125 Deep Questions to Ask Friends

By Sandra Aninwaeze Updated on: May 9, 2024 Fact Checked by Mariel Collado

Discover new details about your friends and strengthen your bond by asking them these 125 deep questions. 

Why Should I Ask My Friends Deep Questions?

When you’ve made a new friend, you would want to learn more about them, so you know if you can trust them. One tactic is to ask them questions. You can start with surface-level questions, but it can get boring and not reveal enough to give you peace of mind about someone’s character. As the friendship develops, consider broaching subjects that bring you closer, thanks to getting to know each other on a more personal level. 

Deep questions open the door to honest conversations. Becoming comfortable discussing these matters creates a safe and respectful friendship where you can both be vulnerable without prejudice.

Furthermore, deep questions tell you about someone’s values and character. As you learn more, you’ll know which friends are the ones you can trust in challenging times. 

Also, a deep question could help a friend share about important matters in his or her life. They may have a need to talk about it, but don’t know how to start such a discussion. Your courage to ask some deep questions can be what they need to get something off their chest.  

You might have skipped these questions with your existing friends until now, but it’s never too late to start solid conversations with them. Pick topics from the list that will reveal facts you’ve always wondered about – or facts you feel the need to share yourself.

60 Deep Questions About Life

1. What’s the greatest lesson you’ve learned so far?
2. What do you value most in life?
3. What are you thankful for?
4. Where do you see yourself in the next five years?
5. What are your passions?
6. Who is your role model?
7. Have you ever had a near-death experience?
8. What’s your greatest regret in life?
9. Do you consider yourself happy right now? 
10. When was the last time you cried?
11. What’s your favorite childhood memory?
12. What’s your worst childhood memory?
13. Did you experience any childhood trauma?
14. Would you consider yourself a religious or spiritual person?
15. What’s your biggest accomplishment so far?
16. Do you believe in fate? 
17. Do you feel your age?
18. Where do you go for some alone time? 
19. What did you wish for as a child?
20. How do you want to be remembered?
21. Do you have any secrets that would change your life if revealed?
22. What’s one mistake you made in the past that you would like to correct?
23. If you only have 24 hours to live, how would you spend it?
24. What advice would you give your younger self?
25. If you could change one thing about yourself, what would it be?
26. What’s on your bucket list?
27. What’s your most treasured possession?
28. Do you believe in reincarnation? 
29. If you could wish for three things, what would they be?
30. At what point in your life did you feel you were the luckiest person on earth?
31. Have you ever lost someone close to you?
32. What fictional character do you most relate to?
33. Are you a morning or an evening person?
34. What is your conflict resolution style?
35. What’s your coping mechanism?
36. Do you judge a book by its cover?
37. Do you keep a journal?
38. What/how do you feel at the moment?
39. What and who inspires you?
40. What was the best phase of your life?
41. What was the worst phase of your life?
42. What’s the best advice you can give to someone at the moment? 
43. What’s your best personality trait?
44. What’s your worst personality trait?
45. Do you believe in the afterlife?
46. What’s the best gift you’ve ever received?
47. Are you an introvert or an extrovert?
48. If you’re in a bad mood, do you want to be left alone or talk to someone?
49. What’s one thing that people misunderstand about you?
50. What’s the darkest thought you’ve ever had?
51. What activity makes you feel at ease?
52. Do you have nightmares or recurring dreams?
53. How would you define beauty?
54. Do you think men are more rational and women are more emotional?
55. What are your opinions on gender roles and feminism?
56. Does the idea of getting older scare you?
57. What’s your greatest fear?
58. Who are you most afraid of losing?
59. Would you rather be rich and famous or rich and unknown?
60. How would you describe your mental health right now?

13 Deep Questions About Your Friendship

1. How would you describe our friendship?
2. What’s your favorite thing about me?
3. What’s one thing about me you dislike?
4. If there’s one thing about me you could change, what would it be?
5. Who would you call first if you were in trouble?
6. How do you think your friends would describe you?
7. How would you describe me?
8. What’s the most important thing about our friendship?
9. What do you enjoy doing with me the most?
10. How can we be better friends?
11. When we first met, what did you think of me?
12. If we could do one thing together before we die, what should it be?
13. If we organize a friend-weekend, what should it look like?

11 Deep Questions About Family

1. What’s your relationship with your parents like?
2. Do you feel loved by your parents?
3. What’s your favorite memory with your family?
4. Which parent are you closer to and why?
5. When was the last time you and your family went on vacation?
6. Do you consider your family a safe space? 
7. What would you do if your parents didn’t like your partner?
8. Are there any extended family members you dislike and why?
9. Who’s your favorite extended family member?
10. Do you have a favorite sibling?
11. What’s your favorite family tradition?

17 Deep Questions About Love

1. Do you believe in soulmates?
2. Have you ever been in love?
3. Who was your first love?
4. Who was your first kiss? How was it?
5. Do you believe in love at first sight?
6. Who do you love the most?
7. Do you want to get married someday?
8. Do you want to have children?
9. What’s your idea of a perfect date?
10. Would you move to another country for love?
11. What is the most important relationship in your life right now?
12. What’s the most romantic thing someone has ever done for you? 
13. What’s the most romantic thing you’ve ever done for someone?
14. What qualities do you look for in a potential partner?
15. What do you find attractive in a guy/girl?
16. What’s your ideal type?
17. What do you think is the most attractive thing about you?

11 Deep Questions About Relationships

1. What red flags do you look out for?
2. What do you think is your red flag?
3. How long was your last romantic relationship?
4. What’s your best relationship advice?
5. What do you think about dating sites and apps?
6. Can you forgive a cheating partner?
7. What did you learn from your last relationship?
8. What do you think about sharing your passwords with a significant other?
9. Do you stay in touch with your exes?
10. What went wrong in your last relationship?
11. How long do you think a couple should date before getting married?

5 Deep Questions About Success and Failure

1. How would you define success?
2. Currently, do you regret the path you’ve taken in life?
3. Have you ever felt that you’ve failed in life?
4. If you can choose a different career path, what would it be?
5. What’s one thing you can never fail at?

8 Other Deep Questions to Ask Friends 

1. Do you believe in a parallel universe?
2. Do you think you will survive a zombie apocalypse?
3. Do you believe in aliens?
4. What would you change about the world if you had the power?
5. What superpower would you like to have?
6. If you could choose any century to live in, what would it be?
7. Would you rather time travel to the past or the future?
8. What fictional world would you like to live in?

Experts’ Tips: How to Be a Better Friend

Friendship is a two-way street. If you want good friends, you must be good to them as well. Here are some ways you can be a better friend:

1. Celebrate their achievements and support them when they fail.
2. Check up on them as often as you can.
3. Be honest and open with them.
4. Always offer your support, even when they don’t ask for help.
5. Show them you’re grateful for their friendship.
6. Don’t judge their past or bring up their past in an argument.
7. Don’t hold grudges. Try to sort out your differences in a mature way and learn to communicate better.
8. Be a good listener.
9. Do not share their secrets with other friends.
10. Do not take advantage of their loyalty.

However, if your friend doesn’t reciprocate or appreciate your efforts in strengthening the friendship, we advise you to have a conversation with them. Ask a few of the questions above, and share your concerns during the discussion. If nothing changes, consider cutting them off.

Conclusion 

Engaging your friends in deep conversations helps you understand their viewpoints while creating a deeper connection. You’ll develop empathy for your friends when you know the challenges they’re facing or have faced in the past. You will become more aware of what’s going on in their lives, encouraging you to be a better friend. 

The right questions can even come in handy at the start of a friendship or relationship, to keep a conversation going while texting or when meeting face-to-face. Their answers will help you determine if it’s someone you want to spend more time with.

So, when next you talk to your friend online or in real life, engage them with any of these 125 deep questions to ask friends to help you both talk about what’s really important! Finally, remember to be honest with your friends when they ask you deep questions too!