40+ of the Most Embarrassing Office Party Fails Ever

Any office worker could tell you about their love/hate relationship with office parties. They can be uncomfortable, but they make for some good memories, whether funny or awkward. From unknowingly flirting with the boss’s wife to making out with a co-worker only for the whole office to see, we’ve compiled a list of the most embarrassing office party fails ever!

So He’s the Jerk

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.

So He’s the Jerk

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!

A Friendly Slap

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.

A Friendly Slap

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.

Tan in a Can

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.

Tan in a Can

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.

That’s the Boss’s Wife

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.

That’s the Boss’s Wife

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!

Ugly Xmas Sweater Party

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.

Ugly Xmas Sweater Party

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?

Ate One by Herself

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.

Ate One by Herself

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.

Fell Into the Punch Bowl

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.

Fell Into the Punch Bowl

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.

Boss’s New Girlfriend

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.

Boss’s New Girlfriend

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.

10 Tasty Cucumbers

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.

10 Tasty Cucumbers

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.

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