53 Jokes For Hey Guess What

Updated on: Apr 16 2025

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Once upon a time in the whimsical town of Wordplayville, a group of friends decided to throw a surprise party for their friend, Sam, who was known for his love of puns. The setting was perfect—a venue decorated with giant letter balloons and a banner that read, "Hey, Guess What: Puntastic Party Ahead!"
As guests started arriving, whispers of puns filled the air. The excitement was palpable, and everyone was eagerly awaiting the guest of honor. When Sam finally walked in, the room erupted into cheers, "Hey, guess what, Sam? We've got a pun-derful surprise for you!"
The main event unfolded with a series of pun-tastic activities. From a "Pun-derful Costume Contest" to a "Guess the Pun" game, the laughter echoed through the venue. Sam, the pun maestro himself, couldn't stop cracking up at the clever wordplay that surrounded him. The pinnacle of hilarity came when someone accidentally spilled a bowl of alphabet soup, creating a literal "spill of the letters." It was a soup-er moment, indeed.
As the night drew to a close, Sam thanked everyone for the punbelievable party. Little did he know; the night ended on a high note when the friends handed him a trophy shaped like a quill with a note that read, "You're the Pun-dit of Wordplayville!"
In the bustling city of Techtopia, a group of coworkers decided to play a prank on their colleague, Alex, who was known for mixing up text messages. They devised a plan to send a series of confusing messages throughout the day, all beginning with the phrase, "Hey, guess what."
The main event kicked off when Alex received a text saying, "Hey, guess what? The boss wants you to lead a meeting in pig Latin ASAP." Bewildered, Alex stumbled through the meeting, trying to decipher the oink-filled chaos that ensued. Little did he know that each "Hey, guess what" message added a layer of absurdity to his day.
The hilarity reached its peak when a message arrived saying, "Hey, guess what? You're getting a promotion—just kidding! April Fools'!" Laughter erupted from the entire office, and Alex, though initially confused, couldn't help but join in on the joke. The coworkers revealed the prank, and everyone shared a good-natured laugh, turning the chaotic day into a memorable office legend.
Deep in the heart of Adventureland, a group of friends decided to organize a surprise safari for their nature-loving buddy, Max. The theme was clear: "Hey, guess what—you're about to embark on a wild adventure!"
The main event kicked off with the friends leading Max blindfolded into a makeshift jungle. Sounds of rustling leaves and faux animal roars surrounded them. The friends, dressed as safari guides, narrated Max's journey with over-the-top enthusiasm.
As the safari unfolded, a series of comical mishaps ensued. One friend, disguised as a lion, accidentally tripped over a tree root. Another, attempting to be a stealthy gorilla, got stuck in a makeshift vine. The exaggerated reactions and slapstick comedy turned the surprise safari into a hilarious spectacle.
The climax came when they unveiled the grand finale—a "wild" encounter with a giant inflatable giraffe. Max, initially startled, couldn't help but burst into laughter. "Hey, guess what—you're now officially the fearless explorer of our wacky wilderness!" the friends declared, presenting Max with a safari hat and a trophy shaped like a mischievous monkey. It was a surprise safari that left everyone roaring with laughter and Max with memories of an adventure unlike any other.
In the quaint town of Sweetville, a group of friends decided to surprise their friend, Emily, with a cake decorating contest for her birthday. The theme was simple: "Hey, guess what—life is sweet!"
The main event unfolded with flour flying and frosting smeared across the kitchen. As the friends engaged in a friendly competition, the cakes took on a life of their own. One friend misheard the theme and created a cake shaped like a giant pair of feet. Another mistook "sweet" for "street" and crafted a cake resembling a cityscape.
The laughter escalated when the doorbell rang, and Emily's grandmother, who was hard of hearing, entered the chaos. Seeing the peculiar cakes, she exclaimed, "Hey, guess what? This must be the bakery's avant-garde collection!" The friends burst into laughter, realizing the unintentional masterpiece they had created.
In the end, the cake catastrophe turned into a sweet success as they presented Emily with a cake collage that captured the spirit of their misadventures. It was a birthday celebration filled with laughter, sugar, and the sweet taste of unexpected creativity.
I tried turning the tables once. Someone said, "Hey, guess what?" And I confidently replied, "You got a pet dinosaur!" Spoiler alert: they did not have a pet dinosaur. They had a hamster named Rex. Close enough, right?
And then there's the suspenseful pause before they spill the beans. It's like waiting for a punchline, but the setup is your own anxiety. "Guess what? I forgot to buy milk." Really? That's what we're doing now? I was prepared for espionage-level secrets, not your dairy aisle drama.
You ever notice it's never anything straightforward? It's never like, "Hey, guess what? I just found a dollar on the street." No, it's always a saga. It's like, "Hey, guess what? I accidentally joined a biker gang for 15 minutes today. Turns out, they just wanted directions to the nearest Whole Foods."
And why do we even bother guessing? It's not like we're ever close. They might as well say, "Hey, guess what? I won the lottery, became a ninja, and discovered a cure for the common cold." And you're sitting there like, "Um, you got a new haircut?
And why is it always "hey, guess what"? Can't we mix it up a bit? Spice things up with a "Yo, check this out" or a "Hold onto your socks"? Nah, it's forever going to be the underwhelming "hey, guess what." Maybe one day someone will throw a curveball and go with "hey, guess why." That would really mess with our heads.
Hey, guess what? Why don't skeletons fight each other? They don't have the guts.
Hey, guess what? I asked the librarian if the library had any books on paranoia. She whispered, 'They're right behind you.
Hey, guess what? Parallel lines have so much in common. It's a shame they'll never meet.
Hey, guess what? I used to play piano by ear, but now I use my hands.
Hey, guess what? I told my computer I needed a break, and now it won't stop sending me vacation ads.
Hey, guess what? I told my friend 10 jokes to make him laugh. Sadly, no pun in ten did.
Hey, guess what? I told my computer I needed a break, and now it won't stop sending me vacation ads.
Hey, guess what? I used to be a baker because I kneaded dough.
Hey, guess what? I'm on a whiskey diet. I've lost three days already.
Hey, guess what? I used to be a baker, but I couldn't make enough dough.
Hey, guess what? I'm reading a book on anti-gravity. It's impossible to put down.
Hey, guess what? I asked the librarian if the library had any books on paranoia. She whispered, 'They're right behind you.
Hey, guess what? I'm on a whiskey diet. I've lost three days already.
Hey, guess what? I only know 25 letters of the alphabet. I don't know y.
Hey, guess what? I used to be a baker because I kneaded dough.
Hey, guess what? I'm reading a book on anti-gravity. It's impossible to put down.
Hey, guess what? I only know 25 letters of the alphabet. I don't know y.
Hey, guess what? I told my wife she should embrace her mistakes. She gave me a hug.
Hey, guess what? Parallel lines have so much in common. It's a shame they'll never meet.
Hey, guess what? I'm reading a book about anti-gravity. It's uplifting.

The Tech-Challenged Grandparent

Navigating the world of modern technology
Hey guess what? I downloaded an app to organize my apps... and now I can't find the app that organizes my apps. It's an app-ocalypse!

The Culinary Disaster

Attempting to cook with questionable skills
Hey guess what? I made a cake today! It was so dense, I think it’s applying for a job as a doorstop.

The Overworked Office Worker

Juggling a million tasks at once
Hey guess what? I'm the Picasso of chaos. I once managed to staple my grocery list to an important report. Procrastination level: masterpiece!

The Forgetful Parent

Trying to remember something amidst the chaos
Hey guess what? I found the solution to my forgetfulness! I tied my keys to my phone... now if only I could remember where I put my phone.

The Socially Awkward Extrovert

Navigating social situations with less-than-stellar finesse
Hey guess what? I attempted to break the awkward silence by telling a joke... only to realize it was on mute the entire time. The silence remained unbroken but awkwardness peaked!

Hey Guess What - The Cryptic Message

Hey, guess what? is the beginning of every conversation that makes you question your life choices. You're left deciphering a code, trying to figure out what they mean. Guess what? The potato is in the mailbox. I have no idea what that means, but I'm concerned for that potato.

Hey Guess What - The Unwanted Trivia

Whenever someone starts with Hey, guess what? I brace myself for irrelevant trivia. Guess what? Elephants are the only animals that can't jump. Oh, great, now I have a random fact taking up space in my brain, and I can't even use it to impress anyone.

Hey Guess What - The Letdown Symphony

Hey, guess what? is the overture to the grand symphony of letdowns. It's like they hand you a violin, expecting you to play along with their mundane melody. Spoiler alert: I don't even know how to play the letdown violin.

Hey Guess What - The Anxiety Inducer

You know what's worse than a horror movie? When someone leans in and goes, Hey, guess what? I'm like, No, please, spare me. Is it a ghost? Is it a tax audit? What is it? It's like they're holding your curiosity hostage, and you have to pay the ransom with forced enthusiasm.

Hey Guess What - The Unsolicited Update

Why do people think I need constant updates on their lives? Hey, guess what? I finally organized my sock drawer. Oh, thank goodness! I've been losing sleep over the state of your sock drawer. I mean, who even has time for sock drawer drama?

Hey Guess What - The Conversation Killer

You know what really kills a conversation? Hey, guess what? It's like a nuclear bomb for small talk. Suddenly, everyone's staring at you, waiting for a groundbreaking revelation. Newsflash: My life is not that interesting.

Hey Guess What - The Anti-Climax Expert

You ever notice how Hey, guess what? is the prelude to the most anti-climactic stories? Guess what? I found a dollar on the street. Oh, the suspense was killing me. I was hoping for a lost treasure or a secret government conspiracy, but no, just a lucky buck.

Hey Guess What - The Expectation Setter

Hey, guess what? is the phrase that sets expectations sky-high. You're ready for breaking news, but most of the time, it's just breaking boredom. Guess what? I changed my shampoo. Oh, fantastic! I was on the edge of my seat, wondering when this thrilling saga of hair care would unfold.

Hey Guess What - The Social Experiment

Hey, guess what? is like a social experiment where you pretend to be interested. You nod, smile, and act surprised, but deep down, you're just hoping they finish their story so you can get back to pretending to work.

Hey Guess What - The Universal Setup

Alright, so someone comes up to you and says, Hey, guess what? and you instantly feel like you're in the middle of a suspense thriller. I'm waiting for them to drop the bombshell, but it's more like a pop quiz on someone else's life. Hey, guess what? Brenda from accounting got a cat. Oh wow, life-altering news. Thanks for the adrenaline rush.
The only thing worse than getting a "hey guess what" text is sending one and then realizing you have absolutely nothing interesting to follow it up with. It's like starting a firework show and then realizing you only brought sparklers.
Hey guess what" is the text equivalent of a clickbait headline. You open it, hoping for some juicy gossip, but instead, it's just your friend informing you that they successfully parallel parked. Riveting stuff.
Hey guess what" is the text version of a drumroll, but instead of building anticipation for something grand, it's building up to the revelation that your friend finally learned how to tie their shoes. I mean, come on, I was expecting fireworks, not a tutorial on basic life skills.
Hey guess what" is the adult version of that kid in class who raises their hand and says, "I have a secret, but I'm not telling anyone." Just spill the beans already! We're not in middle school, and I've got things to do.
You ever get a "hey guess what" text and immediately regret every life decision that led you to this moment? It's like signing up for a surprise party, but the surprise is that you're now responsible for planning the next one.
Hey guess what" is the modern-day version of the carrier pigeon. Instead of delivering important messages, it brings you updates on the most mundane aspects of someone else's day. Next time, just send an email.
Getting a "hey guess what" text is like playing Russian roulette with your attention span. Will it be something mildly interesting, or will it be a three-paragraph saga about someone's pet goldfish learning a new trick? The suspense is killing me, and not in a good way.
You ever get that text from someone that just says, "hey guess what"? And you're sitting there thinking, "Oh great, now I'm stuck in a suspense thriller, starring me, trying to figure out what on earth they're about to drop on me. Spoiler alert: it's usually something like 'I ate the last slice of pizza.'
Hey guess what" is like the opening line of a conversation that's about as thrilling as watching paint dry. It's like, why not just cut to the chase and tell me what's up? "Hey guess what" should come with a warning sign: "Prepare for a mediocre story ahead.
You ever notice that "hey guess what" is like the prelude to the world's least exciting game show? You're the contestant, and the prize is finding out which mundane thing happened to someone else. "Congratulations! You've won the thrilling revelation that Karen bought a new toaster!

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