107 Deep Questions to Ask Your Friends (And Connect Deeply)

Asking your friends deep or philosophical questions can kickstart interesting and enlightening conversations. Deep questions can help you both learn more about yourself, the other person, and the world.

Here, we’ve compiled a list of 107 deep questions that can serve as a start to some great conversations.

Deep questions to ask your friends

These questions are best suited for calm, quiet environments where you can feel comfortable sharing personal things.

It’s important to not ask these questions too early on in your relationship as they can make someone uncomfortable.

1. What gives you the most comfort?
2. Were your parents good at being parents?
3. Did you ever feel like your parents were your friends?

4. Have you ever felt guilty about not doing something good enough?
5. Are you interested in politics?
6. Do you seek out order or chaos?

7. What’s the point in living, if you’ll end up dead anyway?
8. What do you like the most about people?
9. What do you dislike the most in people?

10. What would be a perfect life for you?
11. If you had a chance to talk to god for 10 minutes but knew you would die immediately after, would you do it?
12. Do you think we’d be better off without social media?

13. How is your relationship with your parents?

14. Do you feel like men and women are equal?

15. If you could change your appearance to that of the most beautiful person in the world, if it meant looking like a completely new person, instead of an improved you – would you do it?

16. How do you feel about big corporations?

17. If you have a choice of two similar products, do you ever consciously choose the one made by a smaller company because it’s made by a smaller company?

18. What do you love the most in life?

19. Do you vote?

20. Do you consciously give preference to what’s trendy and fashionable, or to what’s obscure and rather unknown?

21. How would you change the public education system?

22. What would you change in your life if you knew that there was a god?

23. Do you believe in karma? If so, how do you think it works?

24. Is health more important than fun?

25. What do you think about freedom of speech?

26. Do you remember any character-defining moments from your childhood?

27. Is it more important to believe or to know?

28. Do you think the experiences people have on psychedelic drugs are “real”?

29. Does it matter that there’s a light at the end of the tunnel if you can’t get to it?

30. Why do you think older people have a harder time grasping new ideas?

31. Do you think there is an afterlife of any kind?

32. What do you think about veganism as a moral movement?

33. What does love mean to you?

34. Do you find it easy to make changes in life?

35. Do you think it’s possible to have a great life alone?

36. Have you ever felt like you have no regrets in life?

37. What’s one thing you hope to never forget?

38. What kind of classes do you wish existed when you were going to school?

39. What do you think about the current younger generation?

40. Do you have a hard time giving honest critique to someone you love?

41. Is it more appealing to have a career or to do odd jobs?

42. If your family turned away from you for any reason, would you try to get them back?

43. If dishes could be synthesized perfectly, do you think there’d still be any place for chefs?

44. Is falling in love worth it without the happily-ever-after?

45. Do you think bullies often see themselves as bullies?

46. What was the most recent moment that changed your life in a major way?

47. Would you forget a traumatic experience, if you could?

48. How would you describe the feeling you get when you share your food with someone?

49. Do you feel like your clothes are a part of your personality?

50. Do you ever imagine yourself in very negative, but unlikely scenarios? For example in prison, or severely disabled, or maybe doing things you would never actually do in reality.

51. What was your loneliest moment?

52. Would you say you trust people easily?

53. Did you have a long period in life when you didn’t feel like yourself? How did you come back from that?

54. Should humans merge with AI once it becomes an option?

55. Do you ever think about who or what has influenced you the most in life?

56. How would you deal with betrayal?

57. Has any piece of art ever inspired you to change your life in some way?

58. If you had seen someone being robbed or assaulted, what are the chances that you would intervene? In which cases would you do it?

59. What is the essence of well-being?

60. Are your earliest memories positive?

61. Have you gotten closer to the meaning of life in the last 10 years?

62. Have you ever reconciled with someone you were sure you’d never talk to again?

63. If life was nothing but constant pain, would it still be worth living?

64. When’s a good time to start getting serious about one’s health?

65. Do you ever feel like a child?

66. Have you ever in your life thought, “never again”? What was it about?

67. Do people around you see you as you really are?

68. Do you have any regrets?

69. What’s your biggest regret?

70. What’s the best thing about your life right now?

71. If you could magically change one thing in your life, what would it be?

72. If you’ve always been completely honest with someone, and you had to lie to them to save their life, would you find it hard to do?

Deep questions to ask your best friend

These questions are even deeper than the previous questions. They are best suited for someone you know very well.

It can be helpful to balance asking questions and sharing about yourself, so what your friend doesn’t feel interrogated.

1. Have you ever wanted to die?

2. How would you prefer to die?

3. What do you think is the meaning of life?

4. What was the most difficult “goodbye” in your life?

5. What’s your best memory?

6. What’s your worst memory?

7. When was the last time you cried?

8. What do you struggle with the most?

9. Do you feel like a part of society?

10. What kind of role does religion play in your life?

11. What do you think about using population control to prevent overcrowding our planet?

12. If a genie could tell you a truth you’d like to know about yourself, what would you want to know?

13. Who’s your favorite family member?

14. What’s something you’d like to tell your parents that you would never dare to?

15. What’s something you’d do if you know you’d get away with it and no one would never know that it was you?

16. Is there something you’ve wanted to do for a long time but haven’t yet? What would that be?

17. What do you think about abiding the law vs. following your own moral code?

18. How would you feel if your spouse was in love with another person?

19. What do you value most – comfort or personal growth?

20. If you had to choose, would you rather harm yourself, or others around you?

21. Could you commit suicide if you knew it would save the lives of 100 other people? 200 people? 5000? 100000?

22. How do you think porn affects our society?

23. If you only had those two options, would you rather make all drugs illegal, or make all of them made legal?

24. What stops you from lying and stealing? Would you do it if you knew for sure you’d never get caught?

25. Have you ever done what you thought was the “right thing” with catastrophic results?

26. If you knew that you were to die soon, what would you do?

27. Is there ANYTHING that’s too serious to joke about? What would that be?

28. What’s something you think that you think no one else thinks?

29. What’s the angriest you’ve ever been? What happened?

30. Could you bring yourself to kill someone in self-defense?

31. Could you bring yourself to kill someone to save a friend’s life? What if the person you had to kill was innocent?

32. If you could ask the reaper to spare your loved one, what would you tell him?

33. In which situations do you think war is called for?

34. If you ended up in a coma for 10 years, still conscious but unable to communicate, would you want them to pull the plug?

35. If you had to pick one person, who in your family would you miss the most if they died?

Do you have more ideas for deep questions to ask your friends? Let me know in the comments below!

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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