48 Deep & Fun Questions to Ask Your Brother

If you’re struggling to find topics to talk about with your brother, check out our list of meaningful questions and conversation prompts. We’ve included a range of topics, from deep questions about themselves and life to fun questions on dating and relationships.

If you have an amazing brother, why not get him a Remento book to turn his stories into personalized memory book as a gift?

Here are our favourite questions across different topics: 

• Best Question About Him: Talk about the most exhilarating adventure you have had.
• Best Question on Life: If you could relive your life, what would you do differently?
• Best Question About His Viewpoint: Talk about what you would change in your country if you had the power
• Best Question on Family: Talk about a moment when you felt grown up
• Best Question on Relationship: Talk about a high school sweetheart

Questions About Him

1. What has been your favorite car to date?
2. How did you get the money for your first car?
3. What is your favorite music genre?
4. Do you have a favorite composer or band?
5. What is your all-time favorite movie?
6. What movie made you laugh the most?
7. What food did you hate as a child?
8. Where is the most interesting place you have been?
9. Talk about the most exhilarating adventure you have had.
10. Can you describe a particularly challenging adventure?
11. Do you like to cook or eat at restaurants?
12. Has your taste changed over time?
13. Do you prefer to watch in theaters or at home?

Questions About His Life

14. How would you spend your time if you didn’t have to worry about money?
15. If you could have any job, what would you do for a living?
16. What are you most proud of?
17. Was there a moment in your childhood when you were proud of yourself?
18. Are you proud of any particular educational achievement?
19. Who are you most proud of in your circle?
20. Who has had the most influence on your life?
21. Talk about the kindest thing someone's ever done for you.
22. Talk about the most positive change in society during your lifetime.
23. If you could relive your life, what would you do differently?
24. Talk about whether or not you are a good person.

Questions About His Viewpoints

25. How long do you want to live?
26. What do you think happens after we die?
27. What are your thoughts on evil?
28. How important is it to have a purpose?
29. What are your thoughts on the impact of social media?
30. What discrimination or prejudice have you experienced?
31. Talk about what you would change in your country if you had the power

Questions About Family And His Childhood

32. What were your favorite games growing up?
33. Tell a story about one of your siblings
34. Talk about your favorite family holiday
35. What do you admire most about your mother?
36. What do you admire most about your father?
37. What were you afraid of as a child?
38. Talk about a moment when you felt grown up
39. Talk about a lesson from your childhood that has stuck with you
40. What would your ten-year-old self say to you now?
41. If you could go back and be a child again, how would you change things?
42. Talk about your childhood friends
43. What were you most passionate about as a child?

Questions About Dating & Relationships

44. Describe your very first date
45. Talk about a high school sweetheart
46. Talk about disappointing dates
47. Did you ever get dumped?
48. Do you kiss on a first date?