100 Hard and Tricky Questions to Ask Your Friends

Regardless of how long you’ve known someone, it is important to always continue working on deepening and strengthening your connection with them. Although there are many ways to do this, sharing intimate details about our thoughts and feelings is a great way to do so.

By asking your friends the right questions, you can create conversations that will allow you to connect more deeply and get to know your friends on a more intimate level.

These questions are great conversation starters for occasions where you have the opportunity to slow down, connect and be present with each other. This could be over coffee or while going for a nice walk outdoors.

And because getting to know your friends doesn’t always have to be so serious, we added some fun and tricky questions at the end. They will test your friends’ wittiness in a fun and creative way.

Sections

  1. 22 best hard questions to ask your friends
  2. Hard questions to ask your best friend
  3. Hard questions to ask your friends about yourself
  4. Trick questions and riddles to ask your friends
  5. Confusing questions to ask your friends
  6. Hard math questions to ask your friends

Best hard questions to ask your friends

The best way to get to know your friends better is to ask them questions. In general, the more personal, the better. Although these hard questions might be tough to answer and feel a little scary to ask, sharing the answers with each other will help to deepen your connection.

1. Would you rather be able to talk to animals or speak every language?
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2. What is your worst fear?
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3. Where do you see yourself in 5 years?

4. Are there any conversation topics that make you feel uncomfortable?
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5. What’s your favorite childhood memory?
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6. In what ways do you self-sabotage?

7. Are there any hard truths that you’re afraid to admit to yourself?
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8. Do you feel deserving of love?
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9. What is something that you used to believe in but don’t anymore? And what changed?

10. Would you rather find your soulmate or your life purpose?
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11. If you could trade places with someone for a day, who would you choose?
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12. What was the saddest day of your life?

13. What is the most challenging thing you’re dealing with in your life right now?
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14. Is there anything about yourself that you really wish you could change?
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15. What do you love most about yourself?

16. What in your life brings you the most happiness?
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17. If you knew you were going to die tomorrow, how would you spend today?
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18. What do you think is the meaning of life?

19. Is there anything that you’ve done that you still feel guilty about to this day?
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20. What do you consider your worst habit?
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21. Do you think that good things come from suffering?

22. What is the best part about being you?

Here is a list with more deep questions to ask your friends.

Hard questions to ask your best friend

With our best friends, it can sometimes feel like we’ve asked all the questions there are to ask, but there is always more that we can learn about our bestie, regardless of how long we’ve known them.

1. Do you think we will always be best friends?
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2. Do you think it’s possible to learn hard lessons without making mistakes?
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3. What was an experience recently where you felt let down by me?

4. What do you admire most about yourself?
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5. Do you know what your purpose is? Are you working to live on purpose?
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6. How often do you find yourself missing your ex?

7. Do you feel beautiful?
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8. When was the last time you felt deeply inspired, and why?
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9. Would you trust me with your life?

10. Do you feel like there are a lot of things that you worry about?
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11. Is there anything right now that you know you should be doing, but are afraid to do?
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12. What does your dream life look like?

13. Are you happy?
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14. What areas of your life would you like to grow in, and how can I help support that growth?
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15. Do you feel fulfilled?

16. How can I be a better friend to you?
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17. Is there something that you feel as though you’re lacking in your life?
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18. What does the perfect relationship look like to you?

19. Would you rather marry for love or money?
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20. What is one thing you’d be doing right now if you had no fear of being judged?
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21. Do you think there is a difference between living and existing?

22. If you had a friend that spoke to you the same way you spoke to yourself, would you be friends with them?
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23. What makes you feel free?
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24. Who in your life has been the most difficult to say goodbye to?

25. Do you think your parents did a good job raising you?

If you want to get closer with your bestie, go here for more questions to ask your best friend.

Hard questions to ask your friends about yourself

How well do you think your friends or your best friend knows you? Asking your friends the following questions about yourself will allow you to better understand how they feel about you and your friendship.

1. What do you think is my worst habit?
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2. What do you admire most about me?
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3. In what ways do you think I keep myself stuck?

4. What do you think is my biggest strength?
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5. How do you describe me to people that don’t know me?
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6. What do you think is the most important thing in my life?

7. What makes me feel stressed?
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8. Who are the most important people in my life?
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9. Do I consider myself a perfectionist? Do you think this has a negative impact on me?

10. What motivates me to work hard?
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11. What accomplishment do you think I’m the proudest of?
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12. What do you think would be a perfect career for me?

13. Do you consider me to be a negative person?
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14. How do you think I would spend my perfect day?
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15. What is one unique quality about me that you love?

16. How would you describe me in 3 words?
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17. Where do you see me in 5 years?
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18. What is my worst fear?

19. What has been the hardest thing I’ve had to deal with in my life?
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20. What major do you think I will choose, and why?
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21. What is something about me that you think only you know?

22. What is standing in the way of me being successful?

Trick questions and riddles to ask your friends

Looking for some questions to stump your friends? Then you’ve come to the right place. Enjoy asking your friend these challenging yet funny questions.

Trick questions to ask your friends

If you want to have fun testing your friends and seeing how quick they are on their toes then these are the perfect questions for you.

1. Is it legal for a man to marry his widow’s sister? (The man is dead, that’s why his wife is a widow)
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2. If a plane crashes on the border between Canada and America where do you bury the survivors? (Why would you want to bury survivors?)
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3. If you have a bowl with six apples and you take four, how many would you have? (You just took four, so you would have four)

4. If Mrs. Johnson’s bungalow was decorated completely in pink, with pink floors, pink furniture, pink walls, what color would the stairs be? (It’s a bungalow so there are no stairs)
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5. How did a boy kick a soccer ball 10ft. and then have it come right back to him? (He kicked it up into the air)
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6. What do you call a woman who knows where her husband is all the time? (A widow)

7. What do you throw out when you’re using it and keep close when you’re not? (An anchor)
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8. What can be broken but never held? (A promise)
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9. What lives when it is fed but dies when it drinks? (A fire)

10. When do you stop at green and go at red? (When you’re eating a watermelon)

Hard riddles to ask your friends

The following questions are challenging to answer but will definitely be fun to ask! Keep your friends on their toes with these 8 riddles for your friends.

1. I like to twirl my body but keep my head up high. After I go in, everything becomes tight. What am I? (A screw)
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2. I can fly but have no wings. I can cry, but I have no eyes. Wherever I go, darkness follows me. What am I? (A cloud)
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3. Although I may have eyes, I cannot see. I have a round brown face with lots of acne. What am I? (A potato)

4. I am lighter than air, but a hundred people cannot lift me. Careful, I am fragile. What am I? (A bubble)
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5. What bank has no money? (A blood bank)
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6. What can fly without wings? (Time)

7. What has thirteen hearts but no organs? (A deck of cards)
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8. What can run but not walk? (A river)

Confusing questions to ask your friends

These questions are deep and definitely on the confusing side. There is a good chance that asking the following 9 questions will lead to an interesting and possibly unexpected conversation, so be ready.

1. If a tree falls in the forest, does it make a sound?
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2. Are children who act in R-rated films allowed to attend the premiere?
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3. If you’re shorter than someone, is it possible to talk down to them?

4. Where does a thought go when it’s forgotten?
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5. Do Siamese twins pay for one or two tickets?
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6. How do you know that we’re not really living in the matrix?

7. Is it possible to put on mascara without raising your eyebrows?
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8. If a psychic can predict the future, why are they not always winning the lottery?
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9. If a surgeon had a heart attack during an operation, would the other staff save the doctor or the patient?

Hard math questions to ask your friends

Most of these questions are meant for second graders, but that doesn’t mean that they’re easy to answer. School your friends with the following surprisingly tough math questions.

1. Sally is 54 years old, and her mother is 80. How many years ago was Sally’s mother 3 times her age? (41 years ago, when Sally was 13 and her mom was 39)
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2. There is a 3-digit number. The second digit is 4 times as big as the first digit, while the first digit is 3 less than the second digit. What is the number? (141)
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3. There were some people on a train. 19 people got off the train at the first stop, and 17 people got on the train. Now there are 63 people on the train. How many people were on the train in the first place? (65)

4. An orchestra of 120 players takes 40 minutes to play Beethoven’s 9th symphony. How long would it take 60 players to play the same symphony? (Same amount of time)

Viktor is a Counselor specialized in interpersonal communication and relationships. He manages Socialpro’s scientific review board. Follow on Twitter or read more.

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