Too Awkward For Words: 35+ Painfully Blundering Exchanges That Are Cringy

By Liezel L

Remember that time when right after you said or did something, you just wanted to put a foot in your mouth and have the earth swallow you whole while you’re at it? Yeah, we’ve been there. Texting the wrong person? Check. Talking to someone we’re not really sure we know? Of course. But those are just mild. We can immediately forget those in a day or two. The more embarrassing ones have us wishing we could wipe ourselves from existence even for a few seconds and erasing the memories of all the witnesses to our blunder. The only saving grace is that we are sure we’re not alone and that some people actually have it worse. If we do get the ability to wipe certain moments of our lives, we’d want to share them with these poor folks after we get a few laughs in, of course. Get ready; it’s about to get really embarrassing here. 

What Happens At The Dentist Stays At The Dentist

Going to the dentist is an awkward enough experience most of the time. Moments there range from your dentist finding a piece of lettuce between your teeth to them chatting you up and asking you all kinds of questions while your mouth is wide open. Still, there’s room for more awkwardness. 

image courtesy of Tiger Aspect Productions and xtinanovakovic/ Twitter

To be fair though, whenever dentists do that, it does indeed look like they’re going in for a hug. And after one particularly nasty appointment, especially if a root canal was performed, it’s easy to mistake it as a sign of comfort.

What We All Want To Say To Our Teachers

Most students don’t ask teachers for help. Sometimes, it’s out of our own pride, and other times, it’s because we don’t really feel we can approach our teachers. No matter the reason, we do often wish we could have been this straightforward with our teachers. 

image courtesy of CBMSt1/ Twitter

What makes this message a lot funnier, though, is that it’s so vague. The professor won’t really know what his student is worried about and why in the world would they have to be involved. Are they worried about lessons? Or are they worried their professor isn’t living up to their perception of him? Either way, it can induce a crisis of major self-doubt. 

That Fart Incident

Farting in public is probably one of the hardest missions we all have had to go through at least once in our lives. The first thing you have to consider is the sound, and the second thing is the smell. Most of the time, though, no one has time to think about any of that. We don’t want anyone to know. Sadly, for this dude, he just had it all wrong. 

image courtesy of Facebook

To be fair, he did have a decent plan. It was very well thought out, and it was smart since after disguising the sound, he can easily get away with the smell. Sadly, it all backfired in the execution area. 

Crush Fail

Embarrassing moments with crushes are a classic. We just want to be our charming best selves in front of them but alas, that never seems to be the case. It’s like whenever we set out to impress them, we end up doing the opposite thing.

image courtesy of meganlewis74/ Twitter

The situation still would have been savable by trying to act cooler than you really were but let’s be honest, after realizing our mistake, we would have been too ashamed of ourselves to even think about trying to do anything else. 

Happy Pup

We all have those moments when we walk into a room or go out only to completely forget what we were supposed to do or get at our destinations. Oftentimes, we’re able to remember it by backtracking our thought process but then there are times we get there too late. 

image courtesy of Karsten Winegart/ Unsplash and klondikebrat/ Twitter

This woman was probably on automatic pilot mode except her brain skipped out the most vital part of her trip in the first place, the “grab the dog” part. As it seems, she made one pup absolutely thrilled that day. 

That’s Rough Buddy

One of the benefits of online dating is that you most likely will never meet or even see the person you swiped left on. It means fewer confrontations and less awkward conversations on why you think it won’t work out. There are golden moments when this happens, though. 

image courtesy of Red Table Talk and Twitter

We don’t know who it hurts for more, the guy who was technically swiped left on right to his face or the person who so mercilessly did the swiping. Then again, there are plenty of possibilities yet for these two. We never know; maybe this could be the start of their great love story, a painful rejection to the face. 

A Furry Muffin?

It is easy to mistake any tiny adorable creature for a stuffed toy, especially those ones with big shiny eyes and especially if they’re being carried around by their human in their arms. You’d have to take a long second look to confirm if it is indeed alive and breathing. It also happens the other way around. But we’ve never heard of it happening with food before. 

image courtesy of hdurant/ Twitter

We might be able to understand if the OP mistook the hamster for a muffin. We could brush that off to extreme hunger or being under the influence, but for them to mistake a muffin, a MUFFIN of all things, for a fuzzy little animal, we’ve got some questions. We completely understand if the owner of said muffin backed away slowly until she was a good distance away. 


You know, we can forgive whatever weirdness happens on Mondays. That day is just a different kind of moment for almost everyone. From saying goodbye to fun and weekends to go to school to saying goodbye to rest and peace to go to work, many people have a certain hatred for Mondays. That’s why this guy gets a pass. 

image courtesy of leelucascarrie/ Twitter

His statement is pretty accurate for a Monday, too, rather than anything he could have said. Even if it is just for a second, a little tender hug could do wonders for us to be able to get through the nightmare we call Monday. 

Did They Make The Sandwich Though?

Home is where we are often our most authentic selves. We walk around in our worst unshowered forms; we act in our most unfiltered ways, and so much more. That’s why it’s understandable why we don’t usually expect strangers to be walking around our homes like this person. 

image courtesy of Disney and mirrortraffic/ tumblr

If it were us, we would have been so mortified as well. We should be the ones making them sandwiches and not the other way around. What would our mothers and grandmothers say about our manners? As Mushu might have said, dishonor on you and dishonor on your cow. 

Wrong Place Man

Coffee can solve a lot of problems. It can help keep you awake at school and work while tipping you closer and closer to palpitations. It can also keep your mind sharp in the busy afternoons while also pushing your anxiety to its highest levels. At times though, coffee just isn’t enough.

image courtesy of kaynecaraway/ Twitter

As hilarious as it is, we get it, though.  Sometimes, for some of us, it’s not enough to just stay awake through the day. We need a little something extra to help us get through all the annoyances of the day without harming anyone or ourselves. 

A Classic Breakup Fail

There is never really a right place for a breakup, although arguably, there are worse places to do it. For instance, people generally frown upon nonpersonal breakups like calling or texting. Still, some situations can be just as bad as this one. 

image courtesy of Nxoyii/ Twitter

For some reason, people sometimes assume that when a girl starts crying when she’s having dinner with her guy, it’s a happy kind of crying, and they start responding like there’s some kind of celebration. But next time, maybe it’s better to wait for the hug or the shout of joy before starting any congratulatory actions. 

That Moment When Your Password Gives You Away

It’s always hard to think of a new password that is hard enough not to get hacked but easy enough for you to remember. That’s why a lot of us resort to using the same passwords over and over again. Those security questions do work, though, unless you won’t be able to remember the answer to those questions or something like this happens. 

image courtesy of Skelly401/ Twitter

We do wonder, though why, of all security questions would you choose something as risky as this? We get that it’s personal, and only you’d know it, but then the bigger question becomes, why is that the one thing you want to be forced to remember when you forget your password? Do you really want to go down that road again?

Just Being Polite

Confessing your admiration for someone is insanely hard but just imagine someone with who you don’t share the same feelings with doing the same to you. It’s a different kind of difficult trying to rebuff them and not hurt them at the same time but then imagine it coming from a stranger. Creepy, right? Well, not unless you’re the stranger. 

image courtesy of Tiger Aspect Productions and ryanlangdon_/ Twitter

You gotta hand it to the guy though, saying I love you too to a total stranger just because he wanted to be polite takes some guts and a whole load of confidence. Hopefully, he did get to use those guts and confidence with someone who will reciprocate it. 

Better Luck Next Time

When you don’t like someone, you first have to keep it all to yourself, especially when you live or work with the person. After all, talking behind someone’s back isn’t really a great thing to do, but then when you find someone with mutual feelings, the relief is a godsend. Oftentimes though, you have to be very careful, or something like this happens. 

image courtesy of ilovehentai/ Twitter

We’re not sure if the blue bubble person is really referring to the other person, but either way, it’s not something they can easily apologize for. Seriously though, one of the primary rules of talking behind someone’s back is to double-check first before sending. That’s how you don’t get caught like this. 

Someone’s Hungry

When we’re starving, our brain generally shuts down and only allows thoughts about food to filter in. Everything looks like food, everything smells like food, and everything even feels like food. No matter what it is, our brain develops the ability to make it all about food just like this guy. 

image courtesy of 9gag

For someone who got a perfect 59 out of 59 on an exam, it must have taken some form of extreme hunger for their brains to go that foggy so as to mistake their perfect score for something that looks like salsa.

8 That Time When Food Became Scary

Food is great and all, but do you remember all the times it caused you to have a bad stomach, for you to start feeling that rumble in public suddenly, and for the sweats to start soon after? It wasn’t so great, was it? That’s why we kind of get this person. 

image courtesy of twitter and tuftyfrog/ twitter

Soup is great for warming up cold souls, but it’s not exactly great when it’s too hot. Maybe this person was just rushing to warn the other guy of the hot soup, but then his mouth wasn’t able to catch up to his brain, and oops, there it goes. 

Oh, Wrong Advice Dear

It’s one of the most awful things to be the third person in an argument, especially when it’s between two people you know. It can turn pretty bad real quick if you try to interfere, but when it’s between strangers, it can turn catastrophic. Take this unfortunate incident, for instance. 

image courtesy of raquelhinkson/ Twitter

As good as her intentions might have been, the results of her interference were less than diplomatic, and she might have just ended up making one person a lot more furious and the other a lot more humiliated. We don’t think anything can compare with how mortified this girl is, though. 

The Library Pee

One way a lot of us cope with the anxiety of human interaction is by creating a script for ourselves and trying to memorize it. Sometimes, it works, and we get off not looking like a complete weirdo, and well, sometimes, it just flips, and we expose ourselves for who we truly are.

image courtesy of Walt Disney and ifunny

This is why those little practice sessions aren’t worth anything. Once our sensors detect the presence of the human to whom we don’t want to look like an idiot in front of, it just shuts down and throws the script out the window. Then, we end up with something like this. 

The Best One Yet

See, there is awkward stuff that gives you major second-hand embarrassment, and then there are awkward encounters that just makes you wet yourself with laughter. This one, for instance, is the prime example of that human idiocy that pops up in all of us from time to time. Some just have it worse than others. 

image courtesy of sendsnacksplz/ Twitter

This guy’s logic failed him at the worst moment and in the worst possible way. Much like that TSA guy, we would have lost it too. Forget being decent to another human being, we would have rolled over on the floor laughing at him in the face.

We Don’t Want To Miss Out!

People are weird and hospitals get a good dose of that weirdness every single day. You would get people with coins in their stomachs or buttons or even wrenches. But that’s just mild considered what some people would do to their bu&*holes. 

image courtesy of

First off, how dare they cut off this precious piece of interesting conversation. We also want to know any updates but more importantly, we want to know why in the world would Jake set his butthole on fire. It is not something we can just let go of!

Karens Are Out Again

If you’ve never met a Karen, just go to your local mall, pick any store, and look for that typical middle-aged woman asking to see the manager for apparently no other reason than to complain about some tiny little thing and walla, you spotted a Karen in the wild. This person had it better, though. He was on the receiving end of a Karen fit. 

image courtesy of noahforchange/ Twitter

Seriously though, what did Brittney do? What is this alleged stunt, and why did she do it? And why is the cul-de-sac barbecue so important that this banning feels a little harsh? We need to know all the juicy details! But wait, hold on, does all this unnecessary curiosity about a stranger’s business bring us closer to being a Karen too?!

Never Trust Automated Messages Again

There are people who get genuinely anxious when they hear the ping of a message, we included, especially when it’s our bosses calling about a deadline or our parents texting us when we know we’ve done something wrong. That’s why automated messages are a godsend: no obligations, no worries, just plain information. 

image courtesy of nudey/ Twitter

No one usually tries to respond to automated messages. It’s probably the only message we can leave at seen without feeling the least bit of guilt. When boredom strikes, though, we get how fun it can be to just mess with it, not unless it isn’t an automated message after all, of course. But really, of all things, “peepee poopoo?”

A Minute of Feeling Flattered

A little flattery is good. It can make us feel a lot better about ourselves, especially when we have been going through some rough times. Sometimes though, you have to make sure that what you hear really is flattery and not part of a meal order. 

image courtesy of Nickelodeon and i/ twitter

Still, though, we’d take this kind of mistake more than those people who assume you like them or would like to bang them just because you looked at them. Compared to that, this situation is just plain adorably hilarious. 

The Fart Cone

What is it with farts? They’re a natural bodily function and they happen to everybody. Even if you were the queen of England or even if you were Tom Cruise, you’d still fart. And yet, even fully grown mature adults like us still laugh at something that doesn’t even remotely concern farting but just mentions it like this. 

image courtesy of unclewhiskysrevenge.tumblr

A fart cone. For some reason, that sounds like an actual object or a natural occurrence. Maybe in an alternate universe, it’s what they call the bags where royals point their farts towards, or maybe it’s some kind of thing that can be created with farts. Try letting your imagination run free with it. 


Some jobs are just more vulnerable to awkward situations than others, and most of those are food industry-related jobs. On the one hand, you get the couple with the crying girl who is either getting married soon or breaking up, and on the other hand, you get the random birthday of a dead person celebration. 

image courtesy of rachel_bonacci/ Twitter

In these kinds of situations, though, we feel a lot more sorry for the person who made the mistake because how in the world would you or they have known that the person was dead? They do work with people, but that doesn’t mean they have a radar for dead loved ones. 

Great Conversation Starter?

Some people don’t get why other folks would create social media accounts for their pets, and those are the people we don’t get. What’s wrong with wanting to share your pet’s dorkiness or cuteness with the world? Then, again, something like this could happen. 

image courtesy of Billard24/ reddit and kateleeex/ twitter

If that guy were worth it, though, he’d be pretty thrilled to discover a cute hamster account. Sure, getting a message from a hamster would be weird, but hey, it’s a great conversation starter once the hamster’s owner gathers up the balls to admit their mistake, of course. Our advice, if that guy doesn’t appreciate the hamster, dump him.  

Oh, That Is Just All Kinds Of Pain

Surprises are both fun and not fun. See, a surprise free spa day from your best friends is super fun. On the other hand, a surprise diarrhea call of nature in the middle of an important meeting is not fun. Still, there are worse surprises than that. 

image courtesy of

This is equivalent to the person you’re sleeping with calling out the wrong name in bed. This one is not right in the face, but it might as well have been. Poor guy must have also been so excited to surprise his girl but he ended up getting the surprise instead and in the worst possible way ever. Hopefully, it doesn’t put him off surprise romantic gestures forever. 

The Unintentional Dad Joke

As much as we don’t want to admit it, there are some hilarious dad jokes out there that aren’t as embarrassing as all other dad jokes. The key is to say them in the right situations. Otherwise, it’s just cringy. For this unfortunate lass, their mistake seems like a dad joke gone wrong. 

image courtesy of Marvel and sahar_bear/ twitter

Of all things in the realm of introductions, why would she think that the first thing he, a stranger, would reveal about himself would be his religion even before his name? Doesn’t it work the other way around? Anyhow, at least they got that right out of the way. 

Kayak Bags

Our workplaces can sometimes turn us into mindless robots that automatically do as we were programmed from the first day we walked into the place. And then, when our human part finally drifts back into our bodies, we discover that we’ve just committed another blunder we can’t easily forget. 

image courtesy of s_rumer18/ Twitter

If we were the customer and we were feeling kind of evil that day, we would have probably said, “Yes, please.” We might have even offered to help them look for a bag we can stuff the kayaks in. If the guy did find a bag, we’d be pretty freaking amazed, and we’d probably give him a large tip. 

Completely Professional 

Have you ever noticed how ridiculously too formal work emails get sometimes? Even when two people are arguing via email, they still strive for the utmost formality, and it becomes a contest of “Please see attached..” and “With all due respect” statements. It drives us nuts sometimes, but this dude clearly knows how to deal with the “standards” of formality. 

image courtesy of adam_karpiak/ Twitter

This guy has the perfect response to this “no smiley” face edict, and just the gal on him has us chuckling in devious laughter. Seriously though, who doesn’t want smileys on emails? Smileys make everything less dull and threatening. What’s wrong with that?

Completely Deserved the Judging

It’s almost always irrational, but whenever we go down the wrong turn or the wrong road, this sudden fear of getting lost springs up, especially if it’s a route we never usually take. There’s GPS and all that, we know, but still, our mind just likes to frighten us, so we get this guy, sort of at least. 

image courtesy of Disney and greatestgoth/ tumblr

Strangely enough, even though we can’t even begin to explain how he got to “quack” from “quick” and “fast,” it makes sense. Unfortunately, no matter how great he explains it to the driver, we doubt he’ll get it. Maybe he was a duck in his past life?

When the Psychiatrist Messes Up

Ah, therapy. It’s supposed to be a safe place where you can admit everything and anything. Mortifying or not, it’s the one place you can expect not to be judged, openly, at least. What happens if it’s your therapist that commits a blunder, though?

image courtesy of 2earsandaheart/ Twitter

Oh, the cringe. Fortunately, the client took it way better than expected. It makes us wonder, though, do therapists have therapists as well or confidantes who they can talk to about things like this? It’d be pretty amazing if they can keep such blunders to themselves. If it were us, we need someone to suffer the cringe with us.

Cheating With Shopping Maybe?

There are varying types of jealousy in a relationship. There’s the adorable type that makes you want to squish your partners like they’re a cute little puppy. There’s also the type that’s just downright manipulative. And then there’s the type that endears you and still sort of makes you question why you’re in a relationship with that person. 

image courtesy of crlockha/ Twitter

The guilt trip is strong with this one, and the best part is he is totally obvious about his jealousy. The dude can’t even try to hide it if he wanted to. His reply at the end is what seals the deal for us. Hopefully, he came up with a good way to explain all that the next time they do see each other. If it were us, we probably would have taken him to Michaels just for the kick of it.  

The Sacred Cup

Dentists do give people with prosthetic teeth cases for them, right? And yet, for some reason, older people still love using cups to hold their teeth. No wonder finding a set of teeth staring back at you when you just wanted a drink at your grandparents’ house isn’t that rare. You’re lucky if you find it early, unlike this chap. 

image courtesy of Twentieth Century Fox and Facebook

It’s fine if it was just a one-time mistake, but they’ve been using it not for days, not for weeks, and not even just for months, no. They’ve been using it for years! Have they never really noticed anything off with it? Have they never looked inside of it? They’ve been gulping down and washing their mouths with grandma’s teeth soup for years!

Some Ears Need Cleaning

When it comes to accents, it doesn’t matter if you’re speaking the same language as the person you’re talking to. There will always be moments when you completely get something wrong. The problem is when there’s no turning back from your blunder. 

image courtesy of guelphgirlchris/ Twitter

“Liter” and “leader” do sound pretty close, but how in the world did they all get it wrong? One person making a mistake is forgivable, but for the whole group, that’s just questionable. They even talked among themselves without even wondering why in the world would she be asking for a leader. 

What Reward Exactly?

Much like how we shouldn’t just give our addresses to anybody, we also shouldn’t just offer our numbers to anybody either. Creeps can get pretty damn creepy even in text messages. So this girl was in the right state of mind but maybe not in the right situation. 

image courtesy of xineliza/ Twitter

Is there any way you can recover from such a situation? We’re not sure there is. As smooth as you are with words, the damage has been done, and you have been immortalized as this assuming idiot stranger in that guy’s mind. If anyone can, we’d love to take lessons to make our lives a little less humiliating, please. 

Is This A Kidnapping?

Imagine this. You greet someone with “Have a great day” or “Keep safe” or anything like that, and you don’t even get a nod. It sucks, right? All those wasted words for nothing. That’s probably one of the reasons why a lot of us are programmed to say “you too” to all these greetings and pretty much everything else. 

image courtesy of Twentieth Century Fox and klondikebrat/ twitter

In this situation, however, it’s downright embarrassing. The cashier might assume it’s some lame form of flirting. She could also assume you’re just out of your mind. The worst-case scenario is she assumes it’s a threat, and you’re attempting to kidnap her. 

That’s What You Get

We can never understand how people with multiple partners can muster up all that energy to shower all those people with affection and keep them by their sides. We can’t even muster up enough energy to engage in a bit of human interaction sometimes. All the same, this is a prime example of how people like this majorly screw up. 

image courtesy of reddit

This is not the best example to learn from, but it does provide a great scenario of what to avoid and why it is important always to check if you’re sending your message to the right person before pressing send. Thank heavens for the person that called them out on their BS. 

Poor Mother

You have to appreciate it when the older generation starts trying to get in with the younger generation’s slang. It shows they care, and they just want to be able to understand and communicate with the kids better. Sometimes though, they just don’t get the right teachers for it. 

image courtesy of gracel721/ Twitter

You have to appreciate the mom’s creativity in using that phrase, though. She made it sound so normal, like it happens every year. Imagine it like “Don’t forget to wear extra belts today, or somebody’s going to get your a*s.” Or “Damn it, it’s a*s eating season again. Gotta stock up on those extra undies.” 

The Grape Curse

Grapes are great fruits. First of all, they’re delicious. Second, they have a bunch of stuff like antioxidants and vitamins that help lower cholesterol, blood sugar, blood pressure, and so much more. Its seeds are tiny as well that’s why we couldn’t really understand why anyone would use it as a threat.

image courtesy of

Those grapes even look nice and juicy. What did the person really expect to happen? That the person they should have sent it to would get scared by the grapes’ green coloring or that he/she would choke to death on those sumptuous things? We need to understand.