The 100 Most Embarrassing Photos Ever to Find Their Way Onto the Internet

A long time ago, in an offline galaxy far, far away, you could shrug off embarrassing moments and pretend they didn’t happen. Nowadays, however, such moments are immortalized on the web – which may be bad news for the following boneheads but is very much a good and hilarious thing for the rest of us.

This chest-bump fail, for example, made two volleyball players look a little more intimate with each other than they’d probably hoped to appear – well, in public, anyway.

Thenks for the reminder, dude. We always forget Mather’s Day.

Nothing says sexy quite like sticky bug tape.

ADVERTISEMENT

Minutes before departure, when you’re sat next to an open seat looking smug, always remember that a big guy in his underwear is on his way to ruin your day.

Heads turned when Joel squelched his way toward the finish line. Just grin and bear it, Joel, grin and bear it.

ADVERTISEMENT

“Hey Cindy, do you remember that time we got totally wasted and you took a dump in your parents’ sink? No? Well, that’s what Facebook’s for.”

ADVERTISEMENT

Never ask this guy for directions. You’ll regret it instantly.

ADVERTISEMENT

Dude, you’ve got to be kidding me. The water’s not that cold.

ADVERTISEMENT

Sure, Grandpa can be an ass sometimes, but this is really rock bottom.

ADVERTISEMENT

Ever get that not-so-fresh feeling?

ADVERTISEMENT

How embarrassing. Running shoes on the beach? Whatever next?

ADVERTISEMENT

And just like that, little Jimmy never went out in the sun ever again.

ADVERTISEMENT

“Maintain eye contact and play it cool. Maintain eye contact and play it cool…”

ADVERTISEMENT

Just a second. I’ll be right with you…

ADVERTISEMENT

What a parking spot. And so polite as well. No, thank you.

ADVERTISEMENT

The girls had really let themselves go by the time shooting started on the third Sex and the City movie.

ADVERTISEMENT

This vacation snap must have seemed fun at the time. Now? Not so much.

ADVERTISEMENT

Dude, she was so into me. I think I’m in love.

ADVERTISEMENT

Can you, er, just keep looking at the water for a few more minutes? Trust me, just keep looking.

ADVERTISEMENT

Status update like no one’s watching…

ADVERTISEMENT

Suddenly the Johnson family slideshow became the laughing stock of the entire neighborhood. “Quick, Gerald, turn it off! For God’s sake, turn it off!”

ADVERTISEMENT

There’s no “i” in “team,” but there are two in “spirit.” D’oh!

ADVERTISEMENT

Some people were just born to be hair donors.

ADVERTISEMENT

“Quick, pick your teeth up and keep walking. No one saw you. Keep walking.” Tina repeated this mantra to herself and quietly slipped away.

ADVERTISEMENT

Marvin Gaye’s family had no problems with Robin Thicke’s latest single, “Tan Lines.”

ADVERTISEMENT

Tom Cruise never has his photo taken without his trusty footstool.

ADVERTISEMENT

When you’re busted trying to act cool with geotags.

ADVERTISEMENT

Holy crap, someone slapped this kid so hard that he’s bleeding. This wound makes our eyes well up just looking at it.

ADVERTISEMENT

When your awkward tan lines reveal the secrets you’d rather not share on Facebook.

ADVERTISEMENT

Street proctology is never going to be as popular as street theater.

ADVERTISEMENT

Surely the big guy did this solely to attract the attention of his two hot helpers here.

ADVERTISEMENT

Back sweat. It’s obviously back sweat, right?

ADVERTISEMENT

The funny thing is that it looks like the two fresh-looking dudes in the middle didn’t even know their bleary-eyed photobomber.

ADVERTISEMENT

We’ve seen slices of bacon that were less streaky.

ADVERTISEMENT

It’s best to remove any background mirrors when attempting to create fake photo fails.

ADVERTISEMENT

“Yep, I’m listening. Geology. Rocks. Nature. This is just the best spot ever.”

ADVERTISEMENT

This cringey nightclub gem set a new record for the fastest untag in Facebook history.

ADVERTISEMENT

Always, always check new clothes for labels before heading out – especially if you got them on sale.

ADVERTISEMENT

She’s obviously a Parliament Rolls of Medieval England enthusiast. Daddy must be so proud.

ADVERTISEMENT

That awkward moment where you inhale someone else’s beach ball.

ADVERTISEMENT

When sleeping with your mouth closed suddenly becomes the most important thing in the world.

ADVERTISEMENT

Here’s someone who took the phrase “keep your eye on the Frisbee” far too literally.

ADVERTISEMENT

This guy just got a rock-hard and shaved-smooth dose of reality. He’s crying on the inside.

ADVERTISEMENT

Don’t worry, kid. Somebody else already took a picture of those embarrassing tan lines.

ADVERTISEMENT

“What’s for dinner? Because I just ate dirt for lunch.”

ADVERTISEMENT

The shocked faces of those under and around this lovely lady are really something to behold.

ADVERTISEMENT

Check out this snap of party-going teens. The music stopped. The lights came on. But Anna noticed too late. Tragic.

ADVERTISEMENT

High wasted pants, sandals and a sweater vest? How embarrassing.

ADVERTISEMENT

“You put your right leg in; your right leg out; in, out, in, out – oh, jeez, stop shaking it all about.”

ADVERTISEMENT

Bad T-shirt choice, dude. Bad T-shirt choice.

ADVERTISEMENT

This might just be the most effective safe sex ad we’ve ever seen.

ADVERTISEMENT

If you’re going to get drunk and show off how flexible you are, make sure you’ve washed your feet first.

ADVERTISEMENT

From sexy to awkward in one, two, pee.

ADVERTISEMENT

Perhaps Big Fat Baby wasn’t the best costume choice.

ADVERTISEMENT

What? Mimes like to take limo rides too.

ADVERTISEMENT

When they said high-waisted jeans were cool, this is not what they had in mind.

ADVERTISEMENT

Proof if ever it were needed that sexy selfies should never be attempted in the office.

ADVERTISEMENT

To be fair, this T-shirt choice was always going to end badly.

ADVERTISEMENT

Note to self: always crop out the Beardify watermark before committing your fake beard selfie to Twitter.

ADVERTISEMENT

Next time pack a change of clothes.

ADVERTISEMENT

We’re guessing that this guy’s gonna wake up thirsty and dehydrated.

ADVERTISEMENT

The barman probably should have cut Peter Griffin off two and a half beers ago.

ADVERTISEMENT

And just like that, this blonde’s hot-and-sophisticated spell was broken forever.

ADVERTISEMENT

This nose pick is even more hilarious because it was caught on Jumbotron.

ADVERTISEMENT

This is what happens when the Kiss Cam operator gets dumped the night before.

ADVERTISEMENT

Ah, a moment for these two lovers to cherish forever is wonderfully captured on Kiss Cam.

ADVERTISEMENT

Now, young sailors, did this dweeb wedgie himself on the port or the starboard side of the yacht?

ADVERTISEMENT

Remember, kids, always check your Facebook profile selfies for incriminating sex toys before uploading.

ADVERTISEMENT

“Honestly, this never usually happens to me…”

ADVERTISEMENT

She’ll never need to be told to only tackle the players’ legs again.

ADVERTISEMENT

Well, she was looking a bit hot in all that sunshine.

ADVERTISEMENT

Now that’s using your head – and neck. Ouch.

ADVERTISEMENT

“That’s right, stand around laughing. Don’t lend a hand or anything!”

ADVERTISEMENT

Remember that time when Brad May kissed another ice hockey player? Nope? Neither does he.

ADVERTISEMENT

Insert inappropriate joke about airbags.

ADVERTISEMENT

And you think your dad is embarrassing.

ADVERTISEMENT

What could he have possibly seen back there?

ADVERTISEMENT

“Please tell me that’s an iPhone in your pocket!”

ADVERTISEMENT

“Mr. Montgomery, can you tell our viewers how you got stuck in the ground?”
“Come closer and I’ll show you.”

ADVERTISEMENT

If you’re going to leapfrog, probably best to check that you’re wearing underwear first.

ADVERTISEMENT

“Hang in there, buddy, I’ll just grab my phone – the camera’s awesome on it.”

ADVERTISEMENT

Sometimes headlines just write themselves…

ADVERTISEMENT

Nope, you won’t find your dignity up there, either.

ADVERTISEMENT

“Er… Sarge, you okay?”
“Yeah, Kowalski, just takin’ a load off.”

ADVERTISEMENT

A scene that didn’t make it into The Human Centipede for being just too terrifying.

ADVERTISEMENT

This is exactly why you shouldn’t sit on the fence. You might end up looking a bit silly.

ADVERTISEMENT

“Bro, why don’t I remember last night?”

ADVERTISEMENT

“Oh heck, this is gawna hurt, yah see.”

ADVERTISEMENT

Janine couldn’t understand why her Snapchat conversation suddenly went quiet.

ADVERTISEMENT

Because nothing says sexy like a mouthful of raw fish.

ADVERTISEMENT

Ah, Valentine’s Day, that magical time when even toilet brushes become signs of romance.

ADVERTISEMENT

We shouldn’t be laughing really, should we?

ADVERTISEMENT

Sometimes, to win at wrestling you need to get your hands dirty.

ADVERTISEMENT

Perhaps bring-your-kids-to-work day isn’t for everyone.

ADVERTISEMENT

This skier lets it all hang out on the slopes.

ADVERTISEMENT

The Slip ’N Slide: bringing people together since 1961.

ADVERTISEMENT

The classic Dukes of Hazzard hood slide. How cool is this guy?

ADVERTISEMENT

Thanks to the internet, this baby will have to live with the shame forever – and you can tell by its eyes that it knows. Isn’t technology great?

ADVERTISEMENT

Badass 2015 Justin Bieber wishes photos like these would disappear, like, forever.

ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT