Hard Questions to Ask Your Friends (2022)

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Hard Questions to Ask Your Friends. Regardless matter how long you’ve known someone, it’s critical to keep working on deepening & strengthening your bond with them. Although there are numerous ways to accomplish this, giving intimate details about our feelings and thoughts is one of the best.

By asking the appropriate questions, you can start conversations with your friends that will allow users to connect more deeply and really get to know them on a more intimate level. These are excellent discussion starters for times when you have the opportunity to slow down, connect, and be present with one another. This might be over coffee or while taking a stroll outside.

We also included some fun and hard questions at the end because getting to know your friends doesn’t always have to be so serious. They’ll put your pals’ wits to the test in a fun and unique way.

Hard Questions to Ask Your Friends

Asking questions is the best method to get to know your friends better. The more personal, in general, the better. Although these difficult questions can be difficult to answer and can be intimidating to ask, discussing the answers with each other can assist to strengthen your bond.

  1. What do you think is the meaning of life?
  2. What is the best part about being you?
  3. Are there any conversation topics that make you feel uncomfortable?
  4. What’s your favourite childhood memory?
  5. Would you rather be able to talk to animals or speak every language?
  6. What is your worst fear?
  7. Where do you see yourself in 5 years?
  8. In what ways do you self-sabotage?
  9. Are there any hard truths that you’re afraid to admit to yourself?
  10. Would you rather find your soulmate or your life purpose?
  11. Do you feel deserving of love?
  12. What was the saddest day of your life?
  13. Is there anything about yourself that you really wish you could change?
  14. What do you love most about yourself?
  15. What is your life brings you the most happiness?
  16. What do you consider your worst habit?
  17. Do you think that good things come from suffering?
  18. If you knew you were going to die tomorrow, how would you spend today?
  19. Is there anything that you’ve done that you still feel guilty about to this day?
  20. What is the most challenging thing you’re dealing with in your life right now?
  21. If you could trade places with someone for a day, who would you choose?
  22. What is something that you used to believe in but don’t anymore? And what changed?
  23. Do you think there is a difference between living and existing?
  24. If you had a friend that spoke to you the same way you spoke to yourself, would you be friends with them?
  25. What makes you feel free?
  26. Who in your life has been the most difficult to say goodbye to?
  27. Do you think your parents did a good job raising you?

Hard questions to ask your friends about yourself

How well do you believe your friends and best friend know you? By asking your friends the following questions about yourself, you can gain a better understanding of how they perceive you and your friendship.

  1. What is my worst fear?
  2. What do you think is my worst habit?
  3. What do you admire most about me?
  4. In what ways do you think I keep myself stuck?
  5. What do you think is my biggest strength?
  6. How do you describe me to people that don’t know me?
  7. What do you think is the most important thing in my life?
  8. What makes me feel stressed?
  9. Who are the most important people in my life?
  10. Do I consider myself a perfectionist? Do you think this has a negative impact on me?
  11. What motivates me to work hard?
  12. What accomplishment do you think I’m the proudest of?
  13. What do you think would be a perfect career for me?
  14. Do you consider me to be a negative person?
  15. How do you think I would spend my perfect day?
  16. What is one unique quality about me that you love?
  17. How would you describe me in 3 words?
  18. What major do you think I will choose, and why?
  19. What is standing in the way of me being successful?
  20. What is something about me that you think only you know?
  21. What has been the hardest thing I’ve had to deal with in my life?

Hard questions to ask your best friend

We may feel as if we’ve asked all the questions there are to ask about our best friends, but there is always more to learn about them, no matter how long we’ve known them.

  1. Are you happy?
  2. Do you feel beautiful?
  3. Do you feel fulfilled?
  4. What do you admire most about yourself?
  5. Do you think we will always be best friends?
  6. How can I be a better friend to you?
  7. Do you know what your purpose is? Are you working to live on purpose?
  8. How often do you find yourself missing your ex?
  9. Would you rather marry for love or money?
  10. When was the last time you felt deeply inspired, and why?
  11. Would you trust me with your life?
  12. Do you feel like there are a lot of things that you worry about?
  13. Is there anything right now that you know you should be doing, but are afraid to do?
  14. What does your dream life look like?
  15. Do you think it’s possible to learn hard lessons without making mistakes?
  16. What was an experience recently where you felt let down by me?
  17. Is there something that you feel as though you’re lacking in your life?
  18. What does the perfect relationship look like to you?
  19. What is one thing you’d be doing right now if you had no fear of being judged?
  20. What areas of your life would you like to grow in, and how can I help support that growth?

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