45 Funny Text Pranks We Want to Try Immediately

This article appeared in Drivepedia and has been published here with permission.

Make Your Friends Lose Their Minds With These Hilarious Text Pranks

It’s always fun to mess with people a little bit. After all, what’s the point in walking around with a phone in your pocket if you don’t use it to cause a little chaos? It could be a cheesy joke, a pretend glitch, or the classic prank of switching the autocorrect in someone’s phone so their messages turn into nonsense. Take a page out of these pranksters’ books and try one of these funny text pranks.

Shifting the Shortcuts

This target is clearly trapped in an endless cycle of pecan pies (mm, that sounds delicious).

Shifting the Shortcuts

We guess that the upside of this prank for the target is that they’re going to get a bunch of tasty pecan pies from the store. On the other hand, they probably feel like they’re losing their mind.

The Grammar Gangster

Messing with the shortcuts on someone’s phone is a classic smartphone prank. This prank works particularly well on people that aren’t very technical. Otherwise, your target will realize what’s going on and simply switch their shortcut back.

The Grammar Gangster

However, if you pick on someone that doesn’t know the ins and outs of an iPhone, this works great. This text message prank is aimed at grammar sticklers, and plots to undo their correct language use. We would not respond well to this.

A Niche Newsletter

We’ve seen the un-cancellable cat facts, but what about Daily Llama Images? Honestly, we aren’t sure that we’d cancel either of these fake services. Maybe it would be a prank back to force your prankster to keep plying you with adorable images of llamas, or bits of trivia about kitties. Bring it on!

A Niche Newsletter

This llama prank includes a fake daily charge, which adds slightly higher stakes to the whole endeavor. It also hilariously asks its “loyal customers” to rate them from one to five.

Moth and Dad

This is a mixture of a text prank and a dad joke, and really, what could be better than that? We begin with a teenager living at home, texting their dad to get rid of a moth outside the bathroom door. They message their parent a few times, getting increasingly scared of the fluttering beast that’s torturing them.

Moth and Dad

Eventually, their dad responds, but in the guise of their worst nightmare — the moth. The moth warns that they will be next.

An Awful Autocorrect

Are text message pranks, in and of themselves, juvenile? Yes, they probably are. Are pranks, in and of themselves, childish? Yes, they probably are. And is this text message prank — where someone autocorrects the word “cool” to the word “farts” — immature? Well, yes it is. But, that doesn’t make it any less funny.

An Awful Autocorrect

The word “farts” is simply very funny, both because of how it sounds and because of what it refers to. Forcing someone to type “farts” is even funnier. Hey, we don’t make the rules.

The Old Classics

The “updog joke” has been around for decades at this point. It involves using the word “updog” and then when someone asks what that is — “What’s updog?” — you respond with a, “Not much, you?” The person could say “Does this smell like updog to you?” Or, “Have you added me on Updog?” Regardless, they want you to ask, “What’s updog?” Get it?

The Old Classics

In the second season of The Office, Jim uses this joke on Michael. Of course, the blundering boss absolutely loves it, and runs off to find his own target.

What’s This All A-Bot?

OK, so here’s a classic bot prank, where you text someone pretending to be an automated message. These work pretty well, especially because it’s easy to replicate the type of messages sent out by big corporations. In this example, someone is posing as ice-cream brand Baskin Robbins, but on closer inspection, it’s a pretty dodgy deal.

What’s This All A-Bot?

Really, who wants hourly text messages from anyone, never mind an ice-cream proprietor? Of course, with these pranks, responding “STOP” rarely has the desired effect.

Rick Rolling All Day Long

For anyone that has miraculously managed to escape the internet phenomena of rick-rolling, you’re about to find out what it’s all about. Basically, for over ten years now, chuckleheads on the internet have been springing the 1987 Rick Astley hit “Never Gonna Give You Up” on unsuspecting internet browsers.

Rick Rolling All Day Long

For example, you may click a link for something interesting and instead be faced with the jolly ’80s tones of Mr. Rick Astley. In this text message version, the phrase comes up every time someone types, “Hi.”

Slime Man, I’m Home

Did you know that you can create a signature for text messages on the iPhone? And did you know that you can make it something quite ridiculous and mess with someone in a hilarious way? As we can see in this example, somebody has switched their mom’s text signature to “slime man.”

Slime Man, I’m Home

We have to confess that this makes us laugh every time. It’s just an absurd thing to choose. Would there be a scenario where the words “slime man” wouldn’t be funny?

Going All Adele

There are several categories of text message prank. There’s the autocorrect and shortcut pranks, there are the glitch and bot pranks, and then there are the song lyric pranks. Basically, for this type of prank, all you have to do is insistently and sincerely send someone the lyrics from a famous song.

Going All Adele

This example uses “Hello” by Adele, which works well because its opening line seems fairly normal. Of course, it only escalates from there — “Hello from the other sideeeeeee.”

The Weapons Manufacturer

OK, this is a different category of text prank altogether. This one comes from professional text prankster Matt Andrews, who ended up compiling his pranks in a book called Textastrophe: A Collection of Hilariously Catastrophic Text Pranks. What we’re saying is, this guy knows what he’s doing.

The Weapons Manufacturer

Andrews responds to Craigslist ads with ridiculous responses. In this example, someone was looking for pepper spray, and instead was offered a hairspray flame thrower. Needless to say, they weren’t thrilled.

Where’s the Cream Filling?

Here we have another shortcut prankster, this time making their mom say “Twinkies” every time they want to say “lol.” We can’t help but feel just a little bit sorry for these moms. After all, they’re just going about their business, albeit with slightly less technological knowledge than their children.

Where’s the Cream Filling?

All they want to do is use some modern internet slang, and instead, they get hit with a Twinkie-based joke. Also, it’s adorable that this mom tells her kid to “try it.”

Reality TV Realness

Of course, when messing with someone’s shortcuts, you don’t just have to switch one word for another. You could also insert long passages of text, or strange little bits from weird reality shows that you watch. In this case, someone’s mom is trying to tell them that they’re divorcing their father (over text message, really?), and instead spouts the opening from Pawn Stars.

Reality TV Realness

In this example, perhaps it’s more obvious that this is a prank. It’s one thing to keep saying pecan pie, or Twinkies, but this?

A Prank Too Far?

OK, so now we’re getting into slightly more dangerous territory. So far, we’ve only seen text message pranks that irritate or amuse people, but this one has the potential to really mess with someone’s emotions. Warning! Text message pranks can have actual consequences, so just keep that in mind.

A Prank Too Far?

Here, the prank is to tell someone that you made out with their boyfriend. Is this a prank, or is this just a cruel thing to do? You decide.

Sometimes It’s the Simple Things

To return to a more innocent world, this shortcut prank basically switches the word “no” to the word “Moo.” OK, we’ll admit, this isn’t exactly revolutionary. But, if you’d rather poke fun than cause someone to have an emotional breakdown, this is the direction to go in.

Sometimes It’s the Simple Things

To be fair, “Moo” is so similar to “No” that this could be particularly annoying. Plus, we can’t discount the mundane embarrassment of randomly saying “Moo” to people.

Faking Your Own Death

So, this text message prank is like that episode of Friends where Ross decides to fake his own death to see who would show up at his funeral. Thankfully, this one doesn’t go quite as far, but it does involve make-believe death, and that’s something.

Faking Your Own Death

Here, Dave’s friend sends him a message, and Dave replies pretending to be his own grieving mother. His friend must have had the shock of his life, plus the made-up responsibility of informing everyone else.

Love Me, Feed Me

So, this text message prank is a bit like the song lyrics one, except it relies on people knowing (or not knowing) popular culture. For these types of pranks, you start off as if you’re being serious, but then add more details that reveal that you’re actually joking.

Love Me, Feed Me

In this example, someone starts off by inquiring about a missing cat, before describing Garfield, one of the most famous fictional cats in the world.

The Meanest Prank of All

We think it’s safe to say that this prank is the meanest one on this list. It’s also probably not one that anyone else can replicate, unless they also dated somebody that ended up with amnesia. Is this the plot of a teen drama?

The Meanest Prank of All

The prank itself is messaging someone the words, “I haven’t been fully honest with you.” Obviously, this sends the person into a spiral of paranoid anxiety. We’re going to say that it’s probably best not to go down this route.

Nyoom Nyoom Nyoom Nyoom Nyoom

Now, this person has taken the shortcut prank to a higher level, by replacing all of the words they could think of in someone’s phone. In doing so, they’ve basically removed their target’s ability to speak and be understood, which is pretty amusing.

Nyoom Nyoom Nyoom Nyoom Nyoom

More amusing is that they’ve chosen to replace every word with the nonsense word, “nyoom.” But, is any word on the internet really a nonsense word? Nope. In online circles, “nyoom” is the word used to describe something moving really quickly.

Go Get ‘Em

Here’s a good text message prank, this time taking advantage of someone’s dodgy memory from the night before. In this exchange, someone has switched their number in their buddy’s phone to “Coach Bombay,” and then continued to persuade them that they did actually meet Emilio Estevez.

Go Get ‘Em

Of course, Emilio Estevez played Gordon Bombay in the 1992 movie The Mighty Ducks, and he’s lived in our hearts ever since. Did you know Estevez is reprising his role for a 2020 reboot of the franchise on Disney+? You’re welcome.

The Proper Prank

So, this text message prank actually takes things further than the others on this list. While the autocorrect pranks do mess with the settings on someone’s phone, they don’t force it to actually shut down. That’s what happens when someone sends this piece of code to an iPhone — it literally turns off and then restarts again. How annoying!

The Proper Prank

Apparently, this was caused by a glitch in a version of iOS, and works on a range of iPhone models.

Get the Party Started

This text message prank uses the autocorrect method, but with a more specific purpose. You see, this enterprising young person changed the word “no” in both of his parents’ phones, to rather party-centric “yes” phrases. This means that when this little dude asked if he can have a party, he knew exactly what his parents were going to say.

Get the Party Started

In order to get past this, all these parents need to do was say “nope” or “nah” or “never,” but instead they just get mad.

I Am Your Father

It was only a matter of time before this text message prank came up. Is there ever a type of joke that doesn’t include some reference to Star Wars? It’s just too iconic a franchise to ever slip out of pop culture references. And this is especially true when it comes to Darth Vader and his famous line, “I am your father.”

I Am Your Father

The prank itself is just changing all of someone’s contacts to Star Wars characters, though we’re impressed with the prankster’s eye for detail.

Un-Cancellable Cat Facts

Sending someone cat facts is a type of bot prank, where you pretend that your target has signed up to a daily texting service. You start off by thanking the person for signing up, and then escalate the service as days go by.

Un-Cancellable Cat Facts

Of course, you give your target opportunities to “cancel” the service, but that never quite seems to work. Weird, right? This prankster is particularly good at imitating a bot. We can imagine their target getting more and more irritated with each text.

Just Plain Ridiculous

Here’s a texting prank that originated with a Craigslist advert. Warning to all Craigslist posters — putting your phone number online may lead to some less than sincere responses. The original poster here is in need of a band and is asking the so-called band what genre of music they play.

Just Plain Ridiculous

The prankster starts out by evading their question, and making their band sound somewhat mysterious. They then come out with a clearly absurd genre, and a stilted joke about “old people.” Lol.

The Ole Pregnancy Prank

We’re back to the high stakes prank zone, where text message pranksters really mess with their friends and families, and risk causing actual emotional distress. Seriously, guys — please think these through before doing them, because some people will just not respond well. Seriously!

The Ole Pregnancy Prank

This prankster has used the time old “I’m pregnant” gag, but via text message instead of in person. This prank works better via text, because you don’t have to keep a straight face while delivering “the news.”

Fleeing the Refrigerator

Here we have another example of a prank that has survived across time and technology. Back in the days of yore, before caller ID alerted us to who was calling, kids would call establishments and ask, “Is your refrigerator running?” The respondent would say “yes,” and the kid would triumphantly say, “Then you better go catch it!” Cue hysterical laughter.

Fleeing the Refrigerator

The text message version allows for more creativity, like suggesting the refrigerator is a vengeful and sentient creature.

Pranks Versus Reality

Now, it’s debatable whether this is actually a prank, wishful thinking, or just outright lying. But for the recipient of this text, there was a moment where they must have been either jealous or pleased for their friend. That’s sort of a prank, right? We feel like forcing fake emotion is in the prank-zone, so we’re counting it.

Pranks Versus Reality

Perhaps this “prankster” is just delusional, or living in their very own fantasy land. Regardless, we’re pleased that they at least have mac and cheese.

Quit it Already

Teehee — admittedly, this prank is right up our street, because we do love a bit of language-based humor. Obviously, it would be extremely annoying to attempt to tell your friend why you’re unhappy, and have them only respond with very literal answers. But also, ha-ha, good one.

Quit it Already

Unlike some of the more mindless text message pranks on this list, this one is almost cerebral — almost. Also, you can’t argue with these accurate responses. Lava just isn’t cool!

Wrong Number, Sorry

This text message prank is as basic as they come, but it’s also pretty funny. In order to pull this one off, all you have to do is respond, “Who’s this?” to whoever texts you. Imagine how infuriating that would be, especially if you know that they have your number.

Wrong Number, Sorry

To escalate the prank further, you simply continue to pretend that you don’t have their number. If this works as planned, the other person will start to doubt themselves.

Help a Friend Out

OK, so we haven’t come across any of these text message pranks yet, but we have to say, we’re a fan. Admittedly, we aren’t the biggest supporters of adding anxiety to someone’s life for a joke. However, we’re more in favor of someone thinking their friend is a murderer than someone thinking that their teenage partner is pregnant. Maybe that’s just us.

Help a Friend Out

This prank involves asking your friend for advice on how to hide a body they “found” in their house. And that’s it.

The Big Let Down

This is a cruel one, but it’s pretty low stakes, so have at it. In order to pull off this nasty little prank, you just text somebody that they were right all along, and ask them how much you owe them. This shady trick will cause the person to think of all the possible things they could be right about.

The Big Let Down

They’ll also start wondering how much money is coming their way, and start to create reasons why they must be owed it.

It Must Be a Glitch

When you mess with somebody’s phone, a good way to distance yourself from it is by suggesting that they have a glitch. Your phone keeps autocorrecting to, “farts?” Weird, must be a glitch. You keep getting facts about cats? Strange, it’s probably a glitch. All of your contacts have been renamed as Star Wars characters? Ah, typical glitch.

It Must Be a Glitch

This prankster is obviously relentlessly texting the word “diapers” to his friend, and then pretending that they have no idea what’s happening.

We Have Eyes on You

To be completely honest, this is our favorite text message prank on the entire list. It just makes us laugh every time we read it. To do this prank, you text one of your friends and ask them where they are, and what they’re up to. Normal enough, right?

We Have Eyes on You

Then, when they reply with the information, you text them back but pretend that you’re texting someone else about them. This will make them think that you’re spying on them, which will make them rather unsettled. HA!

I’ll Be There for You

Here’s another prank that relies on information from a fictional universe. These pranks only really work if the person you’re pranking doesn’t get pop culture references. That way, you can really dig into the ridiculously obvious details of a TV show or movie without your target knowing that you’re talking nonsense.

I’ll Be There for You

This prankster named Ross is taking on the identity of Ross from Friends — paleontology degree and everything. Their friend must have never watched an episode of the sitcom in their life.

The Horrible House-Sitter

So, this is a text message prank that you use when you’re housesitting for somebody. However, if you do this prank, then you will not be asked to housesit again. Although, it is possible that the homeowners would be so pleased that their house is still in one piece, that they’d hire you again in the future.

The Horrible House-Sitter

For this prank, you simply act as though there are a series of terrible emergencies in the home you’re in charge of caring for.

A Total Hoot

There’s a Venn diagram of bad jokes and text message pranks, and this one sits right in the middle. In order for this text prank to work, you need your target to respond with, “What? Who?” And, to be honest, do owls really make a noise that sounds like “What, Who?” We aren’t so sure!

A Total Hoot

We reckon this joke needs to be rewritten a little — or rejigged to sound more like an owl. Maybe something to do with Twix, and shoes? “A Twix, a shoe.” …Maybe not.

A Very Easy Bet

This is another pretty juvenile prank, but one that we can really get behind. What can we say? It made us smile. However, this person seems to be a pretty easy target, as they were duped into losing this so-called bet very quickly.

A Very Easy Bet

As we can see, the prankster messages somebody betting them that they can make them say “red.” With just a little bit of deflection and some reverse psychology, they’ve proved their point in no time.

You’re Absolutely Pun-Believable

This can be considered a text message prank if text message pranks are just sending someone a list of thematically connected puns. We’ll be honest — we love it.

You’re Absolutely Pun-Believable

This prank starts off with somebody texting their pal with a pretty bad joke. When their friend isn’t very enthusiastic, they add a pun that builds on the joke. When that doesn’t work, they do it again. We’d argue that this friend has no sense of humor.

The Lyrics Game

This particular text message prank is a combination of the lyrics prank, and the fictional universe prank. For those of you that don’t recognize it, these are the lyrics to the fabulous and iconic ballad, “Part of Your World,” from the fabulous and iconic Disney movie, The Little Mermaid.

The Lyrics Game

However, when presented line by line in text message format, this song looks like a series of very strange questions. Top tip — if you ever get a series of messages like this, go ahead and google it.

Like a Good Neighbor

State Farm is a large group of insurance companies that operates across the US. So, what better text message prank to pull on one of your friends than to change every contact in their phone to State Farm? Wouldn’t that be annoying? Or, wouldn’t it be hilarious?

Like a Good Neighbor

It would be funnier still if the target of the prank then messaged their contacts in order to get their actual name, and their contacts played along with the original prank.

That’ll Do It

OK, we’re back to the high stakes pranks, where a text message can elicit a seriously passionate response. So, this prank is used when your girlfriend or boyfriend keeps texting you and you want them to stop. Or perhaps you want them to explode, which is basically what happened here.

That’ll Do It

So, if your other half is bothering you with messages, you simply respond with “He’s busy” (or she). Of course, this implies that your partner is with someone else. Hmm.

Just a Touch of Joyce

This person has taken the shortcut prank to extreme levels, by replacing the word “dirty laundry” with large passages from James Joyce’s novel Ulysses. For those that don’t know, Ulysses is an extremely long and dense modernist novel that was first serialized in 1918.

Just a Touch of Joyce

This texting prank made headlines, and The Huffington Post called it “the greatest auto-correct prank we’ve ever seen.” Again, just a little bit of us feels bad for the mom in question — she’s just offering to wash his dirty socks.

A Rather Misguided Attempt

Here’s another prank that we aren’t completely convinced is a prank. It seems a little bit more like coercing someone into saying something they don’t mean to. But also, didn’t they notice what they were sending before they sent it? What’s going on here?

A Rather Misguided Attempt

Basically, this “prank” involves asking somebody a series of questions so that they will respond with a sentence that you want to hear. In this case, it’s “Will you go out with me?” in a rather roundabout way.

Doubling Down on Dodgy Jokes

And last but not least, we have another combination of old jokes and a text message prank. This text uses the age-old, “Why did the chicken cross the road?” joke — and the “knock-knock” joke.

Doubling Down on Dodgy Jokes

Did you know that the knock-knock joke appeared as far back as 1606, with Shakespeare himself using the words, “Knock, knock! Who’s there” in Macbeth? And, the first chicken crossed the road in an 1847 edition of The Knickerbocker. Sometimes, the old ones are the best ones, eh?

30+ Texts People Have Received From Their Coworkers That Are Slightly Strange and Even Concerning

Sometimes, you forge great bonds with your coworkers! Other times, the situation isn’t quite as fun. When it came to texting with coworkers and bosses, these people all had some strange, odd, and even outright upsetting exchanges that left them concerned.

Is it Worth It?

Running late is stressful and it’s a situation that most people want to avoid. Still, it happens to everyone from time to time and that’s understandable. We’re glad to see that this boss wasn’t too upset that their employee was running behind. Yet, they still had a condition for their tardiness.

Is it Worth It?

Check the Group Chat

As we just said, if you’re going to complain, it’s best to know your audience. This includes when the complaints are in bigger groups, like a group chat.

Check the Group Chat

The last thing you want is to think you’re venting to your coworkers to find out that your boss is in the chat. Not to mention, it seems risky as far as employment goes to start calling names with a direct manager. Kelly wanted them to know their mistake immediately too.

Say That Again?

When it comes to coworkers, there are some questions that are fine to ask. Finding someone to cover a shift is often the bulk of coworkers’ conversations.

Say That Again?

On the other hand, there are questions you should stay far away from. Namely, you shouldn’t ask them what type of underwear that they wear. We’re glad to hear that this was a mistake rather than a genuine question and it seems like they moved on just fine.

That’s One Way

It’s everyone’s nightmare — taking a screenshot of a conversation and sending it right back to the person. After all, that’s a much different situation than asking a friend for advice.

That’s One Way

In this case, the mistake made the situation much simpler in addition to making it much more awkward. Danny didn’t wait long to let them know exactly what kind of mistake that they made. They weren’t going to hear any explanation for it either, this person was free to simply never come back.

An Honest Opinion

Sending a message to the wrong person can have some catastrophic results. Luckily, this person didn’t send anything too weird — just a simple selfie.

An Honest Opinion

On the other hand, it seems like their boss was more than a little irked by the message. Either that or they have a vendetta against the concept of selfies. No matter what the reason was, they definitely didn’t just let this person off the hook for the mistake.

A Little Typo

When you’re conducting a professional conversation, you have to be careful what you say. After all, some things are considered impolite in some circles.

A Little Typo

For instance, you probably shouldn’t tell your boss or coworkers that you’re stuck on the toilet. Luckily, this one was just the fault of autocorrect and not the result of someone actually telling their employer about their bowel movements. It seems like they took the mistake in stride, though!

They Just Want to Fit In

Once in a while, your boss has a question that you and your coworkers simply weren’t expecting. There’s nothing necessarily wrong with it, the question just happened to catch everyone off-guard.

They Just Want to Fit In

This text is a great example of that. This person just wants to shake up their style a bit but doesn’t know where to start. What they do know is that they like the “cool goth clothes” that the people they work with also happen to love.

“Not Normal”

There are a few things to avoid when you’re trying to become friends with your coworkers. However, this can also mean that trying to make friends can be harder than it seems.

“Not Normal”

We can only assume this person was trying to inject a little bit of personality into the conversation. The actual result was a little more uncomfortable than that, however. It probably didn’t help to keep messaging them after this coworker was clearly uninterested.

Just Asking

There are plenty of people who wouldn’t want their coworkers to ask them out. They definitely wouldn’t want this situation to arise in a pushy way.

Just Asking

Unfortunately, that’s exactly what this person’s coworker sent them. It starts off innocent enough but they jump the gun right into their question without any preface at all. In addition, we have to say that this message is made all the more strange by the push to “please say yes” right away.

Bored of Being Bored

Everybody complains about work from time to time. The key is to complain to the right people. After all, not everyone is the right person to talk to about it.

Bored of Being Bored

As an example, you might not want to text your boss about how little you’re enjoying being at work. While they probably already know, since it’s work, but it’s not quite polite to tell them that in most situations. We can only imagine that this was a text to the wrong number.

Probably Not the Right Number

Some of the weirdest texts you can get are the ones not meant for you. It can seem especially funny if the text you got seems like it’s from the middle of a conversation.

Probably Not the Right Number

This coworker was probably more than a little confused to get such an odd picture of the person they’re used to working with. The fact that it’s a part of a different conversation almost raises more questions than it answers. It’s good to see that they could both laugh about it.

A Little Bit of Poetry

This conversation already started in a weird place with this coworker talking about their own looks. A general encouraging message was a fairly neutral way to go. Unfortunately, the conversation only continued to derail from there.

A Little Bit of Poetry

Generally, messages with this sentiment from coworkers can come off strange and pretty uncomfortable. Adding a poem about how beautiful their coworker’s smile was and talking themselves up again definitely pushed this into a weird and concerning territory.

Not Meant for the Boss

There are some people you have to maintain a professional relationship with. This usually doesn’t include telling your boss that you fall in love with them every time you text.

Not Meant for the Boss

It’s pretty clear that this person didn’t intend to confess their love to their boss. On the contrary, that was meant for someone else entirely. We have to respect how ready to roll past the issue they were and wonder if their boss gave them that shift off after that.

A Straightforward Answer

There are times that you really don’t want to hear from your boss and coworkers. Namely, you probably want them to leave you alone on your day off.

A Straightforward Answer

Their boss even tried to entice them with the promise of a monetary bonus for the extra work. Still, they weren’t tempted but they chose a strange way to convey the message. It seems like these two have a joking relationship but we surely wouldn’t expect this off-the-wall response from someone on why they can’t make a shift.

At Least They’re Honest

We all have to tell our bosses or coworkers something we don’t want to at some point. For instance, you might be embarrassed to let them know that you broke the toilet.

At Least They’re Honest

At first, this person was trying to cover their tracks. It took very little time for them to decide to change tactics, though. They came clean with the truth with probably a little bit more detail on the situation than the person they’re talking to might have hoped for.

They’re Straightforward

There are a lot of jobs out there that expect you to dedicate your whole life to them. So, it can be nice when a boss takes your personal life into account.

They’re Straightforward

In this case, they were thoughtful, even if it was in a particularly blunt fashion. However, we suppose it’s a good qualifier to make sure that your employee is of sound mind before asking them to commit to an extra day of work later on.

Double-Check the Coffee

It’s not uncommon for someone in the office to do a coffee run for themselves and a few coworkers. Asking someone to grab them coffee isn’t too out of the ordinary.

Double-Check the Coffee

Conversely, we might start to get annoyed with the messages that this coworker was sending. Asking in the first place wasn’t too bad but reminding them and making sure their up might be a little overboard. We wonder why they didn’t just grab a coffee on the way so they didn’t have to wait.

Definitely the Wrong Person

We’ve already seen that texting the wrong person can be a pain. This is especially true if you accidentally complain about your boss to them.

Definitely the Wrong Person

This person was just trying to have a little vent between coworkers. Instead, they ended up being a little too blunt with their boss directly. We can appreciate that they tried to save the day with a more cordial message but it’s hard to make the first one seem professional.

How Flattering?

At this point, the idea of two text conversations with a coworker and a significant other side-by-side seems nerve-wracking. It seems so easy to make a mistake!

How Flattering?

That’s exactly what this person did when they sent a coworker a rather steamy message. We’re not sure what we’d think upon seeing this message but the coworker seemed to take it in stride, even before finding out that it wasn’t originally meant for them.

Maybe Think it Through

When texting a coworker or anyone really, it’s best to try and gauge the conversation before broaching certain topics. This person failed to do that.

Maybe Think it Through

There was nothing in this very brief conversation up to this point that gave any indication that this response was appropriate. Apologizing for missing messages from coworkers isn’t exactly an invitation for them to propose making out. There are some “knee jerk” reactions that you should just keep to yourself rather than making your coworkers uncomfortable.

Turning Off the Phone

It’s not completely out of the ordinary for someone to have a phone dedicated to work. It can create a great separation between work and personal life.

Turning Off the Phone

This also gives you the chance to — quite literally — turn your work off at the end of the day. That is unless you listen to this boss’ fairly poor advice. At the end of the day, why should this person have to work outside of the hours that they’re paid?

This Could Make Things Weird

There are a lot of messages that you might accidentally send your boss that could make things awkward or weird. At the very least, this one was wholesome in the end.

This Could Make Things Weird

Of all of the pictures that you could accidentally send your boss, a wholesome picture of a cat with a cute message isn’t the worse. Then again, it probably doesn’t completely fall into the realm of professional etiquette either.

Couldn’t Save It

As we’ve seen, again and again, there are some messages you really don’t want your boss to see. Admitting that you’re lying is one of them.

Couldn’t Save It

This person would have probably have gotten away with their fake sick day if they checked the chat before sending this message. We can’t blame them for trying to save it but, in the end, it doesn’t seem like it worked quite as much as they hoped.

Crossing a Line

There are some things that you should never say to someone that you work with. These messages are so wildly concerning and the content is disgusting.

Crossing a Line

Just the first message in this series would have been bad enough. It’s even worse that they kept going and asking. When they didn’t receive a response, they tried to play it off. We have to say, even if someone had stolen their phone, it’s a lot to expect for someone to just brush off such creepy messages.

Laying in Wait

Sometimes, you don’t make a situation with your boss awkward on accident. Once in a while, you might find it just a little too satisfying to give them a taste of their own medicine.

Laying in Wait

While it might not seem like this boss would take this sort of comment on the chin, it must have been satisfying to just turn the conversation around like this. To be fair, they were asking for the same consideration from their employee that they weren’t originally willing to give either.

Not What They Meant

Ideally, autocorrect is there to help the person that’s typing out a message. It’s supposed to correct any spelling errors that we make so that the end message is clear and accurate.

Not What They Meant

Unfortunately, that’s not quite how things turned out. Over the years, people have fought with autocorrect just as often as it helped them remember how to spell things. In this case, the word that autocorrect assumed they were trying to use in the phrase “sick day” wasn’t exactly something to send to an employee.

Unreasonable Demands

Once in a while, it makes sense that coworkers or a boss will need to contact you outside of work. On the other hand, there are certain hours that it’s impolite to contact someone.

Unreasonable Demands

It’s particularly unacceptable to ask someone to jump out of bed in the middle of the night to complete a task for them. Not only is it an unreasonable demand, but it’s also a pretty clear display that this boss doesn’t respect this employee’s personal time.

Wrong Face!

Once in a while, the awkward part of a text is easy enough to overlook. The good news is that this person could have made much worse mistakes in texting this person.

Wrong Face!

On the other hand, this person probably didn’t want to basically wink at their boss over text. Luckily, it was an easy thing to save and an easy mistake to understand someone making. In the end, their boss just laughed it off and moved on.

How Kind…

No matter if you’re with your boss, coworkers, or anyone else, you should respect their things. After all, those are theirs — not yours — at the end of the day.

How Kind…

Getting a message like this from any one of your coworkers would be upsetting. Even if you’re close, this isn’t exactly what you hope to hear about the chair you’re spending the rest of your afternoon in. We’re sure that this message wasn’t well-received.

What Did You Say?

There are certain ways that you can address your boss and coworkers. Usually, you can call them by their first name. Pet names, though, aren’t quite as common.

What Did You Say?

You probably especially shouldn’t text your boss or coworkers calling them “baby.” The end result was positive, though, with both parties laughing about the incident. However, you probably would pause to think about how much this person seemingly loved their job.

Nice Flex

Believe it or not, this person started out their conversation with their coworker with an image of a receipt showing the amount in their bank account.

Nice Flex

Security issues aside, this is an obvious flex — albeit a weird choice for it. Their coworker was quick to call them out on this too. While it still would have been cringe-inducing, we might have gotten closer to believing this was a mistake if he didn’t use it as a chance to ask them out.

Say That One More Time

When you’re conducting professional business, it’s best to be clear and concise. It’s a good idea to write a message and read it over before hitting send.

Say That One More Time

You might not want to text your boss when you aren’t fully awake either. Otherwise, you might send out something as strange and nearly indecipherable as this message to your boss. Aside from the weird wording and the unnecessary, long space, this would confuse any recipient.

A Little Jealousy

This one isn’t quite as weird as it is surprising. The only downside is that the surprise is almost immediately followed by disappointment.If you’re promised days off, it’s usually a good thing.

A Little Jealousy

After all, we all need a break from time to time. While this isn’t necessarily this person’s coworker, they were definitely trying to reach their coworker. Instead, this exchange just left the recipient disappointed that they still had to work.

Don’t Answer the Boss

There are certain questions you just don’t want to hear from your boss. It’s sometimes better to just keep conversations with people strictly to work or professional content.

Don’t Answer the Boss

As such, there are certain questions that you just aren’t prepared for and don’t know how to answer. There are a few questions we’d expect less from a boss than wanting to know what twerking means. Honestly, we have to wonder what led them to ask an employee over anyone else.

Who Are You Talking To?

As we’ve said before, there are certain things that you just shouldn’t call your boss. It’s unprofessional and, in most cases, fairly uncomfortable in the end.

Who Are You Talking To?

Still, there’s a risk that when you have two people in your phone with the same name, you might get things messed up. This person was only trying to ask their wife what they were doing tonight. The only problem was that the Melissa they were talking to and called “wife” was actually their boss.

Not an Unwelcome Mistake

There are times that a coworker texts you something weird and it isn’t necessarily uncomfortable. In fact, you might even get a few gems through a wrong number.

Not an Unwelcome Mistake

This person probably wasn’t too offended when their boss accidentally sent them this odd picture of a cat. Honestly, we’d want to know more about the cat. Is this their boss’ cat? If so, do they normally sit up like this? All in all, a cute cat is one of the best things to come of a wrong number text.

Timehop Fail

When it comes to sending a wrong number text, you already don’t want it to be your coworker. You probably especially don’t want it to be a message like this.

Timehop Fail

It seems pretty clear that this person was trying to impress someone they were seeing romantically, not professionally. While it definitely could have been much worse, it’s not ideal to send a shirtless picture to your coworker. It makes the conversation almost immediately weird.

More Questions Than Answers

No one likes getting called in on their day off. So, if your boss demands your presence, you might want to hear a pretty good explanation for the emergency.

More Questions Than Answers

To be fair, this definitely sounds like an emergency that needs immediate attention. Then again, their boss could have spared them some of the details in letting them know that their coworker had a medical emergency. Sometimes, sharing less information is better.

Autocorrect, Please Stop

As we’ve seen more than once, autocorrect isn’t always as useful as we typically hope it will be. Oftentimes, it does more harm than good.

Autocorrect, Please Stop

This message exchange is another example of this but the bad news is that it doesn’t seem like this person’s boss was as understanding as we’ve seen some act so far. This person desperately tried to fix the mistake, only to be met with a demand to call them as soon as possible which would make anyone nervous.

Forging a Closer Bond

It’s never a bad idea to stay on your coworkers’ good sides in many cases. After all, you have to spend a lot of time working side-by-side with them.

Forging a Closer Bond

However, sending “I love you” to a coworker might go too far from time to time. The good news was that this coworker was unperturbed. In fact, the two found that it was a great chance to use this misunderstanding to actually strengthen their bond as well.

Too Much Honesty

There are certain things you might say when you’re stressed to your friend that you wouldn’t say to your boss. Most people try to keep their relationships with their boss more formal than that.

Too Much Honesty

This person was aiming to keep things a little more formal until they accidentally clicked the wrong chat to send this note in. It didn’t take long for them to realize that they’d made a mistake and to try and mitigate the damage.

Do You Know What it Means?

There’s nothing more awkward than having to turn down a persistent coworker or boss. Particularly, it’s difficult when they can’t take “no” for an answer.

Do You Know What it Means?

This conversation went on before this screenshot started too. The person who is responding to the request continuously tells them that they’re out of the office and even go as far as offering an alternative. Yet, they just couldn’t leave them alone and accept their answer.

Checking In

Offering to grab a coworker coffee while you’re out grabbing someone for yourself is a nice gesture. You’d hope that someone would respond to that kindness reasonably.

Checking In

We’re not quite sure that this response doesn’t quite fall into the category of reasonable. If their coworker asked in the first place, you’d think that they’d look at their response when they had the chance. Demanding the same thing over and over again doesn’t help anything.

What an Awful Idea

There are some things that you should just never do. Included in that, there are certain things that you probably shouldn’t send your boss.

What an Awful Idea

As an example, if you want to take a day off or come in late, you usually have to give your boss a reasonable excuse. While there are plenty of situations that qualify, it usually doesn’t work to lead with a picture of yourself at a party and the warning that you might be late tomorrow.

It Keeps Getting Worse

No one should text their coworkers something like this. It’s made all the worse by the fact that the recipient clearly didn’t find this funny or endearing. As if it couldn’t get any worse, the excuse might be the worst one there is.

It Keeps Getting Worse

If they’re telling the truth, a groomsman for their wedding was playing a really inappropriate joke. If it’s a lie, like it sounds like it could be, then this person acting like this is disgusting in and of itself.