1.How do you define success, at least for yourself? Have you reached it?
2. Is there anything you know you should let go of, but you haven’t yet? Why?
3. If you knew this was your last day, would you do the same things you’re doing?
4. What kind of legacy do you want to leave behind? What steps have you taken to create it?
5. If the person who’s hurt you the most showed up at your door, what would you say to them?
6. If you don’t have what you want, what do you have to lose by going after it?
7. What does it mean to be good with money? Are you?
8. Is there anything your job gives you besides money? Is there anything missing?
hardest questions to answer
9. What’s the biggest thing you want to accomplish in the next 12 months?
10. What responsibilities are you avoiding right now or which are you most tempted to avoid?
11. When it comes to your closest relationships, what do you struggle with the most?
12. What mistake do you keep making, and why do you keep making it? What has it cost you?
13. Name something you consider worse than dying. What makes it worse?
14. What’s something you wouldn’t want to die without doing? Why?
15. How would you define the word “American”? How do you define “unAmerican?”
16. If you had three wishes, what would you wish for, and why?
17. What fears are connected to your pursuit of success? How have you faced them?
18. What areas in your life are most in need of improvement?
19. How have your goals or priorities changed over the last decade?
20. What are your biggest regrets when you think over the past five years?
21. What realization has changed your life or your perspective over the past five years?
22. What is the biggest cause of stress for you right now? What worries you most?
23. Are you too hard on yourself or not hard enough?
24. What do you look forward to the most right now? Why?
25. What do you want to be remembered for when you die?
26. What dream (or dreams) have you given up on? Why?
27. What dream (or dreams) have you held onto the longest?
28. Is there anyone you’re jealous of? If so, why?
29. How are you contributing to the world? Or how do you want to contribute?
30. What is your default behavior when someone turns on you? What has it cost you?
31. When you look at the person you are right now, what are you proudest of?
32. What about yourself do you still need to work on every day? How do you work on it?
33. What have you learned that you might not have learned if you hadn’t suffered?
34. What five words would you use to describe yourself?
35. What would you do if fear wasn’t an issue and you couldn’t fail?
36. What would you give to not feel the way you feel right now?
37. If you could go back and delete an email before sending it, would you?
38. If you could change one thing about your government, what would it be?
39. Have you ever regretted publishing something? If so, why?
40. Do you put political stickers on your car? Why or why not?
41. When was the last time you did something outside your comfort zone?
42. What are you risking right now by not stepping outside your comfort zone?
43. Are there any relationships you’d like to improve or repair? Are any beyond help?
44. Have you alienated people only to regret having done so?
45. Do you forgive easily when someone apologizes for hurting or offending you?
46. Have you forgiven someone who refused to apologize for hurting you?
47. Has someone in your life died before you could reconcile with them (or they with you)?
48. Have you felt the need to pretend you don’t need help? If so, why?
49. When have you felt as though you could finally let someone take care of you?
50. Why do you think so many people grow up feeling the need to be “low maintenance”?
51. Have you felt this way yourself? And when have you gotten a break from it?
52. What are the most amazing things you’ve achieved this past three years?
53. What goal continues to elude you? What action are you taking to reach it?
54. What characteristics have you struggled to develop in yourself? (confidence? tenacity?
straightforwardness? courage? generosity?)
55. In what areas of your life and work do you feel most vulnerable? Why?
56. Do you make a point of expressing your gratitude and appreciation for others?
hardest questions to answer
57. Do you easily become frustrated or irritated when things don’t go your way?
58. Would it serve you well to trust people more than you do, or to be more careful of whom you
trust?
59. Do you think people ask too much of you — or too little? Why do you think they do?
60. When was the last time you had a good laugh? What was it about?
61. What do you most often choose to ignore? Why do you ignore it?
62. If someone were to follow you around for a week, would your values and priorities be obvious
to them? Would they match the ones you identify for yourself?
63. Have you ever abandoned a social media channel, not because of opposition to your views
but because that opposition came from family?
64. Have you ever experienced the same unkind treatment you dished out to someone else in the
past?
65. What is karma to you? Is it simply about justice, or do you see it as a deeply personal force
that teaches us what we need to learn?
66. What would you do if you only had one week or one month to live?
67. How can you make a lasting difference in the world?
68. How far are you willing to go to achieve your goals?
69. What has been the biggest lesson that life has taught you so far? And how have you applied
it in your situation?
70. How will you know when it’s time to let go of something that isn’t working for you?
71. What is your biggest fear regarding your loved ones?
72. How would you handle conflict between two opposing views?
73. Are there any problems too big for you to tackle? If so, which problems are these, and why
do you think they are too big for you?
74. What would you do if money wasn’t an issue
75. What do you struggle with the most when seeking happiness?
1. If you could master any skill instantly, what would it be?
2. What's the most fascinating documentary you've ever watched?
3. How do you define success?
4. If you could live in any historical era, which one would you choose and why?
5. What's your favorite piece of art, and why does it resonate with you?
6. If you could have dinner with any three people, dead or alive, who would they be?
7. What's the most unusual food you've ever tried, and did you like it?
8. How would you spend a million dollars if you had to spend it in a week?
9. If you could solve one major world problem, what would it be?
10. What’s your favorite book that you think everyone should read at least once?
11. How do you recharge when you're feeling drained?
12. If you could have any animal, real or mythical, as a pet, what would you choose?
13. What’s the most challenging thing you’ve ever done?
14. If you could change one thing about the education system, what would it be?
15. What historical event do you wish you could have witnessed firsthand?
16. What’s the most impressive thing you know how to do?
17. If you had to teach a class on one thing, what would you teach?
18. What’s your favorite quote, and why does it speak to you?
19. If you could travel anywhere in the world for free, where would you go and why?
20. What hobby would you get into if time and money weren’t an issue?
21. What's your most treasured memory?
22. If you could switch lives with someone for a day, who would it be?
23. What’s a belief you hold that many people disagree with?
24. What’s the best piece of advice you’ve ever received?
25. If you had to eat one meal for the rest of your life, what would it be?
26. What’s your biggest fear, and how do you try to overcome it?
27. What is something you’ve never done but would like to try?
28. If you could instantly learn any language, which one would you choose?
29. What’s the most inspiring place you’ve ever visited?
30. How do you handle failure or setbacks?
31. What do you think is the most underrated virtue?
32. If you could have any job for a day, what would it be?
33. What’s the strangest thing you’ve ever experienced?
34. What’s your favorite way to spend a weekend?
35. If you could invent something, what would it be?
36. What’s the best movie you’ve seen recently, and what did you like about it?
37. How do you stay motivated during difficult times?
38. If you could witness any event in the future, what would you want to see?
39. What’s your favorite way to give back to the community?
40. If you could redesign the human body, what improvements would you make?
41. What’s the most important lesson you’ve learned in the past year?
42. If you could live in any fictional world, which one would it be and why?
43. What’s something you’re proud of that not many people know about?
44. How do you define true happiness?
45. What’s a skill you think everyone should learn?
46. What’s the most interesting fact you know?
47. If you could have any superpower, but it could only be used for mundane tasks, what would it
be?
48. What’s the best compliment you’ve ever received?
49. How do you approach making difficult decisions?
50. What’s a tradition from your culture that you value the most?
movie.
1. What is the title of your favorite movie, and who directed it?
2. Why did you choose this movie as your favorite?
3. Can you summarize the plot of the movie?
4. Who are the main characters, and which actors play them?
5. What genre does this movie belong to?
6. What themes are explored in the movie?
7. What was the most memorable scene or moment in the film?
8. How does the movie's setting contribute to the overall story?
9. What message or lesson did you take away from the movie?
10. How does the soundtrack enhance the movie's atmosphere?
11. What are some interesting facts or trivia about the production of the movie?
12. How was the movie received by critics and audiences when it was released?
13. Did the movie win any awards or receive any notable nominations?
14. What is your favorite line or quote from the movie, and why?
15. How do the cinematography and visual effects contribute to the movie's impact?
16. What emotions did the movie evoke in you, and why?
17. How does the movie compare to others in the same genre?
18. If the movie is based on a book or true story, how faithful is it to the source material?
19. What aspects of the movie could have been improved or done differently?
20. Would you recommend this movie to others? Why or why not?
21. How do the costumes and production design add to the authenticity of the movie?
22. What role does the director play in the success of the movie?
23. How do the supporting characters contribute to the overall story?
24. What are some recurring motifs or symbols in the movie?
25. How does the movie's pacing affect the storytelling?
26. What is the significance of the movie's title?
27. How does the movie handle character development and arcs?
28. What was the budget for the movie, and how does it reflect in the production quality?
29. How did the movie impact popular culture or influence other films?
30. What social or political issues does the movie address, if any?
31. How does the dialogue in the movie enhance the narrative?
32. What role does the director's style play in the movie's presentation?
33. How does the movie's opening scene set the tone for the rest of the film?
34. What challenges did the filmmakers face during production?
35. How does the ending of the movie leave a lasting impression on the audience?
36. What are some memorable quotes or dialogues from the movie?
37. How does the character's journey or transformation drive the plot?
38. What was the audience's reaction to the movie when it was first released?
39. How do the special effects hold up over time?
40. What makes this movie stand out from others released in the same year?
41. How does the movie balance entertainment and deeper meaning?
42. What role does music play in key scenes of the movie?
43. How does the movie address universal themes that resonate with many viewers?
44. What inspired the filmmakers to create this movie?
45. How does the narrative structure (e.g., linear, non-linear) affect the storytelling?
46. What aspects of the movie have influenced your personal taste in films?
47. How do the character relationships drive the plot forward?
48. What life lessons or morals can be learned from the movie?
49. How do the movie's visual style and color palette enhance the story?
50. How does the movie's marketing and promotion affect its popularity and reception?
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