182 Hardest Questions To Answer And Ask Someone

Did you ever think about the hardest questions to answer and ask someone? I’ve compiled a list of brain teasers for you.

These are great questions to ask your friends and discuss the answers together. You’ll also find some interesting trivia and quiz questions, as well as a list of funny questions that will make all of you laugh.

Now, don’t let me keep you. Enjoy this list of the hardest questions to answer and don’t worry too much if you don’t have an answer because, after all, they’re the toughest ones in the world.

Hardest Questions To Answer About Yourself

1. What if you didn’t exist?

2. Do you feel stuck?

3. If the person who’s hurt you the most showed up at your door, what would you say to them?

4. What’s your biggest regret? Did you learn from it, and how has your mindset on it changed since then?

5. If you could travel back in time to the day you were born, what would you do differently?

6. What mistake do you keep making, and why do you keep making it? What has it cost you?

7. Could you just be existing in a dream that your eight-year-old self is dreaming? How would you ever know?

8. What do you have to do to make your life complete?

9. How are you contributing to the world? Or how do you want to contribute?

10. Would you rather spend all day cleaning someone’s house, or let your crush clean yours?

11. Do you feel like you’re on a merry-go-round?

12. What is your default behavior when someone turns on you? Has it ever cost you something? If so, what?

13. What is the easiest way to get to your heart?

14. Are you living for the future or the past?

15. Would it serve you well to trust people more than you do, or to be more careful of whom you trust?

16. Do you feel like you’ve lived this same day many times before?

17. Have you ever found yourself in the wrong place at the right time?

18. What would you do if fear was not a factor and you could not fail?

19. Are you the person you want to be?

20. Is there anything you know you should let go of, but haven’t yet? Why?

21. Have you ever been in a dream in your life?

22. If you don’t have what you want, what do you have to lose?

23. If you knew this was your last day, would you do what you’re doing now?

24. Have you ever been on a journey that you didn’t know what it was about?

25. Have you ever experienced the same unkind treatment you dished out to someone else in the past?

26. If life is short, why do you dwell on things that don’t matter?

Hardest Question About Life

1. What is the meaning of life?

2. Does money really buy happiness?

3. What is karma to you? Is it simply about justice, or do you see it as a deep personal force that teaches us what we need to learn?

4. Why is letting go so hard? For all of us who were struggling with letting go of someone, this is a very, veryyy tough question to answer.

5. Do you think there’s a difference between living and existing?

6. What matters?

7. Are we living, or are we dying?

8. Is there really a Santa Claus?

9. Can love really last a lifetime?

10. Why do the people who show off more than they do or live a self-oriented life shine more than the ones who are working with their heads down, bringing a real difference to people’s lives?

11. Where do we go when we die?

12. Why do married folks begin to look like one another?

13. Overall, are we, humans, getting more tolerant, or are we becoming more rigid?

14. Name something you consider worse than death. What makes it worse?

15. Why does summer zoom by and winter drag on forever?

16. Do the problems of a human evolve or do we keep thinking about the same things?

Hard Questions To Answer

1. How would you define the word “American”? How do you define “unAmerican?”

2. Who decided what’s right and what’s wrong?

3. Which came first: the sun or the earth?

4. What if time wasn’t linear? How can we always be advancing forward?

5. Do you ever really do anything out of your own conscious choice, or are we always controlled by some external stimulation or motive?

6. At what time did time begin?

7. If the sky’s the limit, then what is space?

8. Did you arrive at this point in your life because you wanted to or because you were destined to be here?

9. Is the opposite of the opposite the same or opposite?

10. Why is a pizza box square when a pizza is round?

11. Is there an end to the universe, or does it just keep going?

12. Did humans invent math or discover math?

13. If life were a video game, what would some of the cheat codes be?

14. Which orange came first – the fruit or the color?

15. If God invented humans, who created God?

16. Is it really possible to experience anything objectively?

17. Why do we make exceptions to rules if we all should follow the rules?

18. What are dreams?

19. How can you describe something indescribable?

Hardest Interview Questions

1. What are your weaknesses?

2. What can you do for us that someone else can’t?

3. Describe a situation where you have gone above and beyond?

4. In your present (last) position, what problems did you identify that had previously been overlooked?

5. What critical feedback do you most often receive?

6. Describe a situation where you have had others follow your lead?

7. Is there a gap in your resume? If so, what is it?

8. Have you ever had to fire people? What were the reasons, and how did you handle the situation?

9. What attributes do you have that will support you in this role?

10. Describe yourself in three words.

11. Did you think of leaving your present position before? If so, what do you think held you there?

12. How long would it take you to make a meaningful contribution to our firm?

13. What does the ideal work day look like to you?

14. Can you work under pressure and deal with deadlines?

Hardest Questions To Answer Funny Edition

1. Where do the missing socks go?

2. What are two things you can never eat for breakfast? (Lunch and Dinner) – this is a very tricky and fun question to ask your friends.

3. Are child actors in adult-rated movies allowed to watch the film?

4. If you were a fruit or vegetable, what would you be and why?

5. If you hate haters, does that make you a hater and will you hate yourself?

6. How far east can you travel before you are traveling west?

7. What is white and black, but red all over? (A newspaper)

8. What body part would you like to add?

9. If you spell “sit in the tub” s-o-a-k, and you spell “a funny story” j-o-k-e, how do you spell “the white of an egg”?

10. Does a staircase go up or down?

11. Do cannibals think clowns taste funny?

12. If you were a flavor of ice cream, what would you be and why?

13. How many chickens would it take to kill an elephant? This one will forever be the funniest question for me.

14. What came first: the seed or the plant?

15. What gets wetter the more it dries?

16. If you are bald, can you get dandruff?

17. Where did the name Pina Colada come from?

18. Why does the Easter Bunny bring eggs when rabbits don’t lay eggs?

Toughest Trivia Questions

1. Do animals really have a sixth sense?

2. When you forget a thought, where does it go? This is a very good question that, unfortunately, I’m not able to give an answer to.

3. What two planets in our solar system have no moons?

4. In which sport are barani, rudolph, and randolph all techniques?

5. Which European country technically shares a border with Brazil, because one of its “overseas departments” does?

6. Which film became the first to be directed by a woman to earn more than $100 million at the U.S. box office?

7. What can happen if a star passes too close to a black hole?

8. Hamilton Kindley Field International Airport is in which country?

9. Who was murdered along with OJ Simpson’s estranged wife, Nicole?

10. What “finger-lickin’ good” company piloted a chicken-flavored nail polish?

11. What is the world’s oldest known musical instrument authentically made from bird bone and mammoth ivory?

12. What is the highest mountain ever discovered?

13. The ‘girl in the polkadot dress’ was an eyewitness to whose assassination?

14. In printing, it’s the color black. In chemistry, it’s potassium. In baseball, it’s a strikeout. Which letter is it?

15. Name the well-known island country known for its three Rs: reggae, romance, and running.

16. What celestial object was identified as being a spiral?

17. A “crepuscular” animal becomes active at what time?

18. Samuel Tilden, Grover Cleveland, Al Gore, and Hillary Clinton share what distinction among U.S. presidential candidates?

19. What is the name of the British archaeologist who discovered Tutankhamun’s tomb?

20. How much more in weight does the sun weigh than Earth?

21. If you order “murgh” from the menu at an Indian restaurant, what meat will you get?

22. What Scottish poet’s works inspired the book titles Of Mice and Men and Catcher in the Rye?

23. Where can you find the traditionally Juniper-flavored beer called Sahti?

24. Someone weighing 220lbs on Earth would weigh about how much on Mars?

25. Kersti Kaljulaid was 46 years old when she became the youngest president ever elected to lead which country?

26. What Indian mausoleum was called a “teardrop… on the cheek of time” by Nobel Prize in Literature Laureate Rabindranath Tagore?

Hard This-Or-That Questions

1. Instagram or Facebook?

2. Predictability or excitement?

3. Save 100 strangers or one loved one?

4. Poor and happy or rich and miserable?

5. Ability to travel without a passport or ability to read minds?

6. Intense pain for ten minutes or dull pain for one day?

7. New phone or a new laptop?

8. Cherished or respected?

9. See the future or change the past?

10. Underestimated or overestimated?

11. Stop using paper or stop using plastic?

12. False hope or unnecessary anxiety?

13. Work or school?

14. Misunderstood after death or forgotten after death?

15. Time machine or magic wand?

16. Second chance at love or second chance for your career?

17. Love or money?

18. Massive success by accident or modest success on purpose?

19. Logic or emotion?

Tough Would-You-Rather Questions

1. Would you rather get a paper cut between your fingers every time you touch paper or bite your tongue every time you eat something?

2. Would you rather smell like rotten eggs when you burp or have a green cloud appear every time you farted?

3. What would you rather have an arm that regenerates every month, or legs that grow back every month?

4. Would you rather give up social media or eat the same dinner for the rest of your life?

5. Would you rather be able to detect any lie you hear or get away with any lie you tell?

6. Would you rather be half your height or double your weight?

7. Would you rather share a toothbrush with a random stranger or kiss a random stranger on the mouth?

8. Would you rather live with a barnyard of animals in your house or live in the barn with the animals?

9. Would you rather never hear music again or lose the ability to read?

10. Would you rather have hiccups for the rest of your life or constantly feel like you have to sneeze without being able to?

11. What would you rather have to deal with: Have no nose, but have really good-smelling fingers? Or be blind but have a really nice smile?

12. Would you rather chew your toenails off or someone else’s fingernails?

13. Would you rather walk around with a salad for a head or broccoli for your arms?

14. Would you rather have hair that grows really fast and long, or have the same length of hair for the rest of your life?

15. Would you rather have no one come to your wedding or your funeral?

16. Would you rather be able to conjure up anything you want at any time but have a scar appear on your face every time you do? Or have one non-money-related wish granted once every five years with no punishment?

17. Would you rather get rich in a way that disappoints your family or just make enough money to live?

18. Would you rather have sex with a goat and no one would know or not have sex with a goat but everyone believes you did?

19. Would you rather go back in time to meet your ancestors or go into the future to meet your great-grandchildren?

20. Would you rather have to go to jail for a year or live in your car for a year?

21. Would you rather be able to read everyone’s minds all the time with no ability to turn it off or forget everything important about each person who’s closest to you?

22. Would you rather live in a mountain cabin with no human contact or a big city studio apartment with no personal space?

23. Would you rather lose social media or three of your close friends for the rest of your life?

24. Would you rather have your dream job for only two years or never have your dream job but be paid generously in a job you hate?

25. Would you rather read your mother’s teenage diary or read your teenage diary to your mother?

26. Would you rather be blind for the rest of your life or deaf and mute for the rest of your life?

27. Would you rather feel intense pain every time someone said your name or never be able to know when a person was talking to you?

Challenging Trick Questions To Ask Someone

1. What if everyone was actually colorblind? How would we know if we weren’t? If we all are, does that mean no one is?

2. If a plane crashes on the border between the United States and Canada, where do they bury the survivors?

3. Why does the moon appear in the daytime?

4. What is always coming but never arrives?

5. How can you lift an elephant with one hand?

6. What word is spelled incorrectly in every single dictionary?

7. If the vice president were to die, who is supposed to be president?

8. Why is it against the law for a man living in North Carolina to be buried in South Carolina?

9. What do an island and the letter “t” have in common?

10. How many books can you put in an empty backpack?

11. What has a head, and a tail, but does not have a body?

12. What starts with “e” and ends with “e” but only has one letter in it?

13. Can you name the two days starting with T besides Tuesday and Thursday?

14. What can you hold without touching it at all?

15. How do you make number one disappear?

16. What happened when the wheel was invented?

17. What is it that if you have it, you want to share it with me, and if you share it, you do not have it?

Final Words

Do you agree that these are the hardest questions to answer? Did you manage to answer any of them or did you find them difficult to answer?

Though, you have to admit that they’re still very interesting. Most of them are philosophical questions and they really give you something to think about.

You can share them on your social media or you can ask your friends or co-workers and see what their answers are. Now, I’ll leave you thinking about these toughest questions of all times. Have fun!