45 Texts That Are Almost Too Awkward to Read

That’s Just Plain Awkward

We’re just tickled pink that the screengrab feature exists so that we can all take a sneak peek into some of the world’s most awkward text exchanges known to man. Okay, yes — we’re being melodramatic over here but you guys are definitely in for some entertainment. So, grab your best snacks and get ready to cringe like never before…

Inside Voices

You know those nights when we get so inebriated that we lose all common sense? Well, Alex here was definitely having one of those experiences, which also explains why he was still up at 4:27 am.

Inside Voices

This over-served schmuck was so out of his right mind that he not only messaged himself but also then went on to reply. While we can all admit that we talk to ourselves from time to time, an inside voice is a different ballgame!

Granny Got Sass

While we know it can be difficult to try to remember all our family members’ and friends’ birthdays, it does come with the job of being a good person. Also, in the event that you forgot an important person’s birthday, don’t be surprised if you get a sassy message like this grandson rightfully deserved.

Granny Got Sass

We know we’re being a tad harsh since we’ve all been in his shoes but come on, your grandparents deserve better and it’s awkward that this granny had to practically beg for a wish.

A Betting Man

While we do not like getting one-word responses, Carmen took it a bit far with her comeback. Also, getting rejected is something most don’t respond too well to so we can’t really fault this dude for his lack of English words.

A Betting Man

Also, according to Urban Dictionary, “bet” is slang for words like “excellent” or “word,” so there’s nothing malicious about it. After close inspection of this awkward chat, we suggest that Carmen takes a chill pill and the guy on the other end should invest in a real dictionary.

Number Neighbor Challenge Gone Wrong

The number neighbor challenge was invented to cure loneliness and raise the community spirit flag high but unfortunately, this challenge comes with its own set of challenges.

Number Neighbor Challenge Gone Wrong

Check this chat out as an example of what we mean. While we feel slightly bad for the messenger as he couldn’t have predicted who he was texting, maybe he should take this as a lesson to stick to chats with people who he knows (and that are alive).

The Classic Pen15 Joke

While we can all enjoy the classic Pen15 joke, it gets too awkward when one tries to include one’s mother in it. Motherhood and male genitalia are two entities that just shouldn’t be mentioned together.

The Classic Pen15 Joke

It’s like trying to combine oil and water — it will just never mix. While we are well aware of how the baby-making process works, we just don’t feel it’s appropriate to be so provocative with a mother.

An Unexpected Message From IKEA

If you ever have received a text from IKEA, chances are it’s related to the delivery of your furniture, so we bet that Natalie was startled after reading this unprofessional message.

An Unexpected Message From IKEA

Not only that but this delivery guy’s (AKA Adam’s) forward nature is another red flag. Seriously dude? At least wait for her to respond and see if she’s remotely interested before asking her out. We suggest that he repents for this awkward situation at church.

Too Awkward for Facebook Messenger

We totally sympathize with anyone trying to find their parents but we just feel that this person’s approach here was too direct for such a serious matter. For starters, the opening liner is confusing as asking someone if they ran away could easily be misinterpreted.

Too Awkward for Facebook Messenger

Plus, the second message is just too invasive. We feel just as bad for the poor 21-year-old who was on the receiving end of this questioning. Luckily, he’s of legal age and can have a drink to calm him down from this.

An Open-Marriage

While open-marriages are not as taboo as in the old days, that doesn’t mean to say everybody is on board with them. So, when this married woman reached out to this dude, we can feel his hesitation about it from just a few texts.

An Open-Marriage

It’s highly possible that this woman’s arrangement does allow her to be open but we’re still confused about the last text — imagine saying that you and your husband are ‘just friends’… it’s just a tad bit platonic don’t you think?

Finding Nemo or Finding Love?

While fish are adorable and make for some of the greatest memes, if you’re trying to win back an ex then you’re going to need a lot more than this. Anything from a “hello, how are you?” text to a flower bouquet delivery would have been more successful.

Finding Nemo or Finding Love?

Even though the response was rude and to-the-point, we would probably also have said something along those lines. What did this dude expect?

Ouch, This Burns

There’s nothing like the visceral sting of rejection to make someone feel really bad about themselves and this chat hits the nail on the head of awkward rejections. It’s so blatant that the dude here was into this girl, so do you think it was necessary for her to mention her dating life?

Ouch, This Burns

We get if she wasn’t interested in him but rather say that than purposely overshare only to make him feel rejected. He’s going to need some healing forces from that burn. Poor kid.

An Unrequited Love

There’s little as painful as unrequited love. All that we hope for those lovers out there whose feelings are not matched is that they are let down a whole lot easier than this dude was.

An Unrequited Love

Don’t get us wrong, we understand and even kinda empathize for the one who just doesn’t feel the same but there is a much nicer way that this person could have gone about it. For example, she could have removed the cussing (like we did with the censors) and that aggressive tone.

Fishy Business

There’s nothing fishier than finding out your partner is cheating on you than through a delivery service. Plus, it’s fishy because of the choice in seafood (heck, we’re so funny we’re taking a pause to laugh at our own joke).

Fishy Business

But, in all seriousness, if Ariana decided that she couldn’t forgive Sai for their fight, then she should have had the decency to end things the right way. Not only does she not deserve that expensive shrimp lover’s combo, but she certainly doesn’t deserve Sai’s love.

Name a Creepier Cashier

We’ve all had those unfortunate encounters with questionable cashiers at the grocery store but this text chain takes awkward to another level.

Name a Creepier Cashier

This cashier managed to get himself fired just to get this girl’s number and probably didn’t gather just how creepy that is before sending the message. We highly doubt that Rachel engaged much further with him since invading her privacy like that is a pretty serious offense.

The Bling Ring

While we are well aware that our subheading is also the name of that heavily disappointing movie about high schoolers who rob celebrities, it also happens to perfectly fit the scenario here. Just look and admire that gorgeous rock for a second…

The Bling Ring

Now, once you’re done counting the carrots you should read the chat because it’s fabulously awkward. Derek took the classic ‘give me a ring’ line literally and we’re really impressed by his humor. We would go as far as to say he could be potential marriage material based on it.

A Deceptive Candle-Lit Dinner

When we see the words ‘romantic dinner,’ we often associate that with candles, a fancy table-setting, and all those romantic aids, so we were surprised by this chat. Quite frankly, we’re on board with the woman who responded with rejection.

A Deceptive Candle-Lit Dinner

If we were carried off our feet with this seeming romance only to discover a garage — we’d kindly excuse ourselves from the date and make a run for it. Plus, we’d probably block this garage owner’s phone after, so kudos to this chick for being nicer than us.

We Want Updates Too

While sending messages to the wrong number all too often ends in the most awkward of conversations, this particular one didn’t but we still had to share it with you all.

We Want Updates Too

Jake’s burnt behind was the topic of conversation that caught the attention of the stranger on the other end to the point where they wanted to remain updated on the fiasco. We guess nowadays all it takes is a fire under someone’s hiney to spark up a conversation.

Not Appropriate Over Text

We usually have harsh words to say to the kids who send rude or inappropriate texts to their mom or dad but in this case, the parent deserves the punishment. While the cartoon that the child sent was lame, it did not warrant this person to have to receive the news that his/her grandmother died over text.

Not Appropriate Over Text

This parent takes the cake for having the worst bedside manner in history when it comes to letting someone know that a relative has passed away.

Maximizing Efficiency

We have to give it to this heartbreaker of a woman who decided to be efficient about breaking up with all the guys she was dating — she added them all to a group chat and sent one explanatory text.

Maximizing Efficiency

While she has more courage and audacity than us to be serial dating so openly, we’re surprisingly impressed. However, we also have to emphasize the awkwardness of being on the receiving end of this mass message. Better luck next time guys!

Taking a Toll

Auto-correct has definitely become a major bane of our technologically-advanced messaging existence — especially as it seems to mess up horribly at exactly the worst time (Murphey law, probably). This work text exchange is a particularly awkward case.

Taking a Toll

This certainly would have been a case of “too much information” if Donna was over-sharing about her bathroom usage. Thankfully, she really wasn’t. But, this still created an incredibly awkward situation for everyone in the group.

Super Rude

It’s one thing to be honest about accidentally super liking someone but this Graham character took it too far with his explanation. This chat took place on the dating app, Tinder where you can swipe right if you like someone and even super like if the person is really appealing to you.

Super Rude

In Graham’s case, he ‘accidentally’ clicked the wrong button and justified it by saying that he actually would click the “super nope” if there was this option. How rude? No wonder you’re single and on a dating app, Graham!

Color Us Embarrassed

Everything about this text interaction screams awkward — from how this married man found this woman’s number through his wife, to the fact that he thought he could score a date with his obscene story.

Color Us Embarrassed

The only thing that makes sense was his last line because he should be severely embarrassed by this. We’re just glad that this woman screen-grabbed this chat and now it’s available for public viewing. We wouldn’t even be surprised if she named and shamed him. Quite frankly, he deserves it!

Hannah Is the New Herbie

While people are known to treat their cars as humans, it’s a tad surprising when you see companies do the same. In this chat, if you were to remove the word “vehicle” from Service King’s first message, most people wouldn’t even know that this is all about a car.

Hannah Is the New Herbie

Even though this exchange is on the cringe side, it does reminds us of the love we had for our favorite childhood movie character, Herbie. Both Herbie and Hannah deserve a buff, polish, and shine for making their owners so happy!

Knock Knock

Nine out of 10 times if we were to see the words ‘knock knock’ appear on a chat, we would assume it’s the start of some lame and embarrassing joke. Surprisingly, in this case, the awkwardness works well for Mr. Romantic over here.

Knock Knock

He chose the classic joke as a way of asking his crush the ultimate question — if she wants to be his girlfriend. Luckily, she appreciated the joke and took him up on the offer. We guess romance today is all about cheeky little jokes, heart emojis, and memes.

Killing Us Softly

This text interaction will most probably leave you bitter about the kids of today. We do understand that fewer conversations now will take place in real life but the actual content in some of these chats is where the problem lies.

Killing Us Softly

For example, this anime fan chose to convey his/her actions to the recipient by using asterisks. This phrasing is not common in chat rooms because… well, it’s just downright weird. Plus, we can’t seem to get over the petting line.

It’s Raining Peanuts

Grab your popcorn and sippy cup drinks for this one everyone, as things are about to get cringe. Here we witness this emoji-user trying to be provocative and talking about how he wants to send a snap of his private parts — which he displayed through a peanut emoji.

It’s Raining Peanuts

The girl responded by correcting him on the inaccuracy of using that emoji and the awkwardness just continued from there. We have some advice for frisky people like this dude, stay off your phones!

Delivery Girl

While we often see the awkward texting from the delivery guy, this encounter turned that stereotype on its head. Now, we have the customer hitting on the hot delivery girl, and here comes an added plot twist… both parties are married.

Delivery Girl

So, nothing about this scenario is in good taste, except for the fact that luckily the woman still has her morals in check. As for the married guy whose situation is “changing rapidly” — we suggest you legally change your marital status before doing this.

The Bra-Stealing Mom

There’s nothing more special than the bond between a mother and daughter because it often resembles a sisterhood before the mother chooses to pull rank as the authority. However, in some cases as seen here, the daughter could very well be the more responsible character.

The Bra-Stealing Mom

Here we have the bra-stealing mom and the uptight daughter, featuring this funny image of the mom in the stolen bra. We prefer these scenarios because let’s face it, they provide great comedic entertainment.

Mr. Romantic

While there’s nothing particularly wrong with this chat and we do welcome kind compliments, we just feel that Sebastian went overboard with it. His messages remind us of lines from some high school chick flick, where the male protagonist is trying to win over the female lead.

Mr. Romantic

Also, judging by the girl’s meek response of a sad emoji, she wasn’t exactly buying what he was selling. So, to Mr. Romantic AKA Sebastian, remember that we’re not living in a movie. Chill out with the dramatic expressions of love.

Officially Uncovered

Lying is considered a sin in some religions and perjury is a serious offense that can result in jail time. So, from that intro, we can definitely say that lying is no joke. However, that doesn’t stop silly people from being economical with the truth.

Officially Uncovered

From this screengrab, we can deduce that someone’s boyfriend lied about his whereabouts and even thought he had gotten away with it — until a bystander got involved and blew the case open. His staged Snapchat didn’t hold up and now he’s officially uncovered!

The Creepy Econ Guy

While economics is a great subject to study at school, no class is worth having to deal with creepers like this dude. He even had the audacity to take down a number that wasn’t addressed to him and message this girl.

The Creepy Econ Guy

His pompous attitude doesn’t end there — he then had the cannolis to ask her for inappropriate photos! We hope you’re as creeped out as we are because the day this stuff becomes normal, is the day we no longer want to live on planet Earth.

Uber Eats Coming in Hot

Not only does Uber Eats have spicy foods available on their app, but they also pack on the spice in their message responses. We were left humbled by their wit in response to a customer asking if they were at the main entrance.

Uber Eats Coming in Hot

In the client’s defense, that question is very common but truth be told, where else would they be if you put in the correct location? Also, the helicopter one-liner is priceless because Uber Copter actually exists.

Boys Are Distractions

This dude went from being romantic and cute, to considerate of the fact that the girl wasn’t interested, all the way to trying to marry her. If we were in the woman’s place, we’d block his number and run.

Boys Are Distractions

Okay, we’re totally kidding but it is strange that he changed his tune numerous times in the space of one short text message. While we do agree with him that “boys are distractions,” we feel like his multiple personalities are even more distracting.

We’re as Confused as You

If the pace of this chat confuses you, we’re totally on the same page and for those of you who think this is normal, then you need a reality check. We understand that the typical introductions to conversations nowadays can get monotonous and it’s probably better to be more forward, but there’s still a line.

We’re as Confused as You

That imaginary line of social norms is put in place so that inappropriate messages like “do you want to see my body” are not seen as okay.

The Funny Guy

The dude with the green messages sure thinks he is a comedian with his “knock-knock” opening liner and confusing break-up and make-up messages. To all the jokers out there who think it’s cool to do this to someone, we suggest you find another hobby.

The Funny Guy

Maybe this guy can take up hiking, or surfing, or simply spend more time coming up with new content for jokes as his current iMessage banter is not fooling us.

Caught in the Act of Lying

We know the feeling of subtle rejection totally sucks but sometimes you just have to put your pride to the side and own it. Otherwise, you’re just a lying schmuck like this dude who sent the tactical “sent that to the wrong person” line to cover his tracks.

Caught in the Act of Lying

Too bad he didn’t break that message up because now we know for sure he’s lying. Remember guys, lying always has a way of catching up to you so avoid doing it at all odds!

Talk Is Cheap

Anyone who talks about how they’re going to make you laugh as opposed to just doing it probably isn’t that funny, to begin with. While we don’t condone being rude about others, we can’t help but cringe at the awkward nature of this chat.

Talk Is Cheap

It conveys the “talk is cheap” idiom, which basically means that it’s much easier to talk about doing something versus actually doing it. In life, we aim to be doers, not cheap-talkers (like this texter, no offense to burst his comedic bubble).

The More Nuggets the Merrier

We are a big fan of fast-food chicken nuggets but unfortunately, Emily’s mom didn’t have that same excitement when her phone autocorrected everything to ‘nugget.’ She was also quick to assume that Emily had pulled this prank on her…

The More Nuggets the Merrier (move somewhere else)

Anything is possible but we’re going to give Emily the benefit of the doubt here because chicken fingers are best when eaten and don’t have the bones to make for a great prank.

A Special Kind

It takes a special kind of person to not understand how to play along with a classic “knock-knock” joke but rest assured there are plenty out there. Take this texter here who responded with “yoooo” as opposed to “who’s there?”

A Special Kind

If we were the person trying to make the joke, we would have jumped ship and tried with someone else after getting that response. However, this joker clearly had more patience than us and carried on with the chat despite the awkward hiccup.

An Uber Therapist

Sometimes we all just need a little TLC (tender loving care) and we’ll take all the support we can get but with that being said, we really should check who we’re talking to before getting too personal.

An Uber Therapist

This person made that unfortunate mistake after realizing that she had started baring her soul to her Uber driver. If we were in her shoes, we’d cancel the trip to save us from what would otherwise be a very awkward ride.

Sierra, Be Serious

There’s nothing more embarrassing than witnessing someone trying to open their hearts to someone else who’s so not on the same page. That was the case for this poor soul who was trying to have a serious moment with Sierra.

Sierra, Be Serious

Unfortunately for him, Sierra was more concerned about finding Oreo cereal than working on their relationship so we think it’s best that this hopeless romantic finds love elsewhere.

What a Lame Excuse

Listen up, we’ve all been in situations where we’ve not been that interested in someone and have had to come up with a polite way of saying it. However, this cat excuse is pretty high up on the list of lame excuses.

What a Lame Excuse

This person should put their grown-up pants on and tell the person who’s asking for a date that they’re just not down. Honesty is key in these situations. Otherwise, you just look like a crazy cat person and most likely, a liar.

A Weak Slang Game

While we love our moms more than anything, that doesn’t mean to say they know everything. In fact, in some areas, they’re absolutely clueless, especially when it comes to adapting to the digital age. Slang acronyms like ‘IDK’ and ‘TTYL’ at this point should be familiar to all texters and phone users.

A Weak Slang Game

So, when this mother responded to her one child with such confusion that she thought she needed to enlist the help of her other child, we couldn’t help but laugh. We recommend she gets educated on her text slang ASAP.

The Queen of Sass

Being sassy via text is nothing new to witness but when the sass is being directed at someone’s boss, then it has our full attention. This Bread Co employee had the audacity to tell her superior who needed her at the restaurant that she’ll get there “whenever.”

The Queen of Sass

If that wasn’t bad enough when he answered that she was already 20 minutes late for her shift, she came back with the ultimate sass queen picture.

Two ‘Carrot’ Ring

When we see the words “two carrot ring”, despite the misspelling of karat, most would still assume it’s referring to a diamond ring and a very good one at that. Awkwardly, this texter here was actually referring to a ring with two carrots on it which the text recipient didn’t get until a picture was sent to clear things up.

Two ‘Carrot’ Ring

No offense to the ring-wearer but we’d rather have no ring at all than one with carrots. Remember, karats or nothing guys!

Baby Shoes

We love a good wrong number text chain, this next one was not well-received by the other party who threatened to bring in the police. Unless we’re missing a backstory or other texts leading up to this screenshot, we don’t quite understand why this would warrant the cops.

Baby Shoes

Then again, the image of the babies in the shoes is peculiar and gives us some creepy vibes. Also, who purposefully sends that to a stranger? A psycho, that’s who!

We Can Feel the Heat

Chatting to an ex will not end well nine times out of ten. It’s likely that the two parties will see things differently and want opposing outcomes. Such was clearly the case here for this texter who wanted to compliment his ex-girlfriend’s looks post-breakup.

We Can Feel the Heat

She didn’t exactly have positive affirmations to give back to him as her saucy response indicates that their split was the catalyst for her make-over. Given the heat she fired back, we’re just going to assume the dude messed up and deserved her comeback.

Dad Wants a Twinkie

We cannot think of a single thing funnier than an inebriated parent. Don’t believe us? Just read this text encounter between an overserved father and his sober child. We’re calling this hilarious and nonsensical chat ‘Twinkie Gate’ because that’s all this dad wanted in his intoxicated state of mind.

Dad Wants a Twinkie

Also, calling his child “my little fluff’ as a term of endearment is in itself meme-worthy. This dad truly deserves his much-wanted twinkie.

That’s Not a Cat

While we understand that getting numerous messages from a wrong number is most annoying, that surprisingly isn’t what makes this text exchange so awkward. We can’t seem to get over the fact that the recipient of the images thought that this cute little dog was a cat.

That’s Not a Cat

Like, really? Even if you don’t know who the person is on the other end, it’s straight-up obvious that the animal in question is a dog.

Text Fail

One should never doubt the comedic power of autocorrect. It has gotten many texters around the globe into some of the most awkward text encounters. This tweeter here posted about her own experience with it and we have to say that it’s one of the best we’ve seen in a while.

Text Fail

Her phone would always autocorrect the word ‘leaving’ to ‘lesbian’ so when she would try to write “I’m leaving now” it would come out as “I’m lesbian now.” That probably led to her having to provide some explanations to friends, family, and colleagues. Talk about awkward!

A Stranger’s Kindness

Most often when we show you wrong number messages, it ends in awkward banter or even someone attempting to bring in the cops. That’s why we wanted to show you a merrier text exchange between two strangers that warmed our hearts and might even be featured on The Ellen Show.

A Stranger’s Kindness

When this texter, Jordan, accidentally informed a stranger of his whereabouts, the recipient told him to “have fun” as opposed to the usual “who’s this?” or “get lost” responses. Talk about a nice guy!

Watch Out for Autocorrect

This mom made the ultimate autocorrect faux pas by mistakenly alluding to the fact that she and her husband wanted alone time for ‘adult cuddles’ to her daughter. As awkward as the idea of our parents doing the deed is, we need to remember that it’s totally normal and how we all came to fruition.

Watch Out for Autocorrect

As for the mom here, she should double-check her messages so that her daughter doesn’t need to think about that uncomfortable topic.

An Autocorrected ‘No’mance

Leave it to autocorrect to make a normal chat sound beyond awkward and inappropriate like in this case. However, we weren’t born yesterday and we know that this new generation of texters have, shall we say, ‘colorful minds.’

An Autocorrected ‘No’mance

So, we’re going to bet that autocorrect was a cover-up for what these people actually wanted to say. Whatever happened to love letters and chaperoned dates? What a time to be alive.

Mum Needs to Chill

If you read this chat through quickly, it appears as if mommy dearest has two personalities because she went from love and kisses to anger and cursing in one day. We have a few suggestions that could help alleviate the awkward nature of this conversation.

Mum Needs to Chill

First of all, the son needs to work on his hygiene (respect the tea towels!) and secondly, the mother needs to take a giant chill pill (or even some anger management classes).

An Overprotective Girlfriend

While it’s awkward when other girls get overly friendly with your boyfriend on social media, there are also clear boundaries of what’s allowed. For example, his friends, family, and colleagues (if he’s a working man) are most definitely allowed to interact with him.

An Overprotective Girlfriend

So, this girlfriend here has no leg to stand on with the level of sassiness she’s displaying to her boyfriend’s relative. In fact, she owes the cousin an apology.

Grandma’s Arms

Oftentimes when we try to text too fast, we end up making errors or misspelling words. Our miscommunications can sometimes make no sense or in the funnier cases like this one, it can just sound majorly inappropriate.

Grandma’s Arms

In this texter’s case, instead of referring to her grandma’s arms, she mistakenly wrote about another body part that let’s just say, granny wouldn’t have been pleased hearing about. However, she did make amends by letting the recipient of the message know that autocorrect had gotten the better of her.

Get Your Facts Straight

There’s nothing more irritating than aimless texting that goes in circles but from time to time, we all manage to get ourselves in chats like this. Though, what we don’t commonly experience is dealing with someone who seems to have full-on amnesia.

Get Your Facts Straight

Just read this chat here to understand what we mean — was this person perhaps joking? Judging by the formality of the rest of the messages, we’re gonna say no. Awkward much?