Do you think you and your friend know everything about each other? Asking tough questions and sharing our deepest thoughts is how we form strong bonds of true friendships. And if you’ve never brought up tricky topics with your friend and don’t know where to start, just begin with simple inquiries.
And when you’re ready to take your friendship to new heights, these hard questions to ask your friends about yourself will get you both to open up. But tread carefully; you don’t want the answers to burn any bridges.
140 Hard Questions To Ask Your Friends About Yourself
#1. Do you trust me?
#2. What are the most irritating characteristics I possess?
#3. Do I usually compete with others a lot?
#4. Which season is my favorite?
#5. Which word best describes me?
#6. Do your parents like me?
#7. What is the most daring thing I’ve ever attempted?
#8. Describe me in three words.
#9. Was there ever a moment when you felt our friendship would end?
#10. What is my most annoying trait?
#11. What is my most memorable life experience?
#12. How important do you think we are in each other’s life?
#13. What do you think will make our friendship stronger?
#14. What’s the most embarrassing thing that has ever happened to me?
#15. Which gift has been the most memorable for me?
#16. Where do you see me in five years?
#17. Do I have a hidden talent that no one else is aware of?
#18. What quality of mine should I change?
#19. Which book is my favorite?
#20. Do you think I have ever stolen anything?
#21. What are my regrets?
#22. Do you consider me optimistic or pessimistic?
#23. What fashion trend do you want me to give up?
#24. Which destination would I choose for a vacation?
#25. What’s my love language?
#26. Am I a reasonable person?
#27. Have I ever been bullied?
#28. What do you think will happen to me when I die?
#29. What is my favorite memory from our time together?
#30. What irritates me the most?
#31. Have you ever been disappointed in me?
#32. Do you think I lie? What would be the last lie I told?
#33. Do you believe that honesty makes friendships stronger?
#34. Do you see me as a miser or a generous person?
#35. Am I holding on to something I need to let go of?
#36. When did I last push the boundaries of my comfort zone?
#37. Does our friendship qualify as genuine friendship?
#38. What is my greatest fear?
#39. What is the one thing guaranteed to put me in a good mood?
#40. How long did it take you to trust me?
#41. If you had to move away, would you remain friends with me?
#42. What makes our friendship special?
#43. What matters the most to me?
#44. Do you think I am being true to myself?
#45. Do I take you for granted?
#46. Do you regret knowing me?
#47. Am I putting enough effort into our friendship?
#48. If I could change my profession, what would I choose?
#49. What are your favorite memories about us?
#50. If your partner told you to quit being friends with me, would you?
#51. Do you judge me when something goes wrong, or do you think of ways to help?
#52. What is the one unique quality I have that you admire?
#53. Is there anything you would like me to change about myself?
#54. Have I ever shown you some form of kindness that you’ll remember for life?
#55. Do you think I am taking care of myself physically?
#56. Am I using my time wisely?
#57. Have I done anything lately that’s worth remembering?
#58. What’s the one thing you’d always remember me by?
#59. Would you call me a religious person?
#60. Do you think I would steal to feed a starving child?
#61. What was I like in high school? Describe me in five words; no explanation is needed.
#62. Do you think I make sensible decisions?
#63. Are you proud that I am your friend?
#64. Can you 100% rely on me through thick and thin?
#65. Do you trust me with your life?
#66. Was (a particular situation) my fault?
#67. Would you want me to be your roommate?
#68. Whom do I admire the most?
#69. Were there times when you were doubtful of me?
#70. Where do you think my life is headed?
#71. What’s my weakness?
#72. Do I handle stress well?
#73. Do I handle disappointment well?
#74. Do I tend to gloat?
#75. Have I ever bullied you before?
#76. How different am I now from 5 years ago?
#77. Do you think I’ll succeed in being a [specific profession]?
#78. If I die next week, what will you say during my eulogy?
#79. What do you think is my primary coping strategy?
#80. Do you think I go for specific types of guys/girls? Is it a good thing or a bad thing?
#81. Am I too trusting/naive?
#82. Are there any toxic, extremely negative people in my life?
#83. On a scale of 1-10, how optimal is my self-care?
#84. Are there any conversation topics that make you feel uncomfortable?
#85. What is my ideal definition of success?
#86. What is the single, most significant change I can make this year?
#87. Do I remain a victim of an experience or belief I’ve been unwilling to let go of?
#88. What enjoyable activity do I need to engage in more often (or at all)?
#89. Do I acknowledge and celebrate my wins, even the smaller ones?
#90. Do I quickly get frustrated or angry with people who don’t do things the way I do them?
#91. Do you think I’m capable of asking for (and, in some cases, providing) the support I need?
#92. Do I carefully consider other people’s suggestions before I dismiss them?
#93. Have I ever acted petty?
#94. Do I self-sabotage?
#95. What would be my top three wishes if I had a realistic magic wand?
#96. After my many heartbreaks, do you think I’ll find my life partner?
#97. Am I easy to anger?
#98. When was the last time I had a good laugh?
#99. Do you think I am stuck where I’m at now?
#100. What do I most often choose to ignore?
#101. What are my top three values, and how do they apply to my business?
#102. Do you think I am happy?
#103. Am I living my passion?
#104. Can I be a better listener?
#105. Do you think I am successful?
#106. Do you think I am a failure?
#107. Do I say yes/no too much?
#108. Am I living for the future or the past?
#109. Do I verbally praise and thank the people who support me?
#110. Do you think I am a good person?
#111. Do you think I feel fulfilled?
#112. Do you think we will always be friends?
#113. Why did you choose me to be your friend?
#114. Do you consider me to be a negative person?
#115. What is my worst habit?
#116. What motivates me to work hard?
#117. What was your first impression of me?
#118. What do you think is my biggest strength?
#119. If I won the lottery, what would I do with the money?
#120. What is the one thing I’d like to change from my childhood?
#121. How do you describe me to people that don’t know me?
#122. Do you think I consider myself a perfectionist? Does this have a negative impact on me?
#123. Do you think I’ll marry for love?
#124. What is something about me that you think only you know?
#125. What was the first thing you noticed when you first met me?
#126. What accomplishment am I the proudest of?
#127. What would be a perfect career for me?
#128. If I had to fight for one global cause for the rest of my life, what would it be?
#129. What has been the hardest thing I’ve had to deal with?
#130. Is it easy to make me laugh?
#131. Can you count on me to tell you both good and bad news?
#132. What should be my spirit animal?
#133. Am I an introvert or an extrovert?
#134. Why do you think people misunderstand me?
#135. Do I make decisions with my head or with my heart?
#136. Am I saved in of your speed dial contacts?
#137. Do I share too much on social media?
#138. Do I need to join a dating app?
#139. Would you trade one day to be me?
#140. What animal best represents me?
