Cringey Texts That Are Way Too Awkward to Read

Communication has changed a lot these days, for better or for worse. Email, text, and apps galore dominate the social and professional lives of millions. And with so much digital chat, it’s easy to be misunderstood! Sometimes, it’s no big deal. But it can absolutely awkward, too. The graphic options on SMS don’t help! 

When people try to be honest in emojis, there’s a lot that can go wrong: Who hasn’t had a tense moment or two, for no good reason? It’s time to take a look at the very worst text exchanges out there. Screengrabs preserved the cringe, in its truest form!

The Car That Cared

Swipe and go, they said. Under-five minutes, they claimed. Remember the days before instant transport? That’s right, nobody does! Here, one user ordered a quick ride. Or did they?

Life can be rough. Conveniently, with Uber, Lyft, Gett, and more, there’s no need to schedule anything ever again. But it seems someone here might really be looking for a friend. Or at the very least, a therapist!

Dead End DM

In the early days of the internet, people privately enjoyed a new activity. Anonymous chatrooms were places to connect with strangers all over the world — and for free! But since social media has spread, there is a lot less of this secretive behavior. Real question: What’s going on here? 

Breaking boundaries, one weirdo decided to text whoever had a similar number. Why? Never ask why. The tale did not end well, as it shouldn’t. Surprise, surprise: The owner of the phone died a long time ago. Number neighbors, forever!

Kiss Kiss Bang Bang

The teen years be a bit strained, between mom and daughter. It’s a time for youngsters to test boundaries, and try new things all on their own. That can be challenging, in itself. But here, one gal gets the tables turned on her. And it’s gross, ew!

Are nightmares a likely outcome here? Yes and yes again. A typo can be worth 1,000 yucks, and this one is no exception. Hang or bang: It makes all the difference in the world. Mom quickly retracts her comment, but the damage is done!

I Sea You

The sea is full of monsters these days, big and small. According to trusty old Encyclopaedia Britannica: ”Squids have elongated tubular bodies and short compact heads. Two of the 10 arms have developed into long slender tentacles with expanded ends and four rows of suckers with toothed, horny rings.” Erotic, yes?

Apparently, one ex was not impressed seeing this critter on her phone. The message came in just in time for lunch: Glub glub, please take me back. But she didn’t, and she won’t. Some say it’s the thought that counts!

Don’t Stalk Me Bro

Checking out at the grocery store is becoming increasingly automatic. Self-checkout is popular. And then there’s the fear that robots are going to replace so many jobs, someday. For this worker, that day hasn’t arrived yet. But still, he has been let go. How did his employment end, against his will?

It’s hard to say for sure. Maybe he was late a few too my times. Or maybe, just maybe, it was all the stalking, using private customer information. How did he get this woman’s phone number? Not with her permission, that’s for sure!

Just the Two of Us

With apps to sort through thousands of names and faces, it can get a bit overwhelming. How is a girl supposes to organize all her matches at once? And with so much flaky behavior out there, should she date only one guy at a time? 

Some of these questions have no clear answer. It’s easy to make others feel expendable, in the cold, automated process. Here, one gal tried to avoid hurt feelings. She sends a detailed explanation about her single status. But tech-savvy she is not: Including all her matches in the message didn’t flatter anyone!

Family Matters

Bonding with grandparents a very special memory, for most people. Childhood can never have enough cookie baking and storytelling. And there’s nothing like wisdom, from the old days! But here, a message exchange reveals an alarming fact about a little one’s last visit. What in tarnation is going on here?

Grandma’s arms would be the reasonable place to fall asleep. But here, it seems the situation was a bit complicated. Was autocorrect to blame, or did the truth come out? People do blame technology for a lot of mistakes, these days!

Refusing the Hint

Love is a precious thing, and few find it. Many are looking for love in all the wrong places. The wise Helen Keller once said: ”The best and most beautiful things in this world cannot be seen or even heard, but must be felt with the heart.” This is not one of those things. 

On a routine delivery, one driver thought he might try to enhance his reward. Sure, he already got a tip. But maybe he could also pick up a mistress — a married one, willing or unwilling! 

Bait and Switch

There are challenges in online dating, and memory is one of them. One problem with texting multiple girls is keeping track of the romance. Who is who, and what is going on? Embarrassingly, mistakes happen sometimes. Like this guy, right here!

A summary is needed. First, he texts her. Then, he says he is surprised to be hearing from her, out of the blue. But he isn’t, and she points out the obvious. At this stage, he may as well be messaging himself, all alone. Where this goes next, nobody knows!

More Drama Please

Time for an understatement: Burns are a bummer! Whether the tissue damage is from heat, sun, radiation, electrical contact, or chemicals, it’s always a letdown. Here, it sounds like Jake has set an intimate part of his own body on fire. Not once, but twice now!

It sounds like it’s been pretty chaotic, over there. But there’s a twist: All this information was unsolicited. Nobody was asking! It was interesting as a surprise from afar, though, via SMS. Why not send the updates? No one likes a tease, after all!

Lost and Found

In the best scenarios, single moms try their best. Still, wishing dear old dad was around is not unexpected. In some families, it’s hard to make that happen. One grown-up boy with an internet connection is on a mission. What’s the plan?

A very general one, actually. Maybe it was a mass message to all the dads in the area. Maybe it was an honest mistake, with a very common name. But in any case, the search will need to continue. The 21-year-old here is not the man he needs!

It’s Complicated

Wishy-washy is no way to succeed in love. It’s a good idea to be direct when it’s time to get a date. Women love an assertive fellow! Here, one female texter follows that advice. It’s still legal to ask a man out, isn’t it?

A lot of boundaries are being broken behind that keyboard. Not just traditional roles, either. This lady wants to go on a date with a single guy, but she isn’t so single herself. Who’s the man in all the pictures? Just her husband. No big deal!

Scheduling Conflict

Honesty is not always the best policy, right away. Sometimes, a guy wants to say so much on his mind. It can be hard to hold back — but it’s best to compliment a girl’s eyes or smile, most advise. This texting Romeo has followed all the social conventions. Will he get the attention he craves in return?

No, he gets a summary of her better date options. She has plans already, and it all begins tomorrow night. After work, all bets are off. And no, they don’t know each other!

Mystery Man

Yum, yum, yum. Crawfish and shrimp could be a sensual afternoon. But since Ariana is home all alone, she will just have to enjoy it by herself. Sent by insta-delivery by her man after a fight, it’s sure to mend things right up. But what’s this — her little brother has stopped by?

Well, that can’t be right. Ariana’s an only child! Why is a man hanging out at her place, away from watchful eyes? Sometimes, the truth hurts. And sometimes it comes from the takeout driver, unwillingly caught up!

He’s Got the Goods

Ikea has become a beloved shopping trip worldwide. They dominate the first apartment decor niche, for good reason. With trendy Scandinavian designs and low price tags, everyone goes home happy. The only trouble is the delivery, after a big trip. Luckily, the megastore offers that, too!

At first, everything seemed like standard Ikea protocol. But then, a message appeared the next day while Natalie was trying to figure out all the blueprints. Delivery dude Adam says hi again, and he wants to see her romantically. Is this the new VIP service, or what?

Me, Myself, and I

Alex is a busy guy, and sometimes she likes to check in with his mates. What are they up to, and where are they right now? All good questions. But this time, Alex asks Alex. Is that what he really meant to do? Readers may not be sure, and neither is he!

Are you in town? Nah mate, I’m home now. Who did he think he was writing to? Maybe this is a drunk text, and he will come to his senses tomorrow. If not, it’s time to ask a few hard questions!

Come Here, My Pretty

There are reasons people keep cats and dogs around. Petting them has a lot of benefits! According to WebMD: ”It can lower your blood pressure, helps your body release a relaxation hormone, and cuts down on levels of a stress hormone. It also soothes your pet.” Sounds soothing, indeed.

Here, there’s some confusion about the act. It’s human to human! A new love interest is trying to apply the principle. Simulating a few strokes online, the creep factor shoots through the roof. Wild stuff! Who couldn’t resist this invitation?

Introducing Airdrop Delivery

Sometimes it’s a bit jarring to get an SMS from a mystery number. Who could it be? A good question, for anyone who values privacy. But when an Uber Eats bag is on the way, isn’t the sender obvious? Somebody placed that order!

Drunk food is a pretty big chunk of business, for these apps. But that has its challenges. Waiting around is not profitable! When asked who he is and where the pickup location is, this worker goes sarcastic. The helicopter pad isn’t used a lot with Uber deliveries, so far!

The Kids These Days

Riddles and brain teasers are a great way to bond with the family. All generations can enjoy a mind puzzle, when the occasion arrives. Here, one kid has decided to try some sort of word math challenge with mom. What’s the real point, though?

The idea is simple. Just add pen4 to pen5. Then, don’t forget pen6. What does it all mean? Mom tries to use traditional addition to solve the problem. But she finds out the truth, the hard way. This dirty game was never about math at all!

Pee-ka-boo, You Know Who

They say that men evolved to make women laugh, and women evolved to have a sense of humor. Is that all really true? In this case, there might just be an exception defying the trend. One strange dude keeps promising his signature humor. But is the lady receptive?

Seem not, in this case. Something is missing from his style, maybe. Promising that a woman will wet her pants isn’t the most sensual threat. Most would probably scream, face to face. She doesn’t seem to be the exception to the rule, either!

He’s So Pun-ny

Knock-knock jokes have a proud history in the field of laughs. And why shouldn’t they? The format is easy to follow for amateurs and experts alike. And there are so many ways to make it work! Here, one fellow decided to weaponize the old method for love. How did he do?

In a rare success story, a cornball won the day. Knock knock. Dooya wanna be my girl? Why, yes. She does! The joke worked exactly as planned. It was a longshot, many will say. But he who dares, wins!

Stealing the Digits

Mysteries can be thrilling as a movie or book genre. But when it comes to real life, that is not always as true. One girl applies that idea to her text messages at 2:49 am. Who is contacting her, and why?

It’s not good news. The SMS come from someone she never gave her information to in the first place. It seems he has gone out of his way to get it, disturbingly. Were bribes involved? Did he beg? All in all, this mystery was not intriguing enough to stick around. Bye, she explained!

Under Her Hood

Cars, trucks, and SUV’s all have their fans. But for most drivers out there, a vehicle is just a way to get from point A to point B. For a few, it’s a lifestyle. Everyone knows someone a little too obsessed with their machine!

In this case, the driver even has an idnetity for his car. Hannah the car? It doesn’t have a memorable ring to it, truthfully. But people have their reasons, and it’s hard to judge. Service King had no plans to do so, living up to the essence of their own name!

Swiping Sadist

Tinder, Bumble, Hinge, and back again. To the left, to the left. And suddenly — to the right! In a neverending stream of singles, it’s great when a profile truly stands out. Here, all the stars have aligned. A super-like has occurred, against all odds. The girl even makes the first move!

But the cruelty comes right away. The like was a mistake, and the guy is not interested at all. He doesn’t hold back with the truth, either. Maybe there’s a reason girls wait for messages and not the other way around!

Cheaters Never Prosper

Everyone has their good days and bad days. It’s nice to get a compliment sometimes, even from a stranger. As long as it’s sincere, a well-placed remark can be day-changing. That rule doesn’t apply to married men, of course. PSA: When it’s the husband of a friend, it’s not welcome at all!

Asking for it in a pretty sloppy way, isn’t he? It’s not like the messages are encrypted. He claims to be embarrassed about it all, but is that true? Maybe the wife can answer that question best, ASAP!

Three’s a Crowd

The world of sports has something for everyone, and boxing certainly has its fans. It’s simulated fighting, and that can be a real thrill! Admittedly, these events draw more men than women. But does it have it be that way? That all depends on the generous invitation, right here.

Three’s a crowd is often cited as a reason to stay home. In this case, the lady is merely booked for Amsterdam already. It sounds like she would be open to it, in theory! But wait — it’s the wrong recipient. Offer invalid. Awkward much?

Tutti Frutti Cutie

Impressing the ladies with a fresh joke is a skill few men really master. Here, a texter is in hot pursuit of a cutie with a knock-knock joke. She doesn’t seem to understand the flow, though. Can this even succeed, if only one person plays along?

Helpfully, he holds her hand along the way. Virtually, that is. After successfully teaching her the mechanics of the knock-knock, he delivers the punchline. The answer is honeydew? At this point, there’s no communications issue. He’s just not funny, with this format or not!

Diamonds Are Forever

Call me, call me any, anytime, sang Blondie. The song really had a point. It’s no fun left to wait by the phone, all night long! In this case, the demand came via text. And the gal was proactive, demanding a chat on her terms. What did she get for her efforts?

Apparently, a play on words. And a digital diamond ring, right away! It’s not the way most proposals happen. But maybe modern times call for modern solutions. Try a lazy text with a picture of a gem. And don’t hold back making the most of a pun!

Slang Game

Dating is a long process for those looking to land a forever partner. Sometimes, a night goes well enough, but things don’t click beyond dinner. How did this gal let her suitor down, in the end? As SMS receipts show, in a pretty mature way.

She had a really nice time, admittedly. But she doesn’t want to continue. He responds with strange slang, causing her to google the term. “Bet” seems to be a nonchalant term the cool kids use these days. He didn’t seem to care, and that stung!

An Offer You Can Refuse

Love is an inspiring thing, at its best. Some people spontaneously write poetry or songs to express their feelings. What’s going on here? In middle school, these letters were common. But adults rarely communicate this way. Do you like me? Check the box, yes or no!

Oddly, this person doesn’t seem very inspired at all. In fact, he expresses a very dour mood! He likes her, sure. But when asked to explain why he feels that way, he just cites loneliness. He ruins it for good with that next line if there were any doubts. Thanks but no thanks, buddy!

All’s Fair in Love and War

Arguments between ex-lovers can get pretty nasty, at times. It can be hard to remember why each party admired the other, back when it all began. Here, two star-crossed haters exchange barbs. Bad taste and low standards, the SMS war begins! How will it end?

Well, it ended fairly fast. Maybe she did have low standards, at one time. Maybe she even had terrible taste in men. It happens to the best of gals! But adding it all up, things don’t look flattering for the ex. He really dug his own grave here, verbally! Score: 0 / 1.

Green, Shmeen

Hearing from Reed is always a treat. This time, the greeting comes right after lunch. What a pleasant surprise, Reed! It seems he just wants to confess that he has been missing his lover’s eyes, far away as they are now. Seems pretty romantic, right?

Something strange is going on here, though. The green eyed beauty seems to have been mistaken for another girl, altogether! That, or Reed was color blind, throughout the whole relationship. It is more common in men, after all. But did this message miss the mark? The internet reports, readers decide!

Across the Universe

You are my sunshine, my only sunshine. You made me happy, when we were once together. That’s how that old song went, right? One guy probably thought so. But when his text was greeted with this astronomy metaphor, things took an unexpected turn.

Does he want to be the sun in her life? Yes, for sure! He just has to go more than 92 million miles away, and then he can be just that. A long trip, sure. But it seems hard to have such a long distance relationship, which might the point!

Talking vs. Stalking

Shakespeare’s Romeo once explained: “My bounty is as boundless as the sea, My love as deep; the more I give to thee, The more I have, for both are infinite.” Unrequited love can be a painful experience. It’s a timeless challenge in literature and life!

But equally painful? Running away from a weirdo! This texter just doesn’t give up, and he does eventually get his response. It probably wasn’t the outcome he dreamed about, though. They dated for a few months, almost a decade ago? It’s time to be rational, and give up!

Twenty Thousand Leagues Under the Sea

Natural disasters often bring the community closer together. Even fighting couples in the storm can get over petty grudges, when life and death come into focus. Today, this is not that pair: Just a friendly check in during all the flooding? No thanks, buddy!

Joey feels it was pretty cold to ask who he was. After all, he was someone special at one point to this person. But today, things have changed. Along with the flood water, this connection seems to have washed away. Face the facts, Joey: The relationship is underwater!

Back to the Future

Timeless wisdom would advise: “Tis better to have loved and lost than never to have loved at all”. Many live by the rule! But here, one ex might just not be ready to accept the idea. In fact, they haven’t gotten the memo about the breakup protocols. No more phone!

In the spirit of openness, they express dismay that the texting rate is not what it used to be. The response? A clarification about the increasing electronic distancing. Communication is key, after all — and exes aren’t supposed to be doing it, silly!

Good Day, Goodbye

Hello, is it me you’re looking for? No? One dude found out the hard way, after a simple greeting. He merely asked how her day was. She explained the situation, which he accepted. But it probably wasn’t what he was hoping to hear!

The disappointment is easy to hide behind a screen, and there’s plenty here. According to the recipient, things were a-okay until around 3:15 pm. But then, things went south. What happened at that moment? Simply put, she heard from her ex. Nobody wants to deal with that after lunch — or ever!

Lonely Lover

Sometimes, distance makes the heart grow fonder. Sometimes, distance hardens it into a black, shrunken piece of coal. One ex found out the hard way, as seen in this failed attempt to rekindle the old flames. Long time, no talk? Let’s keep it that way!

There’s no mistaking the response, here. She’s just not that into him. Not anymore, not ever again. Why reconnect after so long, out of the blue? Maybe time has faded his memory, but there’s usually a reason people completely stop talking. This harsh reply might just jog his memory!

Snapchat Chump

Modern messaging services offer a lot of privacy options. Some people are still quite open with their online presence, with friends. But that might be a mistake, in this case study of ex texts. Taylor is online, so it must be a great time to reconnect!

Tay was just online trying to figure out the block feature on the app. More of them should have one, frankly. But it just so happened that an old love was watching her every move while she did it here: Each finger stroke, a sign of hope. This time, the assumption was wrong!

Spelling Bee Champ

Look, punctuation is not a moral issue. Most people will let it slide, unless they are total grammar Nazis. But today, the error in the ex text goes a bit deeper than a spelling slip up. For such a deep feeling, this one is surprising!

Jamie was the best thing that ever happened to this girl. Every creature loves to hear its name, with positive affirmations. But in her attempt to communicate this to him, she makes a big mistake. The relationship sounds like it was full of them, too. Better luck next time, lazy!