300+ Weird Questions You Just Can’t Miss

Now, if you’re anything like me, you’ve probably found yourself at a social gathering, clutching a drink, searching the room with a mild sense of panic for something—anything—to say. And that’s when it hits you: the weird questions lifeline. Because, let’s face it, sometimes asking, “What’s your favorite color?” just doesn’t cut the mustard.

I’ve sailed these strange seas more times than I can count, dropping anchor in the most awkward of silences and diving headfirst into the abyss of the bizarre.

I’ve asked friends if they’d rather have spaghetti for hair or sweat maple syrup—just to see their puzzled expressions turn into grins. 

Weird Questions to Ask Your Friends

Ever find yourself in the midst of a lull during a hangout? I sure have. I once asked my friend if they’d prefer to have fingers as long as their legs – talk about a conversation dead-end.

But, if you dare to dive into the peculiar, here are some oddballs to toss at your buddies:

• If you could swap lives with any cartoon character, who would it be and why?
• What’s the strangest thing you’ve ever eaten for breakfast?
• Have you ever believed in a conspiracy theory? If so, which one?
• If your life was a TV show, what would the theme song be?
• Would you rather have a pet dinosaur or a dragon, and what would you name it?
• What’s the weirdest smell you actually enjoy?
• If you had a time machine, would you go back in time or into the future?
• Would you rather fight one horse-sized duck or a hundred duck-sized horses?
• What’s the most bizarre dream you remember having?
• If you could have an unlimited supply of one thing for the rest of your life, what would it be?
• If you could have an unlimited supply of one thing for the rest of your life, but it had to fit in your pocket, what would it be?
• Imagine your life is now a TV show. What genre would it be and which actor would play you?
• Would you rather have a rewind button or a pause button on your life?
• If you could morph two animals to make one super animal, which two would you choose and what would be their powers?
• If your personality was a city, which city would you be and why?
• What’s the most bizarre thing you’ve ever done just because you were bored?
• If you could ask your pet three questions, what would they be?
• In an alternate universe where you are a mythical creature, what would you be and what magical power would you possess?
• If you could replace all of the grass in the world with something else, what would it be and why?
• If you had to wear a costume every day for a year, what would you pick and what would be your backstory?

Weird Questions to Think About

On a solo stroll or just daydreaming? Ponder over these:

• If you could erase one event from history, which would it be and what do you think would happen?
• Is a hotdog a sandwich, and why or why not?
• If you could add one thing to a “Room of Requirement”, what would it be?
• How would you survive a zombie apocalypse in a grocery store?

• What would you do if you were the last person on Earth for one day?
• If you could hear every conversation around you for a day, would you want to?
• How would you use a superpower to make your daily life more convenient?
• What’s a magical power you would not want?
• If you found out life was actually a simulation, would you want to escape it?
• If languages could be tasted, what do you think English would taste like?
• If time travel becomes possible, who would be responsible for the time-traveler’s etiquette handbook and what would be the first rule?
• If you could see a specific color as another color entirely, which color would you switch and why?
• Suppose you wake up as the main character in the last book you read. How does your day go?
• If every time you snapped your fingers you could make one inanimate object come to life, which object would you animate first?
• What if shadows actually reflected an alternate reality, what do you think your shadow is doing right now?
• Imagine if it rained something other than water. What would you want it to rain and how would it change the world?
• If you had the power to delete one word from existence, which word would you choose and what do you think the consequences would be?
• If you could transform into an inanimate object for a day, what would you be and what would you do?
• If humans could naturally change their hair color at will, how do you think this would affect fashion trends and hairstyles?
• What if one day the internet suddenly became sentient. What’s the first thing you’d ask it?

Weird Questions to Ask a Kid

As a mother of two, I’ve discovered the art of conversation lies not just in the questions we ask, but in the way we ask them. Gone are the days when I would only inquire about school and homework. 

Now, I sprinkle our dialogues with weird and wonderful questions that tickle the imagination and coax out giggles and wide-eyed wonder.

Why do I do this? It’s simple. By asking my child offbeat questions, I show her that I’m not just a mom who’s all about rules and routines, but also someone who values creativity and fun. 

These quirky questions become a bridge, connecting my world to hers. They encourage her to see me not just as a parent, but as a person who is genuinely interested in exploring the whimsical corners of her mind.

This approach has an unexpected and delightful consequence: she opens up. Through these playful exchanges, she shares the vibrant tapestry of her daily experiences—stories about her friends, the latest playground escapades, and even the occasional worry. 

These moments are golden. They assure me that while I might sometimes embarrass her with my unexpected queries, I’m also building a relationship where she knows her thoughts and feelings can flow freely, as colorful and surprising as the questions I ask.

• If your stuffed animals could talk, what would they say?

• If you could grow anything in the garden, what would you grow?
• Can you describe the color yellow to someone who’s never seen it?
• What do you think clouds taste like?
• If you could ask your pet three questions, what would they be?
• What’s the best way to make friends with a dragon?
• If you were a mad scientist, what experiment would you run?
• What’s the funniest word you know?
• Do fish ever get thirsty?
• If you were a superhero, what would your sidekick be like?
• If your stuffed animals could talk, what do you think they’d say?
• If you could build anything out of candy, what would you build and why?
• Imagine if you had a dinosaur as a pet. What kind of dinosaur would it be and what would you name it?
• If you could make up a brand new school subject, what would it be and how would it be taught?
• What superpower do you think would be the most fun to have at the playground?

• If you could change the sound your voice makes, what new sound would you choose?
• If you could grow anything on trees, besides fruit, what would you want it to be?
• If you were a wizard, what would be the first spell you would try to cast?
• If you could jump into any painting and explore, which one would it be?
• What do you think is at the end of the rainbow?
• If you could invent a new flavor of ice cream, what would it taste like and what would you call it?
• If animals could talk, which one do you think would be the funniest to have a conversation with?
• If you had a robot that could do one chore for you, what would it be?
• What would you do if you found a treasure map in our backyard?
• If you could create a new holiday, what would it celebrate and what traditions would it have?
• What kind of magical powers do you think your favorite toy has?
• If you could change the school mascot to any creature, real or mythical, what would it be?
• Imagine if you could build a house out of dessert, what sweet treats would you use?
• If you could make your own planet, what would you name it and what would it be like?
• What would you pack in your suitcase if you were going on a trip to the moon?

Weird Questions to Ask Reddit

Reddit is a weird and wacky playground, and I’ll be the first to admit that I’m the kid who’s still figuring out the slides from the swings. This place is huge, filled with people chatting about, well, everything under the sun. 

Some folks seem to have the map of this place tattooed on their brains, while I’m over here walking into subreddits like unexpected doors, never quite sure if I’ll find a room of cat memes or a space debate.

And yet, even though it’s a bit of a head-scratcher, I keep on coming back. It’s like a treasure hunt where you’re not always sure what the treasure is, but the search is too much fun to stop. 

I know there are loads of others like me on Reddit, sometimes just lurking in the background, sometimes jumping into the fray, all of us together in this strange, curious corner of the internet.Here’s what I might throw into the mix:

• Redditors, what’s the most bizarre unsolved mystery you know of?
• Has anyone ever experienced something that they think could be a glitch in reality?
• What’s the worst advice you’ve seen upvoted here?
• If every username suddenly became a real person, who would you be most afraid of?
• What’s the weirdest subreddit you’ve stumbled upon and why?
• If your life was a video game, what would some of the cheat codes do?
• What’s the most creative use of emojis you’ve ever seen or can come up with?
• If you could have any mythical creature as a pet, what would it be and why?
• What’s a completely ridiculous conspiracy theory that you can invent on the spot?
• If you had to eat one type of food from a video game or TV show for the rest of your life, what would it be?
• What would the ‘boss level’ of your day look like and how would you beat it?
• If social media platforms were represented as characters at a party, how would you describe each one?
• What would your dream amusement park be like if it were themed after your favorite hobby or interest?
• If you could swap lives with a historical figure for one week, who would you choose and what would you do?
• How would you explain the concept of a ‘meme’ to someone from the 1800s?

Weird Questions to Ask Someone

The first time I met a group of moms, I blurted out, “Do you ever regret becoming a mom?” The silence that followed was… educational. Here are some less polarizing questions:

• If you had to wear one color for the rest of your life, what would it be?
• What’s a song that you hate but can’t help singing along to?
• If you could have dinner with any historical figure, who would it be?

• What’s the weirdest gift you’ve ever received?
• If you could transform into any mythical creature, which one would you choose?
  
• If you were a Disney princess, what funny questions would you ask your animal sidekicks?
• What’s the weirdest thing you’ve ever done with peanut butter?
• Can you tell me about the last time a fictional character influenced a major decision in your life?
• What’s the most embarrassing thing you’ve ever said to someone on a first date?
• If you had to eat one favorite food every day for the rest of your life, what crazy question would you ask the chef?
• Imagine your best friend just turned into a mythical creature. What’s the first silly question you would ask them?
• When was the last time you told a hilarious lie about something mundane, like the expiration date on milk?
• What’s the best way to start a good conversation with a group of friends using only open-ended questions?
• Have you ever had a dream about a historical figure where they shared some thought-provoking question with you?
• If you could compose a theme song about the weirdest dream you’ve had, what would the chorus be?
• Which fictional character do you think would make the worst roommate, and what fun questions would you ask to find out?

• On a deserted island, what’s the one inanimate object you’d bring, and what would you name it?
• Have you ever encountered a strange rumor about yourself that turned out to be a good weird question for a romantic relationship?
• What’s the most interesting thing you’ve learned from a completely random weird question?
• If you were a mad scientist, what silly experiment would you conduct to understand why people love their favorite ice cream flavor so much?

• What’s the weirdest question you could ask a famous person that would give you a good sense of their humor?
• If you could have a pet dinosaur, what would be the first thing you’d train it to do for a fun way to impress your close friends?
• Can you think of any unwritten rules for what to do when you hear the worst song of all time in a public place?
• If you were in a horror movie, what would be the one thing you do that would make the audience scream, “No, don’t do that!”?
• Imagine if life had an ‘undo’ button. What’s the first thing you’d redo for a great conversation starter?

Weird Ice Breaker Questions

Ice breakers: the necessary evil of every group setting. Next time, instead of the usual “What do you do?”, try:

• Would you rather have a rewind button or a pause button on your life?
• What’s the weirdest food combination you enjoy?
• If you could ask a wild animal one question, what would it be?
• If your life was a genre of music, what would it be?
• What’s the most interesting thing you’ve seen this week?
• If you could only communicate using one word today, what word would you choose and why?
• Imagine you’re an alien visiting Earth for the first time. What would you find most bizarre about human behavior?
• If animals could talk, which species would be the rudest of them all?
• Would you rather have fingers as long as your legs or legs as short as your fingers?
• If you were a vegetable, which one would you be and what would you say to people who don’t like to eat their veggies?
• What’s the most unusual place you’ve ever taken a nap?
• If your life was a video game, what would some of the cheat codes be?
• Suppose you’re a mad scientist, what scientific experiment would you run if money and ethics weren’t an issue?
• What’s the most imaginative name you can think of for a pet rock?
• If you could instantly become an expert in something, what would it be, and what’s the first weird thing you’d do with your new knowledge?
• Can you think of a conspiracy theory involving something mundane, like socks disappearing in the laundry?
• If you had to wear a T-shirt with just one word on it for an entire year, which word would you choose?
• What would be the absolute worst name you could give to a dating app?
• If you were a flavor, what would you be and how would you describe yourself to someone who has never tasted that flavor before?
• What’s the most creative use for a stapler that doesn’t involve stapling?
• If you could replace all of the grass in the world with something else, what would it be and why?
• Imagine you’re a DJ at a club where you can only play TV show theme songs. Which is your go-to track to get the party started?
• If you could have a mundane superpower, like being able to turn any water fountain into your favorite beverage, what would it be?
• If a biopic were made about your life, which actor would you not want to play you, and why?
• If you had to fight one hundred duck-sized horses or one horse-sized duck, which would you choose and what would be your strategy?

Related : Ice breaker games for middle school

Weird Interview Questions with Answer

In an interview, I once asked the interviewer if they’d ever apply for the job I was interviewing for. Awkward? Yes. But it can reveal a lot about the role. Here’s a sample with a twist:

• Question: How would you sell a fridge to an eskimo? I’d focus on its ability to protect food from polar bears and preserve non-frozen items. This tests the candidate’s ability to think outside the box and sell a product irrelevant to the customer’s environment.
• Question: If you were a brand, what would be your motto?“Endurance and adaptability in all endeavors.”
• Question: How would you sell hot chocolate in Florida in the summer?“By marketing it as a comforting, air-conditioned escape from the intense heat.”
• Question: If you could be any character from literature, who would you be and why?“Sherlock Holmes, for his exceptional problem-solving and analytical skills.”

• Question: How many basketballs would fit in this room?“By estimating the volume of the room and a basketball, I would calculate the number based on those dimensions.”
• Question: If you were an inanimate object, what would you be and why?“A book, to be filled with knowledge and share it with others.”
• Question: Tell me how you would make a tuna sandwich in space.“I would use magnetic trays to keep ingredients in place and rely on sealed packets to contain the food.”
• Question: If you were a salad, what kind of dressing would you have?“Balsamic vinaigrette for its versatility and ability to complement different ingredients.”
• Question: Imagine you’re a new addition to a crayon box, what color would you be and why?“Mystic Silver, because it’s unique and adds a spark to any picture without overpowering other colors.”
• Question: If you had to choose a song to play every time you entered a room, what would it be and why?“‘Eye of the Tiger’ for its energetic and motivational tone that could set a positive mood for any meeting.”

Funny Weird Questions

Life’s too short for boring questions. Sprinkle some of these into your dialogue diet for a good laugh:

• If you were a villain, what would your evil scheme be?
• What’s the most ridiculous fact you know?
• If animals could talk, which would be the rudest?
• What’s the funniest thing you’ve ever seen someone do in public?
• If you could only eat one food for the rest of your life, but it had no health consequences, what would you choose?
• If you were a musical instrument, what gossip would you spread about the piano?
• What’s the craziest thing you’ve ever done with a stapler?
• If your favorite holiday had a sense of humor, what joke would it tell?
• What’s the weirdest question you’ve been asked that actually made you think for a long time?
• How would you use a fairy tale to explain high school to someone who’s never been?
• If your life was a beautiful island, what would be the one “worst thing” you’d ban from it?
• In the story of your life, what would be the title of the chapter about your last birthday?
• What’s a good conversation starter for talking to a statue?
• If you found out your favorite food had a secret life, what do you think it would be doing?
• What’s the strangest rumor you’ve heard about what happens to your body parts when you sneeze?

Weird Questions About Life

On my first date with the guy who’d become my husband, I skipped the small talk and went straight for the big questions. Instead of the usual chit-chat, I asked him to choose between having kids or enjoying endless vacations. It was a weird question, but hey, it worked! He stuck around, and now we laugh about how that quirky question was the start of everything for us.

• If life were a video game, what would some of the cheat codes be?
• Is a hotdog a sandwich, and why or why not?
• If you could add one thing to a “Room of Requirement”, what would it be?
• How would you survive a zombie apocalypse in a grocery store?
• What would you do if you were the last person on Earth for one day?
• If our purpose in life is a tale we write ourselves, what theme do you want your story to convey to the world?
• How would our understanding of life change if we discovered sentient life elsewhere in the universe?
• In what ways do you think the pursuit of happiness differs from the pursuit of meaning in one’s life?
• If you could know the absolute truth to one question about your life’s path, what question would you ask?
• How would society change if we all knew the exact date of our passing and could see a countdown?
• If life is a journey, what kind of traveler are you – one who sticks to the map or one who thrives on the unexpected detours?
• Do you believe that our dreams have a purpose in our waking lives, and if so, what do you think that purpose might be?
• If you could inherit a single quality or talent without effort, would you feel it as an accomplishment or a stolen victory?
• What do you think would happen if humans evolved to a state where emotional pain was no longer felt?
• If you could send a message back in time to your younger self about what truly matters in life, what would you say?

Weird Personal Questions

Personal questions can be the weirdest, especially when they catch someone off guard. Here’s a sample:

• What’s the weirdest habit you have that you think no one else has?
• If you could instantly learn any one skill, what would it be and why?
• Have you ever had a dream that predicted something in your life?
• If you could choose any name for yourself, what would it be?
• What’s the strangest thing you’ve done while your brain was on ‘autopilot’?

Weird Siri Questions

Even artificial intelligence isn’t safe from the oddities of human curiosity. Just for fun, ask Siri:

• Siri, what does the fox say?
• Do you have any pets?
• Why do you vibrate?
• Can you beatbox for me?
• What’s your favorite color?
• Siri, what do you think about when you’re not helping us?
• Can you tell me a secret that you’ve never told anyone else?
• Siri, do you ever wish you could switch places with a human for a day?
• What’s your favorite conspiracy theory, Siri?
• If you had to pick a new voice for yourself, what would you choose?
• Siri, can you write a haiku about what it’s like to be a virtual assistant?
• If you could add one feature to yourself, what would it be?
• Siri, what do you think cats dream about?
• Do you consider yourself more of an optimist or a pessimist?
• What’s the weirdest request you’ve ever received from a user?

Weird Unanswerable Questions

Some questions are designed not to be answered but to perplex. These are great for late-night musings or deep conversations:

• Why do we dream?
• What is the sound of one hand clapping?
• If the universe is expanding, what is it expanding into?
• Can you have a thought without language?
• Is it possible to have a new color, and if so, what would it look like?
• If we could see air, would we still be able to see through it?
• Why do we have a word for ‘nothing’ when ‘nothing’ is the absence of anything?
• Can our thoughts be completely original, or are they just recombinations of everything we’ve experienced?
• Is it possible to imagine a new sense that humans don’t have?
• If the universe is constantly expanding, what is it expanding into?
• Why is ‘abbreviated’ such a long word?
• If you try to fail and succeed, which one did you actually do?
• Can silence be considered a sound if it’s the absence of sound?
• If every rule has an exception, is there an exception to that rule?

Crazy Questions to Ask People

These are the questions that make people give you “the look,” but they’re also the ones that can lead to the most memorable conversations:

• If you were a mad scientist, what scientific experiment would you run?
• Would you rather live in a world where dinosaurs never went extinct or a world where magic is real?
• If you had to be haunted by a ghost for the rest of your life but could choose which dead person it would be, who would you choose?
• What inanimate object do you wish you could eliminate from existence?
• If you could switch two movie characters, what switch would lead to the most inappropriate movies?

Remember, the point isn’t to have all the answers; it’s to enjoy the weirdness of the questions.

So go ahead, embrace your awkward side and let the strange tides of conversation take you where they may.

Who knows, you might just find that these weird questions not only break the ice but melt it away entirely.