Awkward Pictures

Everyone had their cringy and awkward moments but these photos capture the perfect time of an uncomfortable moment. Awful facebook posts and conversations, weird T-Shirts and a lot of other cringy things are what you can find on this list. Some of them will make you laugh and others will make you want to cry and you’ll regret seeing it. Please learn from these people’s mistakes so we don’t see more cringy stuff on social media and even in real life. Here you have 50 pictures of the most awkward moments in history, go ahead and read at your own risk.

Wrong place and shirt

This guy was at the wrong place at the wrong time with the wrong shirt. If he is all about being white, he should be bragging about it next to this woman.

This bar lean

We don’t understand this man’s legs. What is he even doing? Is he sitting, is he standing up, that stool isn’t tall enough for him, is that his way of hitting on with that girl? We don’t know.

Halloween walk of shame

Well, that’s awkward. That guy must have had a strange Halloween and he finished it on the train dressed as a fairy. He even wore a tiara! Maybe he is ok with that but it was awkward for sure.

This moment

It can’t get any more awkward than that. But this can end in a cheesy love story or a creepy one, depending on what happened next. You’ll have to see the next pic to find out.


Yes, this is the most awkward thing we’ve ever seen. The guy found the girl on twitter and answer her tweet and said he wasn’t taking a picture of her! It’s sad.

Photo stealer

Stealing pictures from the internet and pretending to be yours is awful but saying that you ARE the guy in the picture and then getting caught must be so awkward. Not cool.

When your shirt is supposed to say Canada

Sometimes a placement of the words in a t-shirt will ruin your pic. This one is especially awkward, we know that this girl loves Canada but she may love another thing too.

This conversation.

Oh no, a cultural appropriation fight. We never thought we would see this two guys face to face and we know is totally awkward but maybe they just talked it through… or not.

A very uncomfortable interaction.

We have no idea what was going on but that man must be smiling because he wants to get home alive. Or maybe he is in love with a half bird half man and he is not afraid to show it.

This actually happened out in our world.

This guy just got together to hang out with their girlfriends… some anime pillows. That one on the right is even kissing the pillow! It’s both awkward and pathetic honestly.

This pregnancy announcement.

Why would you choose this way to announce that you are pregnant? The face of the father and daughter don’t show happiness at all. Maybe it was meant to be funny but is very awkward.

This situation.

Imagine having to pee or poop in that toilet where everybody can see you, you will feel like you’re in jail or something. Nothing can be more awkward than this.

this one might actually be worse.

The designer or engineer behind this has an evil mind. It’s impossible for two men to fit there and pee without having an awkward moment. That’s not good at all.

This couple shot.

This couple is extra creepy, everything about this shot is awkward: the man being extremely taller than her, their faces, their clothes. It hurts to look at this photo honestly.

This party.

This guy outfit is everything but what is he doing at this party? Everything here looks wrong, this party is super weird and awkward. It looks like the comic con met a high school prom.

This father.

Look at the father’s face here, it’s just hilarious. Imagine how uncomfortable that situation was for him, he’s not enjoying that situation at all. The girls seem happy with their new underwear, tho.

This discovery.

Oh no, this two guys had the exact same idea for their outfits and both took the exact same train and got caught in this awkward situation. Is like going to a Halloween party and somebody has your same costume.


Ok, it happened again. Coincidence? I Think not. It was the awkwardness monster cursing everybody and making them use the same outfit the same day at the same place.

This unfortunate coincidence.

So this guy looks almost the same as the guy featured on that crime stoppers add. It’s that awkward moment when you know your friend is thinking that you are a criminal.

This engagement Photo Shoot.

We are so happy this couple is getting married but was this photoshoot necessary? Why would they do that? It looks very awkward and we are sure that it also was awkward for the photographer.

And this one.

Ok, we see that engagement photos can be VERY awkward. Everything here is awkward, that dude’s face, their positions, and the leaves. What leaves got to do with marriage? We don’t know.

His face.

This guy is leaving the dream of some, he is surrounded by cheerleaders but his face reflects his true emotion: awkwardness. He seems like he doesn’t want to be there at all.

This beard related fail.

If you want to fake a beard on your profile pic remember to erase the app logo. This guy had a super awkward moment on twitter when someone discovered that it wasn’t his real beard!

This hover-hand.

This hug looks super awkward. Maybe these girls just didn’t want to be touched by that guy or it was his choice but it makes everything worse. Also, that woman’s face in the back is hilarious.

And this double hover-hand.

Not again! Pro tip: If you are hugging two girls and taking a picture of it, don’t do this. It looks awful and awkward and will make you look very bad. Even if you look like a Sprouse brother like this dude.

This post.

Oh no. That comment on the Facebook post will make everything uncomfortable between this guy and this girl. She doesn’t need to give any explanation about her removing her tag so making a comment with her name is super mean.

This question to the mayor of Hiroshima.

The picture says it all. That awkward question and answer to the mayor of Hiroshima just after the world war are not good. Maybe the next time the interviewer will do a little research.

Avril Lavigne.

Why would you throw a meet and greet if you don’t want to get pictures with your fans? Usually, the stars hug their fans for the pic, but this one of Avril Lavigne looks awkward.

This cover-photo cropping.

When you see this facebook cover for the first time your mind will take you to a dirty place but don’t worry, it’s just two people holding hands. This guy will have to change the pic or at least the cropping.

This awkward assumption.

Ok, that’s awkward. We understand this girl or guy who commented without knowing what was happening with the dog but that response just goes into our hearts. Ouch, it hurts.

This special ingredient that was given a miss.

What is going on in this restaurant? That California Roll may be a little weird and the ticket super awkward for the one who just ate the whole thing. Thankfully it was removed!

This design.

This design is super weird and awkward. Glitter is not a color, that bag doesn’t even have a lot of it and we are sure that it costs more than your car. Pretentious designers are just the worst.

This suspicious water bottle.

The placement of this straw in the water bottle is awkward and we never want to imagine the great Buzz Lightyear like this. A kid sipping this would look very creepy and we don’t want that.

And this surprise in a water bottle.

Cold water is awesome if you are thirsty but when the ice is shaped this way it’s super awkward. How in the hell happened? The awkward force is strong with this one.

These direct instructions.

We have no clue of what this musician actually have to do here but those instructions look very clear. Imagine reading that out loud and feeling the awkwardness in the entire room.

This perfect alignment.

This is a funny one. The placement of the ad and the article is perfect for a great joke. Poor woman, her friends will laugh at her for the rest of her life because of this magazine.

The missing letters on this shirt.

Not again. We think that Canada should think before putting its name on a shirt or sweater because there can be a hidden message in its letters. Or maybe is an actual message from this girl to her tinder matches.

This breakup approach.

Oh my god, this girl is ruthless. He broke up with four guys at the same time because she made up with her ex. The most awkward thing is that she created a group chat to do it!

This cringey mistake.

That’s savage, messing up a baby ultrasound with a lasagna is bad. That awkward comment telling the guy that it’s actually their daughter really made us cringe a lot. Ouch!

This apparent face-swap.

This twitter conversation is super awkward. Snapchat face swap filter has been everywhere lately but this photo is real and the Capitals account thought it was a face swap. Poor girl and her dad.

This job description.

Oh, the irony. This organization fights for human rights and against slavery but doesn’t pay their own interns. That’s basically slavery and we can’t help to see the contradiction there.

This ad.

What is that? We have no clue but we all know what it looks like. The advertising industry needs to think before putting things like this in a magazine. People’s minds may go places…

This unfortunate coincidence.

…or maybe they don’t fit. We love these coincidences and the timing of this truck hitting a bridge is perfect. We don’t know what it’s carrying but they should change their slogan.

This cat’s resurrection.

Oh no, this woman buried out a cat thinking it was her and it wasn’t. She even made a facebook post about it but then had to say that it was alive. Most awkward thing ever.

This painful exchange.

This is so painful to read. Poor women and just everyone who had to read that facebook post. Next time you comment something, please read and think before you do it.

This free gift.

Oh, that again. The one in charge of that newspaper cover must have a dirty mind and he or she knew that everybody will place the papers that way. It’s awkward as hell, honestly.

This advice.

This pic got pretty viral on Twitter. We know that the designer of this sweater had a good intention there but the execution was not the best. “Don’t be happy, worry” is super cringy and sad.

This misinterpreted news.

We have a lot of examples on the list of people not reading or understanding a facebook post and just commenting something awkward. “Not so yay”, those words hurt like hell.

This complete misunderstanding.

This one is extra funny. Thinking that TRESemmé is a woman called Theresa May is hilarious. Poor the woman who had to suffer that embarrassing response but we are LOLing so hard.