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The Most Hilariously Awkward Real Life Moments

September 25, 2022

It doesn't matter how sleek we may think we are, no one is safe from running into a potentially embarrassing situation. But there are different levels of awkward. On one hand, there's "I run into my boss at the supermarket" awkward. And then there's "I matched with my best friend's current boyfriend on Tinder" kind of awkward. Yikes!

So whether you accidentally sent a NSFW photo to your work group chat or you tripped and dropped your burger at McDonalds, these cringy real-life moments make us feel a bit better about our own awkwardness.

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Torturous Music Is In The Works

Torturous Music is in the Works 1
Facebook

Peter Turik, the front man for a Toronto-based metal band called Witchrot, discovered that the woman he had been in a relationship for seven years had been sleeping with the band’s guitarist. Under the circumstances, Turik realized that the show could not go on, at least not for a while anyway. So, he explained why the band was going on hiatus and he didn’t hold back. But there’s always a silver lining like the fact that his girlfriend’s affair and his guitarist’s betrayal inspired him to write some serious torturous music. Yikes. Next time, hire a social media manager, man!



The Corpse In The Garbage Bag

The Corpse in the Garbage Bag 2
Reddit/MahatmaBlondhi

Decorating for Halloween is crazy exciting. Unfortunately, putting everything away isn’t as much fun, which is why you might still find an old set of Christmas lights under the living room table, or even a few Jack O' Lanterns hiding in the closet. But this homeowner got a major incentive to clean up after a fake corpse Halloween decoration he left on the porch attracted the attention of authorities. Bet he’ll never take this thing out for Halloween ever again!



Are You Lying To Me?

Are You Lying to Me? 3
Pinterest

This woman’s self-esteem came crashing to the ground after she posted a poll on social media asking whether people thought she was pretty or if they were just lying to her about her looks. Well, only 20% thought she was genuinely pretty and the other 80% claimed they were lying to her about her good looks. But she can take comfort in knowing that only 150 people voted out of 7.9 billion humans on the planet. That being said, don't ask questions you don't want to know the answers to.



Son? Were You Shot?

Son? Were You Shot? 4
Pinterest

If there’s one thing this son will never be able to accuse his mother of is not being worried about him because she was. When she read that someone in his neighborhood had been shot dead, she immediately panicked. Oddly enough, instead of calling him, she grabbed a pack of cigarettes and started smoking like crazy while she texted and waited to see if he was okay which is all levels of cringe. In her emotional outburst, his own mom forgot how old her son was.



Showing His Family His Pokémon Collection

Showing His Family His Pokémon Collection 5
Reddit

This poor guy! He was so impressed with his Pokémon collection on his Nintendo Switch that he decided to share his enthusiasm with his family over Thanksgiving. But judging from the look on everyone else’s faces, it’s a safe bet that they weren’t particularly proud of him. Can you imagine the pearl-clutching grandparents' reaction if he tells them he threw away all his money on Dogecoin?



You Texted My Dead Husband

You Texted My Dead Husband 6
Pinterest

No one ever gets over the loss of a loved one, especially when that loved one is a spouse. But there are moments in the grieving process where you might try to forget that the person’s gone forever. Sooner or later, something will pop up and remind you of what you've lost. In this case, that reminder came in the form of a text from her dead husband’s number neighbor who had no idea that he had passed away. Can you spell awkward?



Rest In Peace, Uno

Rest in Peace, Uno 7
Pinterest

When this guy posted a photo of a wooden box with the word Uno on it, one of his friends assumed that he was referring to the highly addictive card game of the same name. Unfortunately, he quickly learned that this guy had a dog named Uno who had passed away. You won't find those fun multi-colored playing cards, but the poor dog's ashes. We're. Just. Speechless.



Desperately Selling Fidget Spinners

Desperately Selling Fidget Spinners 8
Facebook

You've seen it before! That old toy you used to play with in the '80s becomes hot and trendy again and they're suddenly worth thousands. Well, back when fidget spinners were all the rage, this person decided to buy about 6,000 of them hoping they would become a rare commodity worth millions in the future. Unfortunately, his plan failed and now he’s desperately looking for a way to dig himself out of the financial hole he’s in. A good rule of thumb is to never invest anything you're not willing to lose.



Gary Has 0 Friends

Gary Has 0 Friends 9
Pinterest

Poor Gary! Social media can be such a cruel world. As if getting no birthday wishes wasn’t already bad enough, social media had to rub some salt on his wound and let him know that 0 friends cared about his birthday. But that’s okay, because sometimes it’s better to celebrate alone with your pets and family than to be surrounded by fake online friends.



Someone Please Fake A Birthday Party

Someone Please Fake a Birthday Party 10
Twitter/Texts with Threatening Auras

This woman wanted to get out of a date so badly that she came up with an elaborate plan and shared it on her private Snapchat. Unfortunately, she had no idea that her date’s friend was following her and ratted her out. She must have had a really awkward conversation with her date after this came to light and it’s a safe bet that they didn’t live happily ever after... at least not with each other.



Sorry, But You’re Not My Type

Sorry, But You’re Not My Type 11
Imgur/MeatyDogFruit

OUCH. This woman took a selfie only to realize there was a cute guy right behind her. When she realized how attractive the guy was, she took a few more photos, posted them on social media, and asked if anyone knew who the stud was. Well, the mystery man eventually got word that someone was crushing on him. Unfortunately, his response wasn’t what she had been expecting. And so, this love story ended before it even began.



He Lost His Job Doing ASMR Videos

He Lost His Job Doing ASMR Videos 12
Youtube

This dude was making ASMR videos at work and eventually, it came to bite him in the rear. Now, if you've been living under a rock, you might not be familiar with ASMR (autonomous sensory meridian response) videos. ASMR is a relaxing sensation that starts on the scalp and moves down the body. Well, this guy posted a video claiming he was doing ASMR while working and almost got caught. A few days later, he posted a video explaining that he actually did get caught and sadly for him, it didn't even go viral. Bummer.



No One Cared That He Was Leaving

No One Cared that He Was Leaving 13
Pinterest

This guy overestimated his importance in the lives of his co-workers, but he quickly learned that he wasn’t as valuable to the team as he thought when he pulled an April Fool’s joke that totally backfired. His coworkers fell for the joke, which let's face it, it wasn't much of a joke, and barely reacted to him leaving the company. Maybe this is a sign from the universe that you need to work somewhere where you're appreciated, man!



It Was The Worst Meal Ever

It Was the Worst Meal Ever 14
Pinterest

This may be the best boyfriend ever because he actually did his best to cook a decent dinner for his girlfriend. He even thought he had done a good job until a text popped up on her phone from her mom that revealed how she really felt about it. Everything would have been fine if he hadn’t been watching videos on her phone when the all-too-revealing text appeared. Hopefully, his next girlfriend will appreciate his cooking.



The Loneliest Beer Pong Game Ever

The Loneliest Beer Pong Game Ever 15
Pinterest

Beer pong is a drinking game in which players throw a ping pong ball across a table with the hopes of it landing in a cup of beer on the other end. The game often consists of opposing teams of two or more players per side with about 10 cups set up in a triangle formation on both sides. But this person shouldn’t have bothered to set this game up because judging from the post, no one is coming.



Would You Like To Sell Your Baby?

Would You Like to Sell Your Baby? 16
Reddit/sadcringe

This may be one of the creepiest texts anyone could ever send a mother. It turns out that the anonymous texter had suffered a miscarriage. Whether that’s true or not is unknown, but just thinking about getting this text sends shivers down our spine. The texter even went on to reveal that they had been stalking them on Facebook for a bit and even gave the baby a nickname. For all that is good and holy, we're going to assume this text is a bad joke.



She Wanted His Skinny Arms

She Wanted His Skinny Arms 17
Pinterest

An anonymous woman on social media posted that all she really wanted in this life "is skinny arms." So, naturally, some random guy assumed she was talking about a guy with skinny arms and he fit the description. So, he took his shirt off, took a selfie and replied to her original comment. But he was undoubtedly disappointed when she told him that she wasn’t necessarily looking for skinny arms on a man but rather on herself.



The Polar Opposite Of A Tinder Like

The Polar Opposite of a Tinder Like 18
Pinterest

Generally, people swipe right when they like someone, but a super like is a feature that a Tinder user can only use once every few hours and it allows the other person to see who super liked them before matching. Unfortunately, Graham was brutally honest and explained to this woman that if there was a “polar opposite of a super like” then he would have pressed that after looking at her profile. Ouch! Her poor, poor ego!



The Wedding That Never Happened

The Wedding That Never Happened 19
Imgur/OhMyYoureSexxy

This guy had the next 20 years all planned out, and within that time, he had figured out that he was going to be married by 2018. In fact, he was so sure that he set up a reminder of his wedding on his calendar but totally forgot about it. Then he remembered why he had done this but realized that he was no closer to finding his happily ever after than he was when he saved the date on his calendar.



Her Gift Was On Sale At The Salvation Army

Her Gift Was on Sale at the Salvation Army 20
Pinterest

This person saw a decorative glass with a swirling glitter design on the bottom that looked awfully familiar. Then she realized why that was. It turns out that she was the one that had given the glass an artistic makeover and then gifted it to a friend. But whoever said that you can’t put a price tag on friendship was lying because that friend donated the glass to the Salvation Army who put a price tag on it of $1.89.



That’s Just My Dad

That’s Just My Dad 21
Reddit

This woman went to see a hockey game with a handsome man sitting next to her. But there was something eerie about the photo. At least, that’s what the NHL team, the Washington Capitals thought when she uploaded a photo of herself with the guy using the hashtag #CapsSocialNight. So, the Washington Capitals commented “Great faceswap” on the woman’s post. But it turns out that there was a perfectly logical explanation as to why these two looked alike.



Grubhub Driver Got Called Bruh

Grubhub Driver Got Called Bruh 22
Pinterest

Valerie, the Grubhub driver doesn’t like being called a “bruh” because she is a woman. Of course, there was no way that the guy who placed the order she delivered could have known that until it was too late. By the time he realized his mistake, there was nothing he could do to make things right with Valerie. But he’ll definitely think twice before calling anyone else “bruh” ever again... I guess.



Sorry, Right Number!

Sorry, Right Number! 23
Pinterest

Cole was heartbroken when he learned that Camryn, the woman he had met at a bar the night before, gave him the wrong number. At least, that’s what the person that texted him told him in 2019. But a year later, the person sent Cole another text related to a group project by mistake and she identified herself as Camryn. So, it turns out that the wrong number was actually the right number. Unfortunately, she was definitely not the right person for Cole.



So Sorry For Offending You

So Sorry for Offending You 24
Reddit/Bebopcanoo

Grant B had set up a reservation for two at a restaurant. Unfortunately, bad weather forced the restaurant to cancel the reservation. And when they notified him, he lashed out with a horrible insult. But he didn’t think anyone would be hurt by his words because he figured the cancellation message was nothing more than an automated message. Then he discovered he was actually chatting with a flesh and blood human on the other end.



Hold On, My Ex Just Called

Hold On, My Ex Just Called 25
Pinterest

This person was having a virtual movie night with a girl. Unfortunately, they had to hit pause on the movie because the other girl’s ex called them. They figured the conversation with the ex wouldn’t take too long, but 27 minutes passed and the girl never replied to their inquiry to see if everything was okay. But it’s a safe bet that movie night was cancelled indefinitely.



The Speed Dating Fail

The Speed Dating Fail 26
Reddit/VoidTorcher

Speed dating is a type of matchmaking process which encourages eligible bachelors and bachelorettes to meet a large number of potential partners in a short period of time. This was certainly what the event in this photo was supposed to be about, but unfortunately, no one showed up except for the poor sap that took the photo. Maybe they got the date and time mixed up.



Who Are You?

Who Are You? 27
Twitter/@ladygaga

Ninja, aka Richard Tyler Blevins, is an American Twitch streamer, YouTuber and professional gamer with millions of followers. So, naturally, when singing sensation Lady Gaga asked on Twitter “What’s fortnight,” referring to the online game Fortnite, Ninja was more than happy to jump in and offer to explain it to her over the phone. Unfortunately, her response stung like acid on skin.



Just Retire Already

Just Retire Already 28
Reddit/VoidTorcher

Ryback was a former WWE star, who had been let go. Unsure of what his next move should be, Ryback decided to ask social media for help in figuring things out. So, he set up a poll on Twitter asking if he should return to WWE, go to upstart promotions AEW or Impact or retire. Well, most people voted retire. So, initially Ryback assumed trolls had hit the retire button, but he posted the poll two more times and got the same results. Awkward!



Sorry For Your Loss, Wanna Date?

Sorry For Your Loss, Wanna Date? 29
Pinterest

A guy on social media commented on a woman’s social media post, which was a photo of herself with her father. And he called the guy lucky for having such a beautiful girlfriend. But it turns out that the lucky guy was the girl’s father who had passed away. And yet that didn’t stop the embarrassed guy from taking advantage of the situation and asking her out on a date.



The Knock Knock Joke

The Knock Knock Joke 30
Pinterest

Knock knock jokes are often seen as kid’s jokes but there are a few adults who still use them. In most cases, the joke begins with knock knock and leads to a funny or lame pun in the end. Well, this guy may have been trying to use it to hit on a girl who seemed to enjoy it or maybe she was just being polite by typing lol. But her boyfriend didn’t seem quite as amused.



 The Insecure Man

 The Insecure Man 31
Pinterest

This woman loves to play XBox, but not by herself. Luckily, she can play in co-op mode with other players online. There's only one major snag. Her boyfriend is extremely insecure and doesn't allow her to play with other guys. And this became a problem when she had to tell an online male friend that she couldn't play with him anymore because of her jealous boyfriend. Ironically, her XBox buddy lives across the country, so her man doesn't really have anything to worry about.



The Not Invited To My Party List

The Not-Invited-To-My-Party List 32
Pinterest

When this guy was asked by a girl in primary school how to spell his name, he immediately got excited. Those types of questions often indicated that someone might have a crush on him. He figured it was her. Then it turns out that she was making a list for her party, except it wasn't the kind of list he wanted to be on. In fact, it was the kind of list that would make any guy at any age feel utterly gutted.



No Second Date

No Second Date 33
Pinterest

Sometimes, people go on a first date and feel that they’ve hit it off. Unfortunately, that’s not always the case. It certainly wasn’t for this couple. Well, the guy seemed to have fun and was nice enough to reach out to his date. Sadly, all she did was nag about the fact that he was a Star Wars fan who couldn’t shut up about the franchise. But at least the guy apologized for talking too much. And when he asked about the possibility of a second date, her response was more venomous than a cobra bite.



He Made The Girl Cry

He Made the Girl Cry 34
Reddit

Being a teenager is tough, just ask this guy who posted on social media how a girl in class reacted when the teacher partnered her up with him on a project. Most teachers like to pair students up with people they don’t often socialize with so that they’ll open up and socialize with someone new. But after the way that girl reacted, it’s a safe bet that these two will be lucky to complete their school project without any drama.



The Cancer Free Controversy

The Cancer Free Controversy 35
Twitter

One person tweeted that they were cancer free, as in the disease they had fought so hard to get rid off was finally beaten. Unfortunately, one of their followers misunderstood the illness for the zodiac sign and was awfully confused as to how on Earth someone could change their birth sign. Luckily, they found enlightenment and apologized, but the thing about the internet is that it never lets people forget their slow moments.



The Epic Negotiation Fail

The Epic Negotiation Fail 36
Pinterest

Everyone knows that when people say to put an offer on the table, the word table is just a figure of speech. It's too bad that this person didn't realize that when they tried haggling prices for the washer and dryer. What transpired as a result was one of the most embarrassing, forehead slap moments in negotiation history. But hopefully, they were still able to buy what they wanted at an affordable price.



She Doesn't Know Her Flags

She Doesn't Know Her Flags 37
Reddit

The cool thing about social media is that people can add little icons and emojis to their posts. For example, when Kelly wanted to show her support for Donald Trump, she posted what she thought were three American flags in front of the name "TRUMP" and three American flags after it. Unfortunately, the icons were so tiny, that she didn't realize that she had used the flag from another country by mistake. And then someone pointed out her mistake for the whole world to see.



Christian Was His Name

Christian Was His Name 38
Twitter/@sahar_bear

There's a reason why people should avoid naming their kids after a famous religion. You just don't know when it's going to cause confusion like the time a lab partner introduced himself by saying "I'm Christian." Naturally, his lab partner assumed he was referring to his religion, so she figured she'd share that she was Muslim. But eventually, she realized much to her embarrassment that Christian was his name.



Cop Crosses The Line

Cop Crosses the Line 39
Twitter

This Twitter user asked whether someone was breaking the law if they crossed the white line at a red light. Naturally, the police noticed the tweet and responded to him by saying that yes it was a traffic offense to do this. And the user's response was epic when he posted a photo of a police van doing exactly what the police on Twitter posted that drivers shouldn't do.



The Subway Speech Impediment

The Subway Speech Impediment 40
Twitter/@BlackwatchPunk

This Twitter user confessed to one of the most embarrassing experiences she ever had at a Subway fast food restaurant. But it had nothing to do with spilled drinks or realizing that she had forgotten to bring her wallet. No sir! It turns out that she had a momentary speech impediment that caused her to pronounce a meatball footlong sub in the most awkward way possible.



She Hit On Her Dad By Mistake

She Hit On Her Dad By Mistake 41
Twitter/@baileyalexaaa

A Twitter user by the name of Alexa thought she was sending a NSFW message to her boyfriend. But as it turns out, she had sent it to the wrong man in her life—her father. Unfortunately, she didn't realize that she had done this until several hours later. And when she went to check her phone to see why her man hadn't gotten back to her, she discovered why and had to apologize to her father for being such a naughty girl.



The Mystery Of The Avocados

The Mystery of the Avocados 42
Twitter/@MavenofHonor.

For weeks, her friend had been very upset because he felt like he was under attack by someone in the neighborhood. There was no other way to describe what he had discovered in his yard. It seems that the attack had come in the form of avocados which a neighbor had been throwing into their property. But as it turns out, there was no disgruntled neighbor attacking him. In fact, the attack was coming from his own home.



He Passed Gas At The Gym

He Passed Gas at the Gym 43
Reddit/wellthatsucks

It's not uncommon for people to pass gas when they're doing some form of exercise, like leg presses, at the gym. That doesn't make it any less embarrassing though, especially if a beautiful woman happens to be passing by at that exact moment. That's something that most guys hope will never happen to them. Unfortunately, it did happen to this guy, and it's a safe bet that he did not have the courage to ask that woman out afterwards.



She Forgot Her Dog

She Forgot Her Dog 44
Twitter/@KlondikeBrat

Generally, when people go to the veterinarian, they remember to bring the most important thing with them—their pet. But that wasn't the case for one lady, according to this Twitter user. It turns out that this woman got all the way to the front desk at the vet to check in and suddenly realized that she had forgotten to bring her dog with her. Hopefully, she's not as forgetful when it's time to feed her four-legged friend.



Please Keep Me Updated

Please Keep Me Updated 45
Reddit

Some people thrive on bad news as long as it has nothing to do with them or someone they love. So when this person received a text about a guy named Jake who got burned in the worst place possible, this person immediately pointed out that they texted the wrong number but were interested in knowing more. And even after the texter apologized, this person kept pushing for more updates.



Strangers Celebrated Their Breakup

Strangers Celebrated Their Breakup 46
Twitter/Nxoyii

This guy learned the hard way that breaking up with someone should be done somewhere private like their place or their girlfriend's place. But that didn't happen. No. He decided to invite her to a fancy restaurant where he could wine and dine her before breaking her heart. But because the restaurant patrons saw her crying, they started celebrating because they thought they were happy tears.



Nice Eyes

Nice Eyes 47
Pinterest

This person was on a dating site where she matched with a guy named Michael. Luckily, Michael seemed like a nice guy because he started out by complimenting her on her nice eyes. Then she fudged it all up and made it weird when she gave him a sarcastic response, apologized for it and then started dissing her own eyesight. Looks like Michael should have swiped left on this one. Oh well! Maybe next time she'll get it right.



The Library Convo Fail

The Library Convo Fail 48
Pinterest

Tripping up on words is a lot more common than people think, and it can lead to some embarrassing moments. Take this person for instance. They took their time to rehearse what they were going to tell the librarian because they had a fine that they needed to pay. And by the time they got to the counter, they messed it all up and said something so embarrassing that they overpaid and decided never to return to that library again.



His Name Was Not Steve

His Name Was Not Steve 49
Twitter/@_rachjd

This Twitter user confessed that she had lived next to her neighbor for three years. She even had dinner with him and was invited to his apartment for a chat. She also thought that his name was Steve, but as it turns out, she didn't know him as well as she thought she did. But even though she messed up his name, she wasn't too far off because the guy did live with someone named Steve.



Her Boyfriend Embarrassed Her While Shopping

Her Boyfriend Embarrassed Her While Shopping 50
Twitter/@magsmathes

During a shopping trip, this woman's boyfriend decided to embarrass her by announcing loudly what he intended to do with the undies that she was looking to buy at the store. Naturally, everyone gasped in horror and the woman was admittedly very embarrassed. But then she recovered and served him with a quick witted comeback. Guess who will never try to mess with her ever again?



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