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Text Messages That Are Almost Too Awkward to Read

HizkiailAugust 11, 2021

Holding a candle

That first crush in high school can hit us pretty hard, and be really tough to get over. It’s the first time we’ve dealt with love and feelings and all that comes with it. While most of us can probably remember our first love, however, generally we have long since gotten over the joy or disappointment that went along with it.

Not this guy. Not only does he still remember his first love, but he’s decided that contacting her every year to remind her of their week of romance is cute and not creepy at all. I really hope that her response, blunt as it was, gives him the shock he needs to start living in the present, and not 6th grade.

Crossing a line

Here we have another example of how invading someone’s privacy can end pretty badly for you. Rachel wasn’t expecting a text from the cashier at the store she’d visited earlier that day. Thankfully, she knew just what to do about this major crossing of a line, and she didn’t hesitate.

You might feel a little sorry for the cashier, but can you imagine how clueless he must be not to realize that taking Rachel’s number from work and texting her without permission was a firing offense? Hopefully, he’s learned his lesson, and Rachel has struck a win for all single girls everywhere.

Garage date

First dates are wonderful things, a messy mix of apprehension, excitement, and enthusiasm. You never know quite how they’re going to turn out, but usually, the mention of a romantic dinner conjures up a particular image in your head. You may be expecting a lovely restaurant or a cozy night being cooked for.

If the reality turned out to be a picnic table set up in a garage, then you’d probably be quite disappointed. Tucking into steak and vegetables surrounded by power tools and a truck isn’t really my idea of a good time. It obviously isn’t this woman’s either and well done her for not wanting to do it a second time.

Keep me updated

Wrong numbers can be annoying, and sometimes they can be unintentionally embarrassing. Every once in a while, though, you come across one that is both shocking and hilarious. In this case, a simple text to let your partner know that your child has burnt their behind ends up going astray.

The person on the other end of the line obviously has no idea who you are, or who Jake is, but they’re definitely intrigued by the way the story is going, and they want more information. Well, who wouldn’t want to know what happened and how a child managed to injure themselves in this way? I’d be hooked.

Group message dumping

Busy people always need to find ways to make their lives more efficient. Time is short, and we all have a lot going on, so sometimes multitasking is necessary. Usually, however, when it comes to affairs of the heart, even the busiest of people will go for a more personal approach.

I didn’t think that it was common practice to send out template dumping messages, but I’ve been proved wrong. This enterprising woman has decided that dumping 4 people is far too time-consuming and that a group message could get it all done in a fraction of the time. She’ll go far, I think.

Creeping around

Here we have an example of why women assume that most guys on the internet are creeps. Sure, not all men would consider doing this, but enough of them see the light of day for us to be dubious about a man’s intentions when they get in contact with us. There are so many things wrong with this exchange that I don’t quite know where to start.

Firstly, the only reason he knows who this woman is is because he’s been checking out his wife’s profile. So, he’s married. Then, he managed to get her phone number from somewhere. So, he’s creepy. Lastly, he’s contacted her out of the blue to ask if she wants to start an affair. So, he’s a dirtbag. I hope she tells his wife about this.

Car love

I used to date a guy who called his car “Caroline”. Yes, it was as weird as it sounds, and he used to spend far too much time washing and polishing her for me to see a future with him. I guess that the good thing about this exchange is how happy and helpful Service King’s employees are.

The weird response from the customer reminds me of my ex, though. Fine, call your car a name and feel affection for it on your own time, but no-one needs to know that you miss it when it’s at the garage being serviced. Keep that weirdness to yourself.

Mr. Romantic

It must be tough being a guy these days. Every pick-up line invented has been heard a million times already, and approaching a girl to ask her out can be intimidating. Doing this via text isn’t really any easier, except you don’t have to worry about what to wear during the exchange.

This guy has obviously decided to go down the “cheesiest approach ever” route. It really is a cheesy line, but she seems to have quite liked his corniness, as she takes him up on his offer. I think these two will be very happy together, binding over corny jokes and Star Wars gifs.

Beyond weird

Propositioning the object of your affection via text message doesn’t always work quite as well as that, though. Especially if you’re just that little bit too weird about it. Not only does it take a while to work out what is actually going on in this text message exchange, but once you have, you’ll feel a bit gross.

It’s not just the sheer amount of brainpower that is needed to understand what they mean, it’s the petting line that is the most off-putting. Why would they think that was an appealing way of getting someone’s attention? It doesn’t seem to be going down well, so I think they better try something else.

Changing rapidly

We’ve had the delivery guy hitting on the customer already in this rundown, and here we have a reversal of that position. The customer is hitting on the delivery girl in this exchange, and the messages just get weirder and weirder. Firstly he’s a little miffed that she doesn’t get right back to him.

Then, once she replies that she is married, obviously to put him off, he is not cowed. He wants to have some fun with her anyway. Then finally the kicker is that he’s married too, but that’s “rapidly changing!” So, we have another dirtbag; who would have thought?

A bit much

Most people love an unexpected compliment as they go about their day. Being told that you have nice eyes, or that someone loves your shirt can put a little bounce in your step and get you through a tough afternoon. There’s an art to the compliment that keeps it on the right side of creepy.

Sebastian has gone far over the line with his three messages. Perhaps the first one would have been ok, although to go straight in with “You are so beautiful” is pretty strong. Then he doubles down with an assumption about her self-esteem, before finishing off with a sentence straight out of a romance novel. I’m not surprised he got a sad emoji face.


Let this screengrab be a warning to you, lying will always catch up with you. Even if you think that you’ve covered all of your bases, got yourself an alibi, and staged a good photo cover-up, all it takes is for one person to see you where you’re not meant to be, and the game is up.

As in this case, the boyfriend had gone out of his way to make sure that he wasn’t found out. He’d even made up a fake Snapchat photo so that his girlfriend thought he was with his parents. A mutual friend makes a passing comment, and suddenly someone’s having a serious conversation this evening.


Adoring someone from afar is an integral part of the school experience. Who hasn’t sat at the back of a class and gazed at a beautiful girl or guy, wishing they had the confidence to walk up to them and ask them out? It’s the plot of every romantic comedy, for goodness sake.

This is not the answer to your predicament, though. This creepy guy from econ class decided that he could take the number the girl gave to another guy as an invitation to ask her out. As she quickly points out, that’s not how this all works, and she’s probably not going to be interested in him now.

Perfect sarcasm

I like a cheeky server or delivery guy. It shows that they don’t take themselves too seriously, and I know that it helps them make their day more interesting. No-one wants a bored and grumpy Uber Eats driver dropping off their burger and fries, do they? Well, in this exchange someone is feeling the sarcasm.

As cool as it would be for Uber Eats to start employing helicopters in their food runs, it’s probably not a practical solution in any location that doesn’t have helipads or large open spaces. Also, prices would definitely go up. I can’t help but laugh at this guy’s response, though.

Autocorrect strikes again

There was a time a few years ago when it was the ultimate prank to grab your friend’s phone while they weren’t looking and change the language to Spanish or Mandarin. They wouldn’t be able to read it, and so couldn’t navigate to the menu they’d need to change it back. Many an hour was spent messing around with that in my youth.

The more recent phone-based language prank? Using the autocorrect function so that every time your friend, or in this case your mom, types a particular word it comes up as something else. Here we can see that Emily has lovingly made a word in her mom’s phone turn into nugget and her mom has no idea what is going on. I wonder how long this went on.

Too close for comfort

We live in a time where being open about your feelings is considered a healthy way to live your life and look after your mental health. This is great, and long may it continue, but it does sometimes have unforeseen consequences. Take this particular exchange, for example.

It’s always nice to get a message like this first one, knowing that your friends are looking out for you during hard times is a great thing. Unfortunately, by jumping to conclusions about who might be texting him, this guy has opened himself up for a very awkward ride to the airport, or wherever he’s off to.

Cereal craving

It can take a lot to reach out to someone you’re no longer with and tell them you miss them. If the breakup was mutual, or perhaps reluctant, then you never know what might happen. That little message might start the relationship back up again, and you’ll both be happier than before.

Or, your ex could not be interested at all, as in this case. I quite like the fact that Sierra didn’t jump in telling her ex to get lost. She decided to change the subject, and hopefully make it clear in a kind way, that he was barking up the wrong tree. Oh, and that she really wanted Oreo cereal.

Protect the cat

The new “I’m washing my hair” excuse? It’s definitely “my cat is sleeping on me.” I love this exchange. The winky face emoji makes it clear that he’s keen to meet up. He’d like to hang out with the girl he’s texting this evening, and he’s confident enough to think that she wants to hang out with him too.

I think he might be overestimating their connection, though, because between going out with him, and staying exactly where she is with a warm cat sleeping on her legs, she’s choosing the latter. At least she’s being honest and I sympathize. There are days when I don’t want to go out either, and I don’t even have a cat!

Keeping mom cool

Parents are supposed to be embarrassingly behind the times, it’s practically part of the job description. You’re supposed to be able to have a conversation with your friends using slang and have your mom ask what on earth you were talking about. Some parents, however, are desperate to keep modern.

This mom, for example, has obviously seen some acronyms written in a message or on a web page, and really wants to know what they mean. Unfortunately, even though her son very kindly explains them to her, she seems to have gotten the wrong end of the stick. I wonder how he’s going to talk her through it.

New bling

Misspelling something via a text message is a ridiculously common occurrence. It usually takes me a few minutes to work out what on earth my brother is actually saying when he texts me, with all the typing mistakes in the message. If he used the word “carrot” when talking about jewelry then I’d assume it was a mistake.

That’s just what the recipient of this message did here when her friend told her about a new ring. I would also have expected to see a decent-sized diamond in the photo that followed. I definitely wouldn’t have been expecting 2 decorative carrots attached to a gold band. I guess it is pretty cute, though.

Creeped out

Wrong numbers aren’t always welcomed as warmly as they were by the guy who wanted to know about the burnt behind. Sometimes people jump straight to legal action, and for absolutely no reason at all. Except for being slightly creeped out, if they’re anything like me.

I have to admit that this photo of “baby shoes” isn’t one that I enjoy looking at. I don’t know why, but dolls really freak me out, and these are especially creepy. Even so, if I received the photo from an unknown number calling the cops would not be my first move. I’d probably just chalk it up to a wrong number and move on with my life.

Moving on

Speaking of moving on, I am head over heels in love with the respondent to this Facebook message. Staying in touch with your exes isn’t usually a good idea Sure, sometimes you can stay friends if the breakup was amicable, or if you’re just a very big person, but usually, it ends badly.

I’m taking this as advice for the next time that someone I’m done with contacts me. The creeping message about how good she looks was obviously meant to spark up a conversation and maybe meeting up again. She is having none of it, however, and replies with all the sass that I wish I had in my life.


As well as being generally embarrassing, and unable to handle modern-day communication technology, and slang, parents can sometimes raise the bar a little higher. This is especially likely when they’ve been indulging in one too many white wine spritzers. They can become demanding, and a little annoying.

In this case, Dad has the munchies, and he’s not giving up easily. Even when his son tries to let him down gently, he decides that using many nicknames, and invoking Mustafa is the way to get what he wants. I don’t think that Dad is getting his twinkie today, and he’ll be pretty embarrassed in the morning.


Usually, when someone sends a message to a wrong number, they realize their mistake, apologize and then stop sending texts. This individual doesn’t seem to know when to give up. He’s not even answering when asked who he is, and is just sending photos again and again.

The funniest thing about this conversation, however, isn’t the persistence of the photographer. It’s that the recipient honestly thinks that the photos he’s being sent are of a cat. I get that chihuahuas can look a little scrawny, but it’s pretty clear that they are dogs and not cats, right?

Coming out

These days, thankfully, being open about your sexuality is generally pretty normal. Being gay is no impediment to work, life, or love in most countries, so fewer people have to worry about coming out to their nearest and dearest. This doesn’t stop what happened to this texter from being pretty embarrassing, however.

Autocorrect has struck again, unintentionally outing this woman to everyone she texted to tell she was leaving. I wonder how many responses she got and how she broke the news that just because her phone thought she was a lesbian, didn’t mean she was.

All the encouragement

Often a person texting a wrong number will end up with a “get lost” or “who is this?” I get that people have limited time, but there’s nothing wrong with being polite and friendly. Thankfully there are some lovely people out there who will take the time to connect with another human being, even one they don’t know.

Like here, where the recipient obviously had no idea who Jordan was, but decided to tell him to have fun anyway! It’s sweet, but I’m glad that Jordan followed it up, otherwise he’d think he’d let his parents know where he was, and they’d just be sitting there worried about him.

Controlling partners r us

Sliding into someone’s DMs when you know they’re in a relationship is clearly disrespectful, and their partner would have every right to call you out and ask you what you thought you were doing. No one is disputing that, but this is definitely not what’s happening here. Here, someone is overreacting.

Liking your cousin’s photos on Instagram is usually considered to be good manners, even if you’re not friends too. Here, the cousin is just showing some online encouragement, but the girlfriend is displaying some next-level protectiveness. If I were the boyfriend, I would be running away quickly.


Quite often I will have a whole conversation in my head and then start talking to my husband as if he heard the whole thing and should be up to speed. Needless to say, he gets pretty confused, and then I have to fill him in on what I was really thinking. In marriages, you get used to having to mindread, but this text conversation is weird.

I wonder what was going through the first person’s head between sending the message and receiving the reply. Did they get short-term amnesia? Did they fall asleep? The second person must have been pretty confused by the end of the exchange as well. Perhaps it would be better just to go away and chalk this one up to tiredness.

Mom the thief

Having a daughter can be hard work. You have to deal with mood swings, friendship spats, and working out how to plait their hair. You can spend months being the best of friends, only for something small to blow up and then you’re dealing with slammed doors and stoney faces.

Surely one of the perks is that you get to borrow their clothes? Or that’s what this mom thought when she was struggling to find a bra to wear with her top. She obviously thought that they were on good enough terms for her to raid her daughter’s closet. The response implies that she may have been a little optimistic.

I propose a deal

I don’t know whether Derek was playing around when he sent this final message. He may just be one of those annoying people who can’t resist a pun when it’s right in their faces. Or perhaps he just wanted to see what the reaction would be if he brought up the subject. We’ll never know.

I really hope that he was just joking, because a photo via text message is really not the best way to propose to your girlfriend. Also, what if he was joking and then she turned around and said “yes!”, what would he do then? It would be a pretty interesting story to tell your children, though. If they got that far.

Fishy ex

Here we have another example of how moving on from a relationship is a really important life skill. The level of interconnection that we enjoy in this technological society can be great for staying in touch with family or friends who live away. It does mean that, unless you change your number, every ex can still get hold of you.

In this case, they can also send you photos of cuttlefish. I have to say, this would be weird enough even if they were still dating. The fact that they broke up a year ago and a completely out-of-context cuttlefish is his message of choice tells me all I need to know about why they’re no longer together.

In search of dad

There are some people who perhaps dated a lot when they were younger, and every now and again run the nightmare scenario of a long-lost child turning up through their head. It would be quite a jolt to suddenly realize that you have a child you didn’t know anything about, out there in the world.

Facebook would probably be one of the worst methods to find out about it, though. Imagine reading a message from a stranger like this! Especially as no time frame is given until later on in the exchange. Thankfully it’s soon pretty clear that the numbers don’t add up. What a relief for the potential dad!

Birthday wishes

Sarcasm has its place in life as well as in text messages. Parents are especially good at employing it to make their kids realize they’ve messed up. “Thank you so much for putting all of your clothes away,” said in a wry tone whilst staring at a pile of washing is just a more interesting way of telling someone to tidy up.

This message feels a little bit too awkward, though. Sure, it’s a shame that his grandson didn’t contact him on his birthday, but I can’t imagine that the sarcastic message is likely to make him reply. He might just be thinking about how grumpy his grandad is now.

I made you

I love this message and the amount of sass that this guy’s mom can make the leap from the screen. We’ve all had to sit through parents thinking that they’re funny. Bad dad jokes are a rite of passage for any teenager, and who hasn’t had to deal with their mom trying to sit in on a conversation with you and your friends, trying to be young and cool again?

This is the proper way to enact your revenge, short, to the point, and devastating. It’s a bit like when your mom tells you to not show off in front of your mates. There’s no way back from that. And there’s no way back from this mom’s response, either. Well done Mom!

But it doesn’t mean…

If you’re looking for the perfect combination of a lack of street cred, and a lorry load of embarrassment, then we have it right here. Sharing the sad news of a family member passing away is a tricky text message to craft. You have a lot to convey in a short message, and you can’t always get across what you mean as well as you’d like.

When you add in using acronyms that you aren’t really sure of, then you get a really embarrassed mom like this one. Now she has to go back and call everyone she’s already informed that she wasn’t actually laughing at Great Aunt’s demise, she just doesn’t know what LOL means. I’m embarrassed for her!

A bit forgetful

Just after I’d been born, my parents were out shopping. They were carrying me around in my Moses’ basket, and my mom headed off to the post office quickly, leaving me with my dad in a music store. They met back at the car 15 minutes later, and I guess my dad wasn’t used to the whole thing because he’d left me on the floor of the music store by mistake.

Obviously, they came back and found me, but it does make me laugh when I read this exchange. This mom must have been pretty distracted to completely forget that she’d driven to the store with her daughter. I wonder how long she had to make it up to her for.

Not coming out

Supportive parents are worth their weight in gold. Knowing that they are behind you no matter what is key to building confidence and self-esteem. So, it is really lovely that Michaels’ mom was so supportive of his message. Unfortunately, it turns out they got the wrong idea, Michael’s not gay!

Of course, their reaction was just what he’d hope for if he was gay, but the most embarrassing thing about this exchange? It has to be the part where his mom tells him that they’ve always thought he was gay. Now he’s going to be doing a lot of trying to work out why they’ve come to that conclusion.

Making the big bucks

This exchange reminds me of the calls that my gran makes to me when she gets confused by her computer. She is convinced that if she presses the wrong buttons she’s going to break the internet. She’s also convinced that I know everything there is to know about computers, and can solve all of her problems. It can be a little annoying, but it’s also quite sweet.

Her misplaced confidence in me is nothing compared to this mom, though. Not only does she think that her son runs Google, which tells me she doesn’t spend a lot of time reading the news, but she also thinks that he needs to stop messing around with her computer! I wonder if Larry Page has a similar problem with his mom.

Not up to the task

It’s become quite common in the last few years for grown-up children to buy their parents a mobile phone. They want to make keeping in touch a little easier, and they also want to open up their parents’ world to the wonders of texts, Facetime, or just Candy Crush. It doesn’t always go smoothly.

In this case, the mom in question has bought her own new phone, but I think it’s going to take a while before her son gets a coherent sentence out of her. My gran texted me in capitals for the whole first month she had a mobile. It made me laugh a lot, and she didn’t understand what I found so funny!


Getting involved in your parent’s relationship as an adult child is a recipe for disaster. Some parents think that now their kids are older, they can talk to them like a trusted friend. This is usually great, but there are always some things that it’s best not to know about your own parents.

In this case, you don’t want to know that your mom spends time googling for photos of Johnny Depp’s butt. You also don’t want to know that she’s hiding it from your dad. You definitely don’t want it to be discovered that you helped your mom hide the google search from your dad. I think it’s best just to pretend you don’t know in this situation.


One of the main aims of a parent is to bring up your children to be respectful, caring and modern members of society. If you have sons then you, as a mom, want to know that they will treat women with respect, and talk about them in a way that you’d approve of, even once they’ve grown up and left home.

This is why this mom’s response is so perfect. Responding to her son’s casual misogyny, with the best burn is the perfect strategy. Hopefully, she addresses the disrespect that he showed and gets him to clear the cups from his room at the same time.

Failing at the internet

Once you have bought your mom or dad a phone and introduced them to text messaging, then you have to deal with being the IT department help desk 24 hours a day. Where do they click, how do they search, etc., etc. The funniest thing about this exchange isn’t necessarily that Andy’s mom thought she needed to put his email address in a text.

It’s definitely that she decided typing his name 10 times was what she needed to do to get him to pick up the phone, and then she called him a Grumpus! I mean, technically it did work: he did pick up his phone. I can’t help but feel as if this may take a lot more explaining for poor Andy, though.

Not helping

The idea of losing my phone actually gives me palpitations. According to scientists, we are all addicted to our smartphones, and researchers have found that we’d rather lose our wallet with all our money in than lose our phone. We’ve become so reliant on them that it would be tricky to live our lives without one.

So it’s nice to know that there are some decent people out there who will try and return a lost phone to its owner as quickly as they can. Unfortunately, this nice person has chosen the wrong contact on Adam’s list to help him. If Adam doesn’t have his phone, then texting him isn’t going to help matters. Aiden doesn’t seem like the brightest bulb in the box.

Too soon

When you have to deal with a sudden bereavement it can be difficult to think of anything else, especially your job. Rather amazingly, this individual managed to rearrange his work schedule for the time he would be gone, make sure he had contingencies, and let his boss know he would be contactable for emergencies.

All that is pretty impressive and any empathetic boss would have been mightily impressed by his efforts and offered him sincere condolences. To be fair, that was what this boss tried to do, but autocorrect wasn’t playing ball. Instead, he made what looks like a pun on death. It’s definitely too soon for those kinds of jokes. He must have been mortified.

Dating a worm

Sometimes, late at night when you’re trying to sleep, your brain makes odd questions pop into your head for no reason at all. What color would your mane be if you were a unicorn? Would you rather be chased by a horse-sized duck or 10 duck-sized horses? Why do clouds sometimes look like faces? That kind of thing.

It seems that this guy decided to ask his ex the answer to one of these late-night questions. Unfortunately, he didn’t quite get the response I think he was hoping for. Aside from how weird it is to ask someone if they’d date a worm, he also has to deal with the implication that he might not be the world’s best boyfriend. She doesn’t even let him down gently.

Fake number

For girls who get hit on a lot, it can be easier all around to use the fake number method of getting rid of them. Some men are so persistent (read: creepy and aggressive) that saying you’re not interested doesn’t work, neither does saying you have a boyfriend. It can be easier just to give them a fake number.

The positive side is that they go away happy, thinking that they have a chance, whilst you don’t have to worry about the creepy guy from the bar actually calling you. The downside is that he’s probably going to call the number, and you have no idea who’s at the other end. In this case, it’s someone who has no problem telling it like it is.

An emergency

As you get older a transition happens. Your parents stop having to care for you as much and you start having to care for them more. It’s a circle of life kind of thing! It does mean, however, that you end up spending more and more time worrying about your parents. Especially when you get messages like this.

As a grown-up daughter of a mom who would totally text me this message, I can imagine the terror that went through her daughter’s mind when she read the first line. A whole plan was formed to rescue her mom, and then she discovers that it’s essentially an IT question. Everything is fine, but she’ll probably need a glass of wine now.

Keeping up with the culture

This is what happens when parents get Facebook. While the younger generations are used to getting battered by ads, advertorials, and targeted messaging online, older social media users are often quick to jump on the next bandwagon without checking if it makes sense, or is even true.

So, aside from the randomness of this mom suddenly deciding that her adult child needs to immediately take probiotics, the child on the other side of the conversation also has to deal with what they think is a huge judgment on how cultured they are. Although, misunderstanding and judgment in one conversation sound like a pretty normal afternoon with your parents to me.