Digital Delights: Exploring The Web’s Funny, Weird, And Random Conversations

By Amy M January 1, 2024

This article was originally published on funniesnow

Today, people are glued to their phones and mainly communicate via text messages. There’s a chance that you’ve heard a lot of Baby Boomers complain about this and say they miss the good old days when people would communicate face-to-face. Sure, it’s nice to have a convo in person, but without technology and messaging apps, the world would be a far less entertaining place- we would have never gotten to see and enjoy this hilarious collection of screenshots that were shared on a Facebook group “Screenshots of messages that probably shouldn’t have been posted” – all hail technology! Today, you’ll get to see a DM someone got from a “bear,” someone’s delivery driver letting them know they ate their food, and many more rib-tickling, random messages. Get ready to laugh out loud.

Message Request from Man Eating Bear

Has anyone ever slid into your DMs? How about a “man-eating bear”? No? Well, if this person had a nickel for every time a bear messaged them, they would only have one, which isn’t a lot, but it’s still weird that it happened even once.

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We’re wondering if they went into the woods. The bear seems friendly – we would’ve gone. All jokes aside, we have to say that we would take getting this message over some creepy person hitting on us on Insta any day. This is hysterical.

No Cheese, No Friends

If you are lactose intolerant, then sorry, pal, you can’t hang out with this person. They have something against people with trouble digesting dairy. It’s hard enough not to be able to enjoy cheese without having to deal with the consequences later, but now people are getting rejected over messages because of it. That ain’t right.

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Pfft, we wonder if this person planned on getting ice cream with them but remembered that they are lactose intolerant, so they canceled their plans. They boldly assume that the person wouldn’t have eaten it if that’s the case. As they say, no one loves dairy more than someone who can’t tolerate it.

Food Thief

Beware of a food delivery driver named Adam – he eats your food and then taunts you with a message telling you how yummy it is. Maybe he did that because he was tipped poorly or just hungry, but who knows?

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We know it’s terrible that the driver ate his meal, but what we are really mad about is that he missed the opportunity to say, “Ba da ba ba ba! I’m lovin’ the burger!” Get it, ‘cause it’s a McDonald’s burger? We’re hysterical.

I’m Batman

This delivery driver is “Da da da da da da da da! Batman!” We wonder if they can get the food to a person’s house so quickly because they drive the Batmobile. That would be cool. Anyway, this is the kind of person you want delivering your food, not the other guy who eats what you ordered. 

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What would be funnier than this text message is if they actually showed up at the customer’s door dressed as the caped crusader – after all, they did say they’re Gotham’s finest. They’d deserve a huge tip if they did.

Red Flag Alert

Here we have someone on a dating app who doesn’t have, as the kids say on TikTok, “Rizz.” For the folks at home who don’t know what that means, it’s short for charisma. He clearly can’t charm or attract anyone through a message. After reading this, it also seems like he has anger issues.

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This message is funny because he completely overreacted. If he ever wants to find a girlfriend, he must devise better pickup lines and not go on a rant after someone turns him down. On a scale from one to ten, we’re sure this girl would definitely rate him a one after he sent her this message.

No Astrologers Allowed

If you are a parent and your kid ever texts you asking when they’re born, just know they are chatting to someone who wants that info to determine their astrology chart. Astrologer Chris Flisher once said, “Astrology is one of the oldest and most accurate tools known to mankind.” We think this mom would strongly disagree.

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This lady clearly doesn’t want her son to end up with someone who says Mars is in retrograde, whatever that means, and says that the planets guide them. Well, it’s safe to say they weren’t written in the stars.

“You’re Bed : – ) “

What is the weirdest message you have received from someone? We know this person’s answer would be when their landlord created and sent a 3D image of their bed. Her response is appropriate. We would’ve also responded, “It’s your, not you’re,” but we get that she was probably too creeped out to worry if his spelling was correct.

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We hope she moved out of her building and blocked the landlord because he’s just giving off creepy vibes. That smiley face in the text is just unsettling. We would like to know if they send all their tenants screenshots of 3D-rendered images they made of things in their apartment.

Notification from: Delulu Person

Texting can be great – it’s an easy way for people to get in contact. The downside is it makes it easier for stalker types to send you a message to tell you that they have been dating you in their head. How wonderful, we said sarcastically.

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We’re curious to know if, back in the day, people would send letters in the mail like this to someone, or did people only become strange and delusional after the invention of cell phones? People on TikTok have said, “Being delulu is the solulu” (being delusional is the solution,) but please don’t send messages like this to anyone.

Tasked Failed Successfully

Oh no! This one is giving us second-hand embarrassment. We wouldn’t be able to recover if we sent a screenshot of a message to the wrong person. Oh well, to look on the bright side, she did what she wanted to do; she rejected him. #Task failed successfully.

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We are honestly surprised that the guy didn’t respond with something horrible, as most people would. He’s not salty at all about it. You can almost feel his pain and hear the defeat. Sorry, we can’t help but laugh, though.

Message to I Heart Guinea Pigs

Looks like someone was super bored and decided to cure that by hating on a random Guinea Pig fan page account. They are so chaotic – we are living for it. The person they messaged probably could have been more impressed, though.

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We would like to know how they responded to their message, but we guess we’ll have to live without that information. So sad. Well, we could only imagine some harsh words were exchanged. When you love something, you will feel a strong need to defend it.

Girls Supporting Girls

Writer Kasia Gospos once stated, “Amazing things happen when women help other women.” In this instance, this lady is getting a free trip to Miami all because another lady helped her catfish someone. We’re all for girls supporting girls, but we also don’t condone catfishing.

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Did you know that, according to LegalJobs.Io, around 20,000 individuals are catfished annually in the US? Yikes, stay safe out there, people. Remember, if you suspect you’re getting catfished, video call them. And don’t pay for a trip for someone you’ve just been talking to online.

Barbecue Squirrel > Baby Girl

“That annoying moment when you’re texting someone and autocorrect decides to join the conversation.” Autocorrect does say the darndest things – like here, the guy wanted to say baby girl, but it changed it to barbecue squirrel. We must admit that we like that better.

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This is the best message we have ever seen. Everyone should start calling their significant others barbecue squirrels. Next time you get a message from your loved one, say this to them and wait for their reaction – it will be super funny.

Salty Message

Romance is dead, you guys. People used to receive love letters in the mail, and now all they are getting are weird, horrible Facebook messages from people who are already in relationships – just read this. We wouldn’t say this guy handles being ignored very well.

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We actually laughed way too hard at this one. What would you do if you got a message like this? We would most likely do what this person did – post it on social media for people to see and make fun of.

No Pets Allowed

Want to know what a typical conversation between a landlord and tenant looks like – well, here you go. You can complain to them over messages, but they will always change the subject, and nothing gets resolved. It is pretty frustrating.

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We bet that many New Yorkers have had a conversation almost exactly like this with their landlord – the rat problem is so bad in the Big Apple. Some of the three million rats have definitely made themselves at home in people’s apartments. And, of course, the landlords don’t care. It’s better to message an exterminator.


Oooh, here we have someone whose girlfriend now has receipts that they are a liar and a cheater. We wonder if their name is Peter ‘cause “Peter, Peter pumpkin eater had a wife and couldn’t keep her” well more like had girlfriend. 

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The one thing that really got us laughing was the sad face emoji that the person reacted with to the message. They know they have just been busted and have just become single. Too bad. We can’t say we’re sad, though. Serves him right!


This person decided to randomly send their grandma a pic of their dog’s toebeans with a text underneath saying “hands.” This is one of those instances when you think something is cute; take a picture of it but might delete it later. Who wouldn’t want to receive a message like this?

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If someone ever sent us a picture of their pup, we would heart it and say, “Aww.” His grandma just seemed confused, though. Imagine the image failed to send; she just received a message saying “Hands.” That would be hysterical.

No Happy Birthday Message For You

“Never back down, never what? Never give up.” That famous Tiktok sound is definitely this person’s motto. They keep trying to get a happy birthday message from someone, clearly not a close friend, even though they keep getting left on read.

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We hope they learn their lesson the next year and don’t wish them a happy birthday or tell them it’s theirs, hoping to get a greeting back. It would just be sad if every single year they keep doing this.


The award for the most bizarre response to a message goes to this person right here – we didn’t expect them to say what they said. Either they just responded without reading the message or genuinely think someone wants to purchase an item they feel promotes violence.

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Do you know what this message reminds us of? When you’re conversing with someone in person, and you tell them something serious or ask them a question, and they clearly don’t hear you, they laugh or smile. Yep, just like that, this person didn’t address what they were talking about.

Emotional Damage

“The worst thing they could say is no” sure, or they can tell you that you are ugly. If this person doesn’t laugh at this message, they will cry. They’ll probably never want to try asking another girl out ever again.

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We’re laughing at this message now, but if someone had to say this to us, we would feel, to quote the meme from comedian Steven He’s 2021 video, “emotional damage.” They really did this person dirty – they’re a savage.

Mortifying Message

Monkey covering eyes emoji – that is probably how this girl feels after receiving this message. Wouldn’t you be embarrassed and turn as red as a tomato if you received a text telling you that you charged your booty shorts to a company? We would.

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Out of everything this girl had to accidentally buy on the wrong card, it had to be booty shorts. Next time, she’ll definitely triple-check what card she’s using. We’re sure she wouldn’t want to get another message about booty shorts.

Knock Knock

We want to say we respect everyone’s religion, but we must admit that this message is quite funny. For those who don’t get it, Jehovah’s Witnesses don’t believe in celebrating Christmas. What they do believe in, is going door-to-door to teach others about their religion, hence this “knock knock” joke.

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We hope the other person didn’t actually pass on the knock-knock message to their friend. Imagine if they said, “Hey Beth, we just wanted to say knock knock.” Well, people have sent far more random and strange messages.

Jedi Mind Trick Fail

This one has got us cackling. This guy tried but failed miserably to try and trick a seller into accepting less than what he was willing to sell a product for, but the person was having none of it. Well, better luck next time, pal. 

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We thought about it, and maybe this person thinks he is capable of doing what the Jedi’s in Star Wars do; plant a suggestion in someone’s mind, known as the Jedi mind trick, or he just isn’t good with technology. We’ll never know.

Couple Goals

Tee-hee, this wife knows her husband so well – she knows that he wasn’t just trying to spice up their marriage; he just didn’t do his chores. We love this; it’s so hilarious. You know what else we like? The husband’s contact name for his wife is “The wife” with hearts. These two are couple goals.

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We think ninety percent of married people will find this conversation very relatable. That’s why investing in a dishwasher is good – you won’t have to message your spouse with excuses for not eating on plates that day.

Text From Bae

Here is someone who tried to message their other half for reassurance but found out that they will leave them if times get tough. That has to hurt. Well, what can we say – at least they being true to themselves.

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This is how all overthinkers think their bae will respond to them if they ask a question like this. Most wouldn’t dare to respond with this message, but this person seems like they want to be single. We’d be surprised if the relationship continued after this text.

Cheater Cheater

Britney Spears’s lyrics, “Don’t you know that you’re toxic” is a message that we would send to these two people here. These two belong on a reality show filled with toxicity and drama. Yep, we’d watch something starring these peeps.

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We would be very interested to know the conversation after they both admitted to cheating on each other. They need to, as people say, “spill the tea.” Their whole dialogue is probably just as laughable, pointless, and entertaining as this.

And Block

This is one unhinged person – they spammed someone with almost disturbing messages after they were ignored. If someone told us to answer them after they said they’re going to show up in our dreams like Freddy Krueger from the horror movie Nightmare on Elm Street, we’d be like, “Nah to the ah to the no no no.”

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If we were dealing with this person, our response would’ve been, “New phone, who dis?” Anyway, here’s to hoping the person who received this message blocked them, never heard from them again, and didn’t see them in their dreams either.

“Always a Boy Friend, Never a Boyfriend”

These are texts between a girl and her guy friend stuck in the friend zone. She called him “dude” in the message, which is normally an indication that a girl doesn’t romantically view the guy. Yup, that’s a telling sign.

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Someone once said, “Think of the friend zone as the safe zone. Friends are forever.” We don’t think this dude will even want to be friends after she texted him “No” after he told her he was single and hinted that he would date her. She should know that the heart emoji does not soften the blow.

“I’m Not Into Short Guys”

Here we have a screenshot of text messages between two people planning a date that is heartwarming – you’ll be saying you hear wedding bells for these two. Unfortunately, this guy can’t say he met his future wife online ‘cause he was probably ghosted after revealing his height.

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 The last message that was sent has us in stitches – could she be more obvious that she’s canceling the date because she doesn’t go out with guys under six feet? She missed out on a nice guy – he was prepared to let her pick the movie for their date.

Honesty is the Best Policy

Have you heard the lyrics, “And if you wondered if I hate you (I do),” from SZA’s 2022 hit song I HATE U? Well, those lyrics come to mind when reading this conversation. We have no doubt that the person who replied definitely believes in the saying, “Honesty is the best policy.”

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There is a Russian proverb, “Better to be slapped by the truth than kissed by a lie.” This person probably didn’t expect to be slapped when they messaged someone to ask if they hate them – we hope they can handle the truth.

Do Not Be Scared

What is your biggest fear? This person’s fear is international shipping, also known as “internshipphobia.”They said it in a text; “I don’t do international shipping, I’m afraid.” Just jokes. We know they meant to say they unfortunately don’t do international shipping, but we’re not sure the person they’re conversing with knew what they meant.

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We have a real jokester over here, or this person’s first language isn’t English – they said they live in Spain. Well, now we’re also in Spain, but the “S” is silent – we’re in pain from laughing too hard at this message. We just had to make that joke.


“Save the drama for your mama,” This lady here has clearly never heard that quote. As you can see from this message she received, she likes lying to others because she is bored. LOL, that is not good at all.

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We’ve probably all uttered these words before, “Bored in the house, and I’m in the house bored.” Most people just scroll on TikTok to eliminate boredom, but this lady was built differently – she finds spreading lies entertaining. Who knows how many messages she gets from guys asking why she’s telling people fiction?

Mentally Unstable but Hot

There’s a trend on TikTok where people talk about their Roman Empires – something they think a lot about. We think this person’s “Roman Empire” is probably when someone said that they are “Mentally unstable but hot.” We wouldn’t be able to forget or stop thinking about a message like this if we received it.

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If someone called us “mentally unstable but hot,” we wouldn’t know whether to be offended or take it as a compliment. We would probably just be left speechless – how do you even reply to a text like that? What do you say?

Ruining Childhoods One Message at a Time

There is a theory that Violet is not Bob’s child from The Incredibles. This person had to message someone to see if it was confirmed by asking if a redhead and a blonde can have a kid. The person’s answer: someone cheated. We must add that it wouldn’t be “someone,” it would be the mom.

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For those who are saying they ruined your childhood, don’t worry. Violet could’ve dyed her hair, and that’s why she looks so different from Bob. Only the creators of the movie know the truth, though. They should message them. Does anyone have their number? Now, that’s a conversation we would want to read.

Girlfriend? Who’s she?

What are the lyrics in Shawn Mendes’ song Treat You Better, again? Is it “I know that I can treat you better than I treat her”? Oh no, wait, sorry, that’s not it – that’s what this guy said in a message to someone. We hope it was forwarded to his girlfriend, who then dumped him.

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Why do people flirt over text with others when they are in a relationship? It’s just criminal. Jail to this guy for treating his girlfriend so badly. He is even aware that he isn’t treating her right. He gets points for self-awareness, but that’s it.


That awkward moment when you think someone is messaging you for a date, but instead, it’s only to let you know that you’ve been caught on video stealing something. Pfft, that is something that happens rarely.

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This conversation is cray cray. We really need to know what their response was. Is this even real, and if it is, why would they post it, and shouldn’t they have contacted the cops instead? Argh, so many unanswered questions! 

Meowtastic Message

This “car” is really purrfect, we wonder what kind of model it is. What we do know is that the engine purrs and sometimes even hisses. Jokes aside, this cat is too cute; we would also want to show him off to everyone.

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What started as a cute message was quite funny because of their spelling error. Well, even if they didn’t accidentally say my “car” instead of cat, it still would’ve been quite hilarious as it seems they sent it randomly. Wouldn’t you find it funny if someone out of nowhere sent you a picture of their cat?

Unexpected Response

How not to flirt with someone 101; don’t send them a message saying, “I bet u wild in person” as you’re just setting yourself up for a sarcastic response. Remember that you can never go wrong with a simple “Hello, how are you?”

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Name someone less interested in having a convo with a person. They’ve made themselves sound less than desirable at the risk of sounding rude, so they wouldn’t want to continue talking to them—good for them and good riddance.

Discrimination is Not Ok

“Big mistake. Big. Huge!” That famous line from Pretty Woman certainly applies here. Like Julia Robert’s character Vivian in the movie was denied assistance at a clothing boutique, this lady was refused a gaming laptop. Like the snobby saleswoman, this guy lost out on a big sale.

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This man needs to spend a little less time sending discriminatory messages to women and a little more time studying good business practices – he just lost out on $450. We hope this girl told him, “Boy, bye,” and bought another gaming laptop and sent him a screenshot of her purchase.

World’s Best Most Toxic Dad

This dad is in his toxic era – he sent a message to his son saying that he must exclude a girl and make her feel bad just because she rejected him. That doesn’t seem like very good parenting to us.

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We don’t think this father should be teaching his son revenge tactics. The only one who needs to learn a life lesson is the dad – he needs to learn that you can catch more bees with honey than vinegar. Here’s someone you shouldn’t look up to.


We’re wrapping up this post with a complisult. According to the Urban Dictionary, it is “When one makes a statement to another that is part compliment, part insult. Yep, this message is a complisult alright. Some people have no idea how to charm others.

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This person has to learn to take the good with the bad – they should accept people’s positive and negative traits without being critical. They also need to know that it’s not polite to send messages to people calling them insane. Thanks for coming to our TedTalk.