What’s your favorite cuisine? What’s your mission in life? Good conversation sometimes needs prompting, and this list of questions will do just that.
“Conversation is the most human and humanizing thing that we do,”
says MIT professor Sherry Turkle, who has spent much of her career studying human connection and its relationship to technology. “It’s where empathy is born, where intimacy is born—because of eye contact, because we can hear the tones of another person’s voice, sense their body movements, sense their presence. It’s where we learn about other people.”
Few experiences are more rewarding than exploring important questions alongside our loved ones. Conversation draws us closer to one another and the world through the shared use of reason and emotion. But, like any art, it takes practice and patience. Sometimes it can be difficult to know how to start a conversation, and at other times it can be helpful to have a blueprint for deepening a relationship. To that end, we’re happy to present a list of 50 more conversation-starting questions (and if you missed them, here were the
first 50).
Getting to Know One Another Better
1. Who was your closest friend growing up? What brought you together?
2. Who is your closest friend now? Why?
3. Who was your childhood hero? Is that person still your hero? Why or why not?
4. As a child, what did you want to be when you grew up?
5. Describe a formative experience you had during high school.
6. Do you think our character is set in childhood, or does it continue to change over the course of our lives?
7. What piece of music best describes or expresses you and why?
8. If you could only reread one book for the rest of your life, what would it be and why?
9. Describe your ideal day.
10. What’s a fear you have that not many people know about?
11. If you’re having a stressful day, what activities never fail to calm and relax you?
12. What’s something you have that you don’t think you deserve?
13. What’s your most prized possession?
14. What’s something you do that you think is probably a waste of time?
15. If you have traveled internationally, what was your favorite country to visit? Why? If you haven’t, what country would you like to visit? Why?
16. Describe a time when you felt like giving up on something. Did you persevere, and if so, how?
17. If you were to switch careers, what would you switch to?
18. What’s your favorite cuisine?
19. Where do you go when you need some peace and quiet?
20. What’s something you didn’t want to do but turned out to be a rewarding experience?
21. What do you hope to be remembered for after you die?
Great Quotations
22. G.K. Chesterton once wrote, “Do not be so open-minded that your brains fall out.” What do you think he meant by this?
23. “The secret of getting ahead is getting started.” (Mark Twain). Do you agree or disagree? Do you have examples from your own life?
24. Socrates famously said, “The more I know, the more I realize I know nothing.” Is that true in your experience?
25. “Success is walking from failure to failure with no loss of enthusiasm.” (Winston Churchill). Do you agree or disagree?
26. “People who get too far from fundamental things, from ploughing and reaping and rearing children, lose something that is never restored by any progress or civilization.” (G. K. Chesterton). Do you agree with Chesterton’s assessment? What does he mean by “fundamental things”?
27. “If I can stop one heart from breaking, I shall not live in vain,” wrote the poet Emily Dickinson. Do you think this is a worthy life goal?
28. In the beloved children’s novel “The Little Prince,” Antoine de Saint Exupéry wrote, “It is only with the heart that one can see rightly; what is essential is invisible to the eye.” What does he mean by this?
29. “All that is gold does not glitter.” (J.R.R. Tolkien). Describe an occasion when you encountered something or someone that did not glitter, but was still truly gold.
30. “Consider your origin. You were not formed to live like brutes but to follow virtue and knowledge.” (Dante). How do we avoid “living like brutes”?
31. “The heart of another is a dark forest, always, no matter how close it has been to one’s own.” (Willa Cather). Is this true?
32. Who’s your favorite author and why?
America the Beautiful
33. What’s the best U.S. state?
34. What’s something that unites all Americans?
35. What important subject are most Americans ignorant about (if any)?
36. What makes you most proud of the United States?
37. Who was the greatest American president and why?
38. What’s the best and worst thing about the United States?
The Big Questions
39. What is the purpose of art?
40. What is a family? What is the purpose of a family?
41. If you’ve lost someone, what do you wish you could have told them before they passed?
42. What is the definition of love?
43. How do we make the world a better place?
44. If a recent high school graduate asked you for life advice, what would you tell them?
45. What’s your mission in life?
Just for Fun
46. Do you believe in cryptids (Bigfoot, Loch Ness Monster, etc.)?
47. What’s something unusual that you collect or would like to collect?
48. If you were an animal, what animal would you be?
49. Which decade had the best fashion? The best music?
50. If you had the opportunity to meet any historical figure, who would you choose?
