111 Deep Questions To Ask Your Friend

Whether you’re looking to get to know them better, or simply want to facilitate a more meaningful conversation, asking deep questions will help.

Asking your friend about their hopes, fears, and dreams can help you understand them on a deeper level, and can also help build a stronger bond between the two of you.

So next time you’re looking for something more than small talk, try asking one of these deep questions.

14 Deep questions to ask your friends about yourself

1. What was your first impression of me?
2. What are some things you admire about me?
3. What is your favorite memory of us together?
4. Why do you think we’re such good friends?
5. What are some things you feel like you can’t tell me?
6. What’s something you’ve always wanted to tell me but never have?
7. Is there anything you’re afraid to ask me?
8. What do you think our friendship means to me?
9. What do you think are my three biggest strengths?
10. What do you think are my three biggest weaknesses?
11. What do you think are the three most important things for me to work on in order to improve myself?
12. Do you think I have any blind spots when it comes to self-awareness? If so, what do you think they are?
13. What do you think is the biggest misconception others have of me?
14. Do you think I’m too harsh on myself or too easy on myself? How so?

21 Deep questions to ask friends when bored

1. What do you think is the meaning of life?
2. How do you think people can improve the world?
3. If you could have any superpower, what would it be?
4. What motivates you?
5. How do you define the meaning of happiness?
6. What is your favorite memory?
7. Some deep questions you can ask your friends include:
8. What motivates you?
9. What would you do if you couldn’t fail?
10. What are your biggest fears?
11. What are some things you’re passionate about?
12. How do you define the meaning of happiness?
13. What do you think is the purpose of life?
14. How do you define success?
15. What do you think is the meaning of life?
16. Do you believe that people are truly capable of change?
17. What do people need in order to be fulfilled?
18. How would you describe yourself both physically and emotionally?
19. What is your idea of the perfect relationship?
20. What has been the most meaningful and significant relationship in your life?
21. What are your biggest accomplishments? And, what were the circumstances surrounding them achieving them?

21 Deep Questions to ask friends about Love

When it comes to love, everyone has different experiences and opinions. However, we can all learn from each other by sharing our own stories and asking deep questions.

Here are some thought-provoking questions to ask your friends about love:

1. What are your thoughts on love? Do you believe it’s something that happens naturally or do you think it’s something we have to work at?
2. What are the most important qualities you look for in a partner?
3. Have you ever been in love? If so, what was it like for you?
4. Do you think love is always worth fighting for? Why or why not?
5. Do you think there’s such a thing as “the one”? Or do you believe that there are multiple people out there who could be a good match for us?
6. Do you believe that love conquers all, or that love is just a chemical reaction?
7. How do you know when you’re in love? What are the signs for you?
8. How did you feel when you were falling in love with your current partner? Was it gradual or sudden?
9. What do you think love is really for? Is it just a feeling, or is there more to it than that?
10. Do you think it’s possible to be in love with more than one person at the same time, or do you think that’s cheating?
11. Do you think love is something that people can control, or do you think it’s something that happens beyond our control?
12. What are your thoughts on soulmates? Do you believe in them? What do you think happens to us after we die?
13. Do you think love is always worth pursuing, even if it means making sacrifices? What are your thoughts on compromise in relationships?
14. What does love mean to you?
15. What are the different types of love?
16. Do you think love is necessary for a happy life?
17. How do you know when you’re in love?
18. What are the signs that someone is in love with you?
19. Is there such a thing as true love?
20. What are the biggest challenges in a relationship?

55 Deep Questions to ask friends about life

1. If you could have any superpower, what would it be?
2. What is your favorite book and why?
3. What are some things you’ve always wanted to learn?
4. What’s a place you’ve always wanted to visit but haven’t?
5. What are some foods you don’t like?
6. What is your favorite movie and why?
7. What would you do with a kiosk in your room where you could order anything you want for delivery to your room without even having to speak?
8. What kind of music do you like?
9. Who are some of your role models? Why?
10. What has been your proudest moment?
11. How would you describe yourself both physically and emotionally?
12. What is your idea of the perfect relationship?
13. Do you believe that everyone deserves a second chance? Why or why not?
14. Are there any topics that are taboo for you? Why?
15. Do you have any regrets in life? If so, what are they and why do you regret them?
16. What would you do with a kiosk in your room where you could order anything you want for delivery to your room without even having to speak?
17. If you were given $1,000 right now, what would you spend it on?
18. Do you think people are influenced more by nature or nurture?
19. What do you think is the meaning and purpose of life?
20. Do you believe that everyone has a soulmate? Why or why not?
21. Do you think that love is everything people say it is cracked up to be? Why or why not?
22. What are the deep questions to ask your friend? How can you get to know someone on a deeper level? What are some questions that will help you get to know your friend better?
23. What is your favorite memory from childhood?
24. What are your hopes and fears for the future?
25. How would you describe yourself both physically and emotionally?
26. What are some of the most important lessons you’ve learned in life?
27. Who are the people that have had the biggest influence on your life and why?
28. What are some things you’ve done that you’re proud of, even if they don’t seem like a big deal to others?
29. What do you think is the meaning and purpose of life?
30. Do you think there is such a thing as fate or that everything happens for a reason?
31. What would you do with a kiosk in your room where you could order anything you wanted for delivery to your room without even having to speak?
32. If you could go back and relive one moment from your life again, what would it be?
33. If you had to describe yourself using only three adjectives, what would they be?
34. What’s something you’ve always wanted to do, but haven’t?
35. What are three things on your bucket list?
36. What’s a place you’ve always wanted to visit but haven’t?
37. Do you think people are inherently good or bad?
38. How do you define the meaning of happiness?
39. What has been the most meaningful and significant relationship in your life?
40. What are some of the biggest challenges you’ve faced in your life, and how did you overcome them?
41. What are some of your biggest accomplishments, both professional and personal?
42. What makes you feel most fulfilled in life?
43. What do you do that makes you feel happy and fulfilled?
44. What has been your most meaningful and significant experience?
45. What are your thoughts on religion and spirituality?
46. Do you think that extraterrestrial life exists? Why or why not?
47. Who has had the biggest influence on your life, and why?
48. How would you describe yourself both physically and emotionally?
49. What is your idea of a perfect day?
50. What is your idea of the perfect relationship?
51. What are the most important things that you need in a relationship?
52. What are some things you’ve always wanted to do but haven’t done yet?
53. What about life surprises you the most?
54. Do you have any spiritual or religious beliefs?
55. Are you comfortable with who you are, or are there areas you’d like to change about yourself?

A word from Charismatic Persona

Having regular deep conversations can be a great way to keep your friendship or relationship strong. You may find that you learn new things about each other, and this can help you to grow closer together. If you’re not used to having deep conversations, it can be helpful to ask some questions ahead of time so that you have something to guide the conversation.