails in this thread, we have yet to come to the most tragic one. That is, until now. There is nothing sadder than knowing there’s a party going on but not getting invited.

Tweet courtesy of Twitter/@bigsoccerboi; Photo by Nik Shuliahin on Unsplash

Poor @bigsoccerboi. All he wanted was to be included and be seen as a fellow employee. Whoever was in charge of that office party should be ashamed of themselves! An office party should consist of everyone who works there no matter their rank.

Bad timing

We’re reading this tweet, and all we are thinking is, who holds a party on a Monday night? Why would the boss sign off on this when he knows he still needs people to come into work on a Tuesday?

Tweet courtesy of Twitter/@Billy_Pentz

The boss shouldn’t be surprised that no one showed up the next day. This is precisely why parties should be held on Friday! Everyone can get as smashed as they please without having to worry about waking up early for work the next day.

Not ugly

Ouch. This offense is right up there with regifting someone’s present for you. Twitter user @heddak wore a sweater that she got gifted to an ugly Christmas sweater party. But it wasn’t meant to be an ugly sweater! It was just a nice gift, or os her coworker thought.

Tweet courtesy of Twitter/@heddak

Heather probably should have thought twice before wearing a said sweater to the Christmas party. It must have been awkward when the coworker who gave her the sweater saw her in it. “So you think the sweater is ugly, huh?” Not very nice, Heather!

Ho ho hooo

We love that fashion these days incorporates technology. No, we’re not talking about things like Google Glass and the Apple Watch. We’re talking about those Christmas sweaters that light up and sing Christmas songs; the kind @molloyd23 was wearing one year.

Tweet courtesy of Twitter/@molloyd23; Photo by Fabio Porta on Unsplash

Oh, to be at a Christmas party wearing a malfunctioning vest. There’s no way to fix the vest unless you want to sneak out to undo all the wiring inside it. That’s effort. All you can do is just take the vest off, but where’s the Christmas spirit in that?

The show must go on

Isn’t it so much nicer to work in an environment where the boss knows when to let loose and have some fun at the microphone? Some of us aren’t as lucky as @mseric, who attended a karaoke office party one year.

Tweet courtesy of Twitter/@mseric; Photo by Anna Earl on Unsplash

You know what they say in the business. The show must go on! Even if you take a tumble, keep the performance going even if you can’t get back up. This boss put on a stellar performance and a masterclass in show business!

To be single

Don’t you just love it when your boss calls out your singleness in front of all your coworkers? It’s like, “Yeah, I know I’m single, but you don’t have to shout it from the rooftops!” This Twitter user might have won a prize, but the remark was a big L.

Tweet courtesy of Twitter/@mommybird97

Can we also just take a second? Because it says, she won a free stay for two at a hotel. Nowhere does it say that it’s for a couple. She could go with her best friend; she could go with a cousin – it shouldn’t matter!

A win, part 2

This is yet another situation that we consider a win but was classified as a fail. Whoever shows up to a party injured but doesn’t let that stop them from having the time of their lives should be greatly awarded.

Tweet courtesy of Twitter/@lagunatic92651; Photo by Tom Claes on Unsplash

Sure, dancing with your arms can be more fun. But nobody said that you couldn’t dance without them! The only important thing is that you still enjoy yourself at the party. Doesn’t matter if it’s your arm in a cast.

Food shortage

When the committee in charge of catering severely messes up, the party is doomed to go south. Food is the one crucial element of a party. No food and the guests will get cranky, which we suppose happened at this office party.

Tweet courtesy of Twitter/@TourMegaWorld

How the party planning committee managed to miss 60 people at the office entirely is beyond us. Unless, of course, people brought plus ones to a party that didn’t plan for plus-ones. Either way, this must have been a pretty disappointing party to attend.

Firing people over Christmas

When you come to an office Christmas party, you’re expecting to enjoy the company of your coworkers and some eggnog. You are not expecting to get fired. So how does the boss soften the blow for the people whose contracts he needs to terminate?

Tweet courtesy of Twitter/@therealmtran; Photo by Tim Mossholder on Unsplash

We understand that this may be the boss’s way of making the news a little easier to take. But it ends up playing like one big, sick joke. Just because it’s Santa Claus handing you a termination letter doesn’t mean you’ll consider it a present.

Petty boss

We’ve all had that one boss who takes out his disappointments and frustrations on his employees. They’re always more than just a little bit petty. But we have never heard of someone pettier than @Billy_Pentz’s boss. We’ll let him tell the story.

Tweet courtesy of Twittre/@Billy_Pentz

It must have been an honest mistake that the owner’s name got left out of the raffle. He shouldn’t have taken it own on the employees. He indeed shouldn’t have delayed their Christmas bonuses until the summer. Ridiculous, we say!

Potluck gone bad

Potlucks are a great way to cut costs at parties. At least the company doesn’t have to pay for food, and people can still have fun and be creative with what dish they bring. The committee should specify that the people allowed to bring food should be able to cook.

How do you identify the culprit when everyone called in sick from food poisoning? It could have been any of the dishes that caused it. Maybe it was Sally’s eggnog? But it could also have been Greg’s potato salad or Freddie’s roast beef.

Wrong party

Has anyone ever showed up to the wrong party? Maybe you misheard the address when it was given to you, or you put the incorrect address into your car’s GPS. If this has ever happened to you, it’s a party fail from the start.

Tweet courtesy of Twitter/@NickyCage03

Poor grandma. We hope she quickly found the destination for the correct party. At least she immediately realized that there wasn’t anybody she knew at that first party. It must have been awkward to walk into a room full of people who are staring back at you, wondering who you are.


Nobody knows how to humiliate you more than your friends. And if you have those kinds of friends at the office, you know you’ve chosen the right place to work. Only the best of friends will have the guts to embarrass you on purpose.

Tweet courtesy of Twitter/@darindg1961

Poor @darindg1961 has to suck it up and deal with it. Now everyone at work has seen this picture of him, and that’s okay! He just needs to get drunk enough to forget about it for the duration of the party.