241 Crazy Questions: Sharpen Your Mind & Surprize Your Fellows

241 Crazy Questions: Sharpen Your Mind & Surprize Your Fellows

Enliven the conversation with some of these 241 Crazy questions to ask your friends and other fellows! Whether you have a long history with someone or just met someone new, these 241 Crazy questions will bring laughter and can even lead to more meaningful conversations.

If you make it through the whole list, kudos to you! You surely will have gained a better understanding of your peers. The classic questions about school, work, and hobbies can get old and only scratch the surface of what makes someone unique

You might think you know someone well until you begin asking them these Crazy questions. For example, you may mind out that your friend may have a bizarre hidden talent or even a secret phobia.

Use our list of 241 Crazy questions to ask as a guide to reinforcing connections with your friends, family, coworkers, etc. Just be careful…any of these crazy questions you ask could come right back at you—so be ready.


241 Crazy Questions: Surprize Your buddies

  1. What would you do if you found a dead body in a hotel room?
  2. If bald people work in a restaurant, do they still need to wear a hairnet?
  3. Which one would you prefer: have no nose but have really good smelling fingers or be blind but have a really nice smile?
  4. If you have described something as indescribable, haven’t you already described it?
  5. Why is it called “beauty sleep” even though you wake up looking like a hot mess?
  6. What has been the most embarrassing thing you’ve ever worn?
  7. Which one would you choose: be alive and alone or about to die with a group of friends?
  8. How many pennies do you think would fit into this room?
  9. Should a man about to be executed in the electric chair be saved if he had a heart attack?
  10. Do you think if anything is possible, it’s still possible for anything to be impossible?
  11. Is it possible to hear someone’s iPod while they‘re running at maximum speed?
  12. Have you ever attempted to swallow toothpaste?
  13. What music would you choose to play every time you walk into a room?
  14. Do fish have a thirst for water?
  15. Is there a limit to how intelligent a single person can be?
  16. Why is sandwich meat round when bread is square?
  17. who’s the fifth person on your missed calls?
  18. If man developed from monkeys, why do we still have monkeys?
  19. Which would be the nicest if animals could only talk?
  20. If you punch yourself in the face and it hurts, are you weak or strong?

250 Crazy Questions

  1. What’s your most hated mode of transportation?
  2. If there’s an ambulance on its way to save someone and it knocks down someone, would it stop to help them?
  3. If you had the chance to invent a country, what would you name it?
  4. Have you ever taken something out of your possession and failed to return it?
  5. How would you be able to solve problems if you were from Mars?
  6. What are two things that you think are normal, but become really strange when you do them repeatedly?
  7. Is it permissible for minors who act in R-rated films to see them?
  8. What’s the color of the mirror?
  9. What do you usually think about while you are on the toilet?
  10. Which superpower would you not want?
  11. What hair color do they list on your driver’s license if you’re bald?
  12. How do birds actually pee?
  13. Will someone ever be able to live forever?
  14. You have discovered a beautiful island upon which you may build your own society and you can even make the rules. What’s going to be the first rule you’ll put into place?
  15. Why do you perceive everyone driving faster than you as an idiot and those who are quicker than you as morons when?
  16. Why aren’t they using blanks if it’s friendly fire?
  17. To kill an elephant, how many chickens would be required?
  18. If you took out a ship and changed all of its parts until none of the original parts are intact anymore, is it still the same ship or a totally different one?
  19. Is it possible that morality is derived from morons, just as electricity is derived from electrons?
  20. Have you ever unwrapped and rewrapped a gift bearing your name?

Strange Questions

  1. Why is it that lemon juice has an artificial flavor while dishwashing liquid has real lemons?
  2. Why do you think are manholes round?
  3. Are eyebrows also considered facial hair?
  4. Is your time truly wasted if you enjoy wasting it?
  5. What’s your favorite pooping position?
  6. When you know the battery is dead, why do you press harder on the remote control?
  7. Which individual, corporation, country, or organization would you bankrupt if you had the chance?
  8. Have you ever been tempted to sleep inside the fridge?
  9. In 2050, what will be the fastest mode of transportation?
  10. Which famous celebrity would you want to punch in the face?
  11. Male ballerinas are referred to as what?
  12. Is it safe for someone to park their vehicle near a fire hydrant if it is on fire?
  13. Do you think cavemen experienced nightmares about cavewomen?
  14. What is the shape of your peripheral vision?
  15. Which side of the armrest is really yours at a movie theater?
  16. Why do you think are blueberries not bright blue?
  17. Do you really want someone to give you an honest answer when you ask them how they’ve been?
  18. Suppose you have been given an elephant and you can’t give it away or sell it. What would you do with it?
  19. Why do you lower the volume on the radio when you’re driving and looking for an address?
  20. Is it a hostage situation if a person with several personalities threatens to kill himself?

241 Crazy Questions: List Continued.

  1. Why is it so difficult for women to apply mascara with their mouths closed?
  2. How many pairs of underwear do you actually own?
  3. What characteristics would your nemesis have if you had one?
  4. What is the highest number that anyone has ever counted?
  5. How would you know if someone has manipulated your memory?
  6. When Donald Duck gets out of the shower, why does he put on a towel when he normally doesn’t wear any pants?
  7. What have you forgotten today?
  8. Would it be acceptable to say that the opposite of progress is congress because the opposite of pro is con?
  9. Which of the two would you prefer to have as your roommate: A bird or an ostrich?
  10. Why do you think 11 isn’t pronounced only one?
  11. Why is it called “taking a dump”? Shouldn’t it be leaving a dump instead?
  12. Why can’t the professor on Gilligan’s Island fix a hole in a boat if he can construct a radio out of a coconut?
  13. Have you ever dropped food on the floor accidentally and then picked it up to eat it?
  14. What kind of tree would you be if you were one, and why?
  15. Do bald people still get dandruff?
  16. Are we really living or just slowly dying?
  17. Do you think a short person can “talk down” to a taller person?
  18. Why do you think is a boxing ring square?
  19. Have you ever had an extremely bad haircut?
  20. What is the least important thing that is very important to you right now?

241 Crazy Questions: list Continued.

  1. Is it weird to enjoy the smell of your own fart?
  2. What kind of noises did dinosaurs make?
  3. Where does your idea go when it has already been forgotten?
  4. How many times a day do you check yourself in front of the mirror?
  5. Is it possible to purchase a complete chess set at a pawnshop?
  6. Do the minutes on the movie boxes include previews, credits, and additional features, or are they just for the movie itself?
  7. What would you paint on your first day if you were an artist?
  8. How long do you think will you be remembered after the day that you die?
  9. Why do you have to “put your two cents in” when it is really only a “penny for your thoughts”? Where’s that extra penny going?
  10. Are you keeping a really huge secret from someone you love?
  11. Why does the sun make our hair lighter but make our skin darker?
  12. Do animals have the ability to commit suicide?
  13. Why do raindrops but snow falls?
  14. Have you ever peed while sleeping?
  15. Do you think you would be friends with a clone of yourself?
  16. When Greenland is white and ice-covered, why is it called Greenland?
  17. When did time actually begin?
  18. Why does wet hair turn darker despite the fact that the water is clear?
  19. Why does anything exist? In the beginning, there was totally nothing so how did something come from nothing?
  20. Which of the teachers would you prefer to have if you were a Hogwarts student?

241 Crazy Questions: Best Collection

  1. If we are clean before using bath towels then why do we need to wash them?
  2. Would you rather play in the sand or play in the water at the beach?
  3. What was the worst song that was ever composed?
  4. Which orange came first: the color or the fruit?
  5. Is it true that if you got into a cab and the driver drove backward, he owes you money?
  6. How would you be able to handcuff a one-armed man?
  7. Would you dare to take a lie detector test with a loved one asking the questions?
  8. Do you think you can daydream at night?
  9. Why isn’t there any mouse-flavored food for cats?
  10. Have you ever tried eating a piece of paper?
  11. Which day was a kid born if his leg came out at 11:59 p.m. but his head didn’t come out until 12:01 a.m.?
  12. You’ve recently joined the Spice Girls. What Spice name have you created for yourself?
  13. What do you think existed before the universe?
  14. You have a date with someone in this room tomorrow. Who would be the most unfit candidate?
  15. What was the weirdest text message you’ve ever got?
  16. Are the 10 calories in a pack of gum just for chewing the gum, or also for swallowing it?
  17. What’s the most boring sport to play and watch?
  18. Who actually decided what was right and wrong?
  19. Why do adults say they “slept like a baby” when babies wake up every few hours?
  20. Which one would you rather do: ask a question someone does not want to answer or give an answer someone does not want to hear it?

Surprise Your Buddies To Ask these 241 Crazy Questions

  1. Why do we enjoy Halloween if our parents tell us not to take candy from strangers?
  2. Do you think coffins have lifetime guarantees?
  3. When you can’t drink and drive, why do you need a driver’s license to buy alcohol?
  4. Can you describe the smell of your armpits?
  5. What are the things that would be much better if you could change its color?
  6. Is the Bible kept in the fiction or non-fiction section of libraries?
  7. Why don’t ghosts fall through the floor if they can walk through walls and glide downstairs?
  8. Which Disney princess do you think would make the best spy?
  9. What’s the purpose of setting goals if we’re all going to die in the end?
  10. Why can’t you just feel whelmed instead of overwhelmed and underwhelmed?
  11. Do fortune cookie predictions have a time limit?
  12. Which one would you rather do: sit in the snow while it is falling or dance in the rain?
  13. Do dentists consult with other dentists or do it on their own?
  14. What do you think is the ugliest part of your body?
  15. Does time flow forward only, or does it move differently also?
  16. What would happen to the sea level if every boat in the world was removed from the ocean at the same time?
  17. Who do you think taught the first teacher ever?
  18. SpongeBob’s parents are both rounds like sea sponges, but why is he square like a kitchen sponge?
  19. Would a bubble in space pop if you blew it?
  20. Do you believe there is something beyond what we can currently perceive in the universe?

Make Fun By Asking These 241 Crazy Questions

  1. Why does grape flavor smell like it when real grapes don’t taste or smell like it?
  2. How many kilograms of potatoes have you consumed throughout your life?
  3. How can pessimists motivate themselves to get out of bed every day?
  4. Why are they described as apartments when they are all connected?
  5. Rabbits don’t lay eggs, so why does the Easter bunny deliver them?
  6. Is it legal to drive down a road backward as long as you stay in the right lane?
  7. When was the last time you screamed your lungs out?
  8. Should fishermen consume the fish they catch, or should they simply release them?
  9. What sound would be the most horrifying if you could hear it?
  10. Why are we so terrified of making mistakes if we can learn from them and improve?
  11. Why is the Lone Ranger nicknamed “Lone” though he is constantly accompanied by his Indian friend Tonto?
  12. If an orange is the color orange, why isn’t a lemon called yellow or a lime called green?
  13. When doing first aid, have you ever purposefully hurt someone just enough to make them scream?
  14. Do you think prison buses have emergency exits?
  15. What is the longest time you have gone without showering?
  16. Why do you think is vanilla ice cream white when vanilla extract is brown?
  17. Are there belly buttons on Adam and Eve?
  18. If you’ll be expecting the unexpected, doesn’t that make the unexpected expected?
  19. Isn’t it strange that rearranging the word “teacher” gives “cheater”?
  20. Is it true that cannibals don’t like eating clowns because they taste crazy?

These 241 Crazy Questions Are Interesting

  1. How can a brain that is closed inside our skull ever be called an open mind?
  2. If you will be looking at a map of the inside of a planet, what would it look like?
  3. Why is your head sticking out from your t-shirt?
  4. Do you have crazy thoughts running through your head all day?
  5. Doctors call what they do practice, isn’t that a little unnerving?
  6. Cured ham was formerly infected with what disease?
  7. Why are the small candy bars referred to as “fun sizes”? Isn’t it more fun to consume the big one?
  8. We all know that milk goes bad if not refrigerated, but why doesn’t it go bad inside the cow?
  9. Which one would you rather have an arm that regenerates every week or legs that grows back in every week?
  10. How would anyone ever know if a word was misspelled in the dictionary?
  11. Why do green olives come in jars and black olives come in cans?
  12. When sheep brush against each other, do they get static cling?
  13. Have you ever been tempted to slap someone you’re talking to while you’re talking to them?
  14. When it involves the living body, why is it called plastic surgery?
  15. Did you fail or succeed if you were trying to fail and you succeeded?
  16. Why do banks charge money for insufficient balance, even when they know there isn’t any money?
  17. Do the FBI have to pay if they break down your door?
  18. Can you cry underwater?
  19. What language do people speak in their heads if they were born deaf?
  20. Is it possible for fish to be seasick?

241 Crazy Questions Mosty Liked By Youth

  1. When we can’t sleep, why do we count sheep but not dogs?
  2. Would you believe a person who told you they were a pathological liar?
  3. Why do 7-11 stores have locks on the doors if they are open 24 hours a day, 365 days a year?
  4. Is it required for atheists to swear on the Bible in court?
  5. What’s the weirdest job you’ve ever had?
  6. Where does it say that Humpty Dumpty is an egg in the nursery rhyme?
  7. Do stairs go up or go down?
  8. Is ketchup considered a smoothie since tomatoes are considered as fruits?
  9. If everyone says that life is totally unfair, doesn’t that just mean that life is fair?
  10. Would a vacuum form in your stomach if you farted and burped at the same time?
  11. What is a workstation if the train station is set to where the train is bound to stop?
  12. What lies beyond the limit if the sky is the limit?
  13. Is it still a dog pile when dogs climb on top of each other?
  14. How much wood do you think can a woodchuck chuck?
  15. Is there a synonym for synonym?
  16. When it comes to movies and concerts, do conjoin twins pay for one or two tickets?
  17. Is it true that if a child refuses to take a nap, it means they are resisting rest?
  18. Which one would you rather walk around with a salad on your head or broccoli on your arms?
  19. If corn oil is made from corn and vegetable oil is made from vegetables, where does baby oil come from?
  20. When someone with an accent thinks to themselves, do they have an accent in their thoughts, too?

Save This List of 241 Crazy Questions To Your Favourites

  1. If no one is supposed to step foot on the grass, then how did someone put the “keep off the grass” sign there in the first place?
  2. Why do you think isn’t bacon baked and cookies cooked?
  3. Do you become a hater if you despise haters? Will you despise yourself if you despise haters?
  4. Why is it that the glue doesn’t stick to the inside of the bottle?
  5. Why is it that your nose runs but your feet smell?
  6. What do you call a question with no answer?
  7. Did the sun shine first, or did the moon reflect it?
  8. Why is phonetic not spelled exactly as it sounds?
  9. Why aren’t curtains double-sided so that they look good both inside and outside your house?
  10. Why is hippopotomonstrosesquippedaliophobia such a long term if it means “a fear of long words?”
  11. Are individuals buried with their braces on?
  12. Why is Patience a virtue if early birds get the best advantages?
  13. Why do we kill people who kill people if killing people is wrong?
  14. How could the Wicked Witch of the West ever bathe if she melts in the water?
  15. Why do you think is it called a building when it is already built?
  16. Is it possible for monkeys to have a monkey’s uncle?
  17. Are the animals homeless because they don’t have a home?
  18. Can the word “dictionary” be found in the dictionary?
  19. Would the other doctors treat the doctor or the patient if a doctor suffered a heart attack while performing surgery?
  20. Why do we park on driveways and drive on parkways?

A Collection of 241 Crazy Questions

  1. Even when it’s delivered by plane or truck, why do we have to call it “shipping”?
  2. Do you yawn when sleeping?
  3. Are you a waiter yourself if you’re waiting for the waiter to take your order?
  4. When we like something, why do we put our hands together?
  5. Do you know the phrase “throw ya hands in the air like ya don’t care”? Why bother doing that if you don’t actually care?
  6. Who is right if two left-handed people had an argument?
  7. What do you think makes a question a question?
  8. Would a seahorse or a horse win a Miss Universe beauty pageant if animals had one?
  9. If Vampires cannot see their reflections, why is their hair always so tidy?
  10. Do glassblowers get a pane in their stomach if they inhale?
  11. How far does someone’s ownership of a piece of land go? Is it theirs all the way to the center of the Earth?
  12. When you die, do your eyes change color?
  13. Why is it said that you have a cold when your temperature rises?
  14. Why did we choose to make February only have 28 days while so many other months have 31? Couldn’t we have simply added some of the 31st days from other months to February?
  15. Will a teacher be “degraded” if they teach a younger grade than they previously taught?
  16. Is it possible for someone to be allergic to water?
  17. What time was the world created?
  18. Why do Germans live in Deutschland while Dutch people live in Holland?
  19. Is brushing your teeth possible without wobbling your bottom?
  20. We have always heard partly cloudy, but when do we actually start hearing partly sunny?
  21. When you plug something into an electrical socket, why is it called an outlet? Isn’t it supposed to be called an inlet?
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