36+ Hilarious Text Conversations That Have Us in Stitches


There’s no doubt that instant messaging has changed our lives for the better. Being able to contact friends and family with the touch of a button and get a response within minutes saves so much time. But sometimes, the convenience of quick messaging backfires.

From accidentally texting your date instead of your friend to total misunderstandings, texting can create hilarious situations. These texts will have you cringing from secondhand embarrassment.

I’m a Cool Mom

It doesn’t matter how big and independent you get, your mom will always worry about you. It might be annoying as a teen, but it gets quite endearing as you get older.

Once this mom realized that her kid was safe, she started to diffuse the atmosphere by dropping quotes from everybody’s favorite teen vampire movie. The timing was perfect.

Tinder Talk

Dating apps are rough, and looking for your diamond among them isn’t easy. That’s why you have to be creative in order to stand out from the crowd on these kinds of apps.

If all else fails, you could always try bursting out into song mid-conversation and see how far that gets you with your crush. It’s definitely worth a try.

Doggone It!

While they’re often seen as better for communication, in-person conversations aren’t without their misunderstandings. Words can be misinterpreted and misheard, leading to some complicated situations. Sometimes it’s a lot easier to understand something once you’ve seen it written down.

While this person must have felt so awkward shouting death row in a dog park, we can’t help but laugh when we imagine it!

Sharing is Caring

Food plays a massive role in almost every culture. It’s a way to bond with people from different backgrounds and share experiences. But usually, the sharing of food is agreed upon first.

We can’t even imagine getting this message from our takeout delivery person, especially while on an empty stomach. Maybe next time they’ll ask for a bite before just taking one.

Backfiring Trick

It’s sometimes oddly satisfying to watch somebody mess up when they were just about to do something wrong or hurtful. It’s as though karma is waiting just around the corner to make their move.

We’re assuming that the magic trick in question was probably the disappearing act. Maybe next time they want to break up with somebody they’ll do it face to face.

Make Your Move

Back in the day, a breakup was done face to face. But today, people feel the need to hide behind computer screens, letting technology do all their dirty work.

While Adele warned us that love is a game, clearly we didn’t heed her words. What kind of way is this to break up with somebody? This sure is a bold move.

Trip Down Memory Lane

The beauty of modern-age technology is that it keeps you close to your friends and reunites you with old acquaintances you’d otherwise lose touch with. Unfortunately, not everyone with a smartphone wishes to be contacted all the time.

While we can see why it would be a little weird to receive a text like this after years of not talking, they could have reacted a little nicer than they did.

Mother’s Ruin

There’s a strange part of growing up where you realize that your mom and dad are just regular, flawed people. It happens to the best of us, and it’s a super weird feeling.

Taking care of a parent who drinks too much feels almost like role reversal, but they deserve a good time, too. Kudos to this kid for reminding their mom to stay hydrated.

In a Pickle

Mishearing somebody’s name or movie title is fairly common in face-to-face conversations. Because of accents and mispronunciations, they can happen to anyone and it’s nothing to be ashamed of.

This is the kind of verbal blunder that could probably have gone unnoticed for years as the mistake sounds very similar to the real title. Luckily it was picked up immediately. Hilarious!

Insect Crime Scene

Sometimes the wildest things happen when nobody is around to see them. That’s when texting comes in handy. You can share moments with people who aren’t even in the room with you. Just bear in mind that not all moments are worth sharing.

We’re hoping that by “mail” they meant to send a photo. But honestly, who knows at this point? Some people do the craziest things.

Unrequited Love

There’s nothing worse than having genuine feelings for someone who doesn’t feel the same way about you. It’s truly heartbreaking and difficult to get over. Sometimes getting closure is the only way to move forward.

But what do you do when there’s no closure? We want to be mad at this person for reacting to such an outburst of love in this way, but we totally get it. Pizza is life.

Non-Discriminatory Sucking

Texting somebody what you really think about them instead of saying it to their face, has never been easier. We’re seeing more and more people expressing their feelings these days through devices. It’s so impersonal!

However eager you are to get your feelings across, it’s probably best to check you have the right number before you send this kind of message.

Kiss and Make Up

Being confused with your sibling is something that anyone with brothers and sisters can relate to. Having more than one parent in common results in you sharing most of your DNA with siblings. It can be a blessing and a curse

We can imagine this person’s relief when they realized that the mentioned smoocher wasn’t his significant other but her sister. Jumping to conclusions much?

Screening Texts

When reading a text message, it’s very easy to understand things at a literal level. You cannot see the person or hear their tone of voice, so what they write in a message can be pretty open to interpretation.

We don’t know if this dad was being serious or if he was being sarcastic, but this response is absolutely hilarious.

The Croc Life

When it came to the Crocs fad that took the world by storm, you were either one of three people. The most common type of person felt that there was no level of comfort worth looking that silly for. Then there were those that knew they looked kinda weird, but loved their pair of shoes to no end.

Lastly, there were those who actually found the shoe comfortable and aesthetically pleasing. We can’t get our head around it, but each to their own!

Sandwiched In

After being under the influence, it’s not uncommon to crave something to snack on. With your head being a little cloudy, coming up with ideas on what to eat can be tricky.

With the help of iMessenger, you can share your post-recreational activities with friends in an instant. Nothing cures a case of the munchies quite like a really good sandwich.

Bad Tim-ing

While watching a movie, this girl got a text from her coworker, asking her to cover his shift. Though she was upset about the last minute request, she was about to be even more outraged.

It turns out that same coworker had just texted her boyfriend, who was sitting on the couch next to her, to ask if he wanted the other ticket to the concert he was going to tonight. Oh Tim, that wasn’t very smooth.

Beacon of Hope

Giving directions can get confusing. With all the wrong turns and one-way streets in cities, it’s much easier just to show somebody the way rather than trying to explain.

This man needed their delivery guy to know where they were, so instead of sending a live location, he got a little more creative. Batman was clearly on to something here.

Self High Five

Coming up with defensive one-liners to bat off incoming insults isn’t something everybody can do on the spot. It takes a certain level of wit and humor to churn out comebacks so quickly.

Life is tough, you’ve gotta give yourself a pat on the back wherever you can. If that means laughing at your own jokes then so be it.

Talk to the Restraining Order

Compliments can be a lovely thing to receive when they’re given in the right way by the right person. When it’s somebody you barely know or even like, it can get pretty creepy.

This girl came up with a very witty way to tell her admirer exactly what she thinks of his unwanted advances and we’re here for it.

Typo Tragedies

Typos can land you in a world of trouble if you’re not careful. The most innocent of sentences can turn into the wildest of innuendos all because of one misspelled word. Proofreading has never been more important.

We’re hoping this kid has recovered from their mom’s typo, and that their mom has recovered from her anniversary present. Nothing screams romantic quite like gifting your wife of 30 years a mop.

Dumpster Diving

Nobody knows you better than your own partner. So when this person saw how forgetful their significant other was, they made it their business to make copies of everything that they didn’t want to lose, including their wedding photo — just in case.

Two uniformed men who worked as trash collectors came to this person’s house explaining that they found a photo frame belonging to them. They had no idea that she had accidentally thrown it away. But once their partner had noticed, he made a copy and replaced it

Bad Apple

It’s difficult to stand out and get a girl’s attention over text when all you’ve got to show for yourself is your name and your profile picture. Sometimes you have to get a little creative.

If you want to get a girl’s attention, we’d recommend steering away from anything to do with bathroom habits, however impressive you think it may be.

Mother Doesn’t Always Know Best

Trends change as frequently as the weather. Once you get the hang of one trend, the kids are onto the next and you look behind times. There’s no harm in trying to keep up though.

This mom was determined to stay relevant and started learning the language of the future generation. We think she’s still got some learning to do.

Oedipus Complex

Most people have a list of criteria that their future partner must fulfill. Good personality, respectful, loyal, etc. But what ought to be up there at the top is “not having the same name as one of my parents”.

At least this girl was honest and she got it off her chest when she did. However, his nickname joke couldn’t have been more poorly timed.

Lost in Translation

It can be horrendously awkward for everyone involved when somebody approaches you in a bid for your attention and it backfires. It’s important to remain as authentic as possible when meeting new people and not to put on an act.

In this case, we’re not sure what happened, but it’s not cute and it’s giving pick me girl. However, it definitely got their attention.

Capital Idea

We all act as though dad jokes are awful and cringy when in reality they can be pretty hilarious. Instant messaging apps have given fathers a whole new platform to showcase their comedic repertoire.

This is great news for fans of this kinda humor. However, if these sorts of jokes have you dying on the inside, maybe get yourself an old Nokia to avoid the group chats.

Attention Please

Grabbing your kid’s attention is a challenge in itself. Especially as they seem to have selective hearing and will conveniently not hear you when you need their help with errands.

This smart mom was one step ahead. Knowing exactly what her kid wanted to hear, she managed to get them to open their chat to see the list of errands that were waiting for them.

About Last Night

Back in the day, if you had too much to drink, you’d wake up and have zero recollection of your antics. However, in this generation, we have it all on record. Forever.

We’d imagine that this person woke up with a blinding headache wondering what had happened the night before. They’ll probably be relieved to read back this text conversation and see that they only drank “a baby and half donzen of babies.”

Piece of Cake

When having conversations over text messages, things can get misconstrued and tones can be misinterpreted. It happens to the best of us. In some instances, a real conversation face to face is the only thing that will suffice.

That’s a pretty harsh text to receive if you believe your love to be unconditional. We hope the pieces of cake helped at least.

Transformative Experience

It’s fun to go out in the evening and have drinks with friends, but knowing your limit is key. When things start getting a little weird, it’s time to stop.

This is definitely one of those times. Talking to inanimate objects isn’t strictly a sign of madness. However, if the object replies, we recommend getting a second opinion from a doctor.

Birthday Abruptness

Thanks to social media, we no longer forget the birthdays of loved ones, friends, or even distant acquaintances. With push notifications reminding us, and the ease of apps, sending well wishes has never been easier.

Some pleasantries that we find ourselves doing in face-to-face conversations don’t always translate right over text. That’s okay, though. It’s the thought that counts.

Stalling for Time

One perk of instant text messaging is the ability to share horrendously cringy stories in real-time with friends. It also allows your friends to laugh hysterically in real-time, too.

There’s truly nothing as embarrassing as saying something weird out loud, only to realize that you’re not alone in the room. He probably waited for the cougher in the next stall to leave before coming out himself.

Road Rage

Friends are there to share the good times with you as well as the bad. They’re also always there to remind you of what you got up to when you’ve had too much to drink.

Some things are better forgotten, and this is one of those things. Asking a cop to use their in-car computer? This little stunt would blow your cover.

Helping Hand

With the help of easily available software and YouTube Photoshop tutorials, you can change aspects of your appearance with the click of a button. Just be sure that you give detailed instructions to whoever is doing the editing.

It’s super easy to take a text message literally or at least pretend to misunderstand it. This photo editor decided to follow his instructions to a T and the result was hilarious.

Scarring Experience

Comforting your significant other when they’re feeling down should go without saying. When they’re upset you should be there for them no questions asked. But what if they were the ones in the wrong?

It can’t be easy learning that you’re in a relationship with somebody who laughs when Disney characters die. We can only hope they reconciled shortly after this text convo.

Lost for Words

It’s happened to the best of us—you’ve realized something’s missing from the shopping list and your significant other has already left for the store. You text them the item at light speed, hoping they’re still there.

Sometimes it can be hard to summon the words when you’re rushing to do something. Thank goodness the person receiving the request understood exactly what was meant.

DoorDash Do’s and Dont’s

From wrong numbers to typos, there’s a plethora of mishaps that can occur when you’re using modern technology. The newest piece of tech that’s causing problems is voice dictation tools.

If you don’t enunciate every syllable and vowel correctly, you could end up saying something pretty savage and rude without even meaning it. However awkward, it makes for a hilarious story.

The Vibes are Not Immaculate

While tone isn’t something that’s always perceived correctly over a text, you usually know when your messages are being ignored. What’s important is that you stick to the boundaries that you set and remain respectful.

You’d think that in this day and age, a “handsome boy” would be able to handle rejection in a slightly more mature and respectful way. Unfortunately, some are still living in 1923 and haven’t caught up yet.

Swipe Left

When your dating life is 90% left and right thumb-swiping, coming up with inventive ways to introduce yourself to your latest match can be tricky.

As far as opening lines go, this is about as original as it gets. Sure, the person receiving the text might have been completely cringed out (as are we), but we have to give credit where it’s due— it’s creative.

Time to Make New Friends

Making friends comes naturally to a lot of people, but not everybody is lucky enough to have that level of charisma. For some, being outgoing is quite a challenge and can leave them feeling lonely.

It’s cringeworthy and we have secondhand embarrassment. We’re guessing that the recipient feels the same way as the last text wasn’t even worth responding to.

99 Problems

The concept of two males battling each other over the affection of a lady is something that’s been happening since humans lived in caves. Why lock horns when you can give each other math problems to chew over?

This math problem flew over our heads. Even still, we definitely think that it’s a far better solution than actually fighting over a girl.

Bugging Out

Sometimes we need a friend who likes to keep it simple. But is there ever such a thing as keeping it too simple?

While we don’t expect our friends to have the answers to everything insect-related, we do expect them to be at least a little helpful. We’re hoping that neither of these people are considering a career in Entomology.

Sampling the Goods

Working in the food delivery industry comes with its challenges. Taking piping hot delicious food from one place to another and none of it’s for you can really work up an appetite. The temptation is real.

Testing a customer’s food without asking is a super weird thing to do, though. We hope this delivery guy isn’t expecting a tip after that.

I Love You, Too?

Admitting to your partner that you love them is a scary moment for anyone, especially when you’re the one saying it first. There’s no telling how they’ll react and it could completely backfire.

There’s nothing like adding a little comedy to an otherwise romantic moment between a couple. We can only hope it was reciprocated after the questionably timed joke.

Kidding Around

We’ve all texted or called the wrong number. It’s awkward for a few seconds, and then you both forget about it and go on about your day. However, continuing the chat doesn’t usually happen.

Once it’s clear that the recipient is not only the wrong person, but also not interested in the purchase, it’s usually the cue to end the conversation. We can’t imagine being on the receiving end of this text!

DoorDash Dating Service

The texting generation came with many new perks. One plus is that you can order a whole meal to your home without making any contact with other human beings. Or so this person thought.

Imagine not only receiving your dinner at your front door, but also getting a whole new boyfriend. This is probably a lot more than they ordered.

Wrong Wife

Breaking up with somebody over text is a cowardly new way to end a relationship with somebody. Tough conversations like these ones should always be done in person.

Getting this sort of text from your husband is far from ideal. But to then discover it wasn’t for you? We imagine this woman was horrified, then calm, then back to horrified again.


Online dating can have its issues. The most common of them is the phenomenon of catfishing. People can get self-conscious about their appearance and maybe post an old photo of themselves or a photo of somebody else entirely.

But no matter how self-conscious you are, you still have to be honest with people. Pretending to be somebody else online is considered catfishing. It’s not only illegal but it’s a super mean thing. Turning up to a first date to be greeted by somebody you don’t recognize can really spook a person.

Flirty Banter

Have you ever been in an awkward situation where somebody is trying to have a conversation that you’d rather not be in? It can be super uncomfortable when they don’t get the hint to stop talking.

We can’t think of a better way to avoid an unwanted question. Just respond like a 17th-century peasant would and watch them run.

Grandpa Style

Grandparents are our personal connection to history. When we think of grandfathers, we think of wise old men surrounded by their grandchildren, telling stories of their times in the army and how they met your grandma.

What we don’t usually imagine is a grandpa sitting on YouTube catching up on current videos and music. We have so much respect for this man!

Tears of Laughter

Getting the hang of modern technology isn’t something that comes naturally to everyone. This can lead to some hilarious mishaps and hugely inappropriate blunders over text conversations.

While this mama’s intentions were clearly good, we can’t imagine a worse scenario to make this kind of mistake. In her defense, the happy crying emoji is very similar to the sad crying one.

Mood Killer

Imagine having it all. The looks, the personality, the charm. Then imagine that you ruin your chance with a lovely-sounding girl all because you went a little overboard with the guac references. This couldn’t have been fun to hear.

We hope that in the future this guy doesn’t lose his faith in love and finds the avocado to his toast.

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