Real Conversation Questions

Here are three sets of questions to spark real conversation with people. Each set will be more personal and require more depth than the last.

How do you start? Get together a group of friends or strangers and split into small groups (three to five people). You select someone else in your group to choose a random number (i.e., a number between 1 and 20 if there are twenty questions), then read them the corresponding question. They’ll answer it, and after they answer it, it’s their turn to select someone to answer the next question. I recommend that you spend thirty minutes on the first set, forty-five minutes on the second, and at least an hour on the third.

Make sure you establish a judgment-free zone. Be kind to each other. Some of these questions will get you out of your comfort zone, and while that’s part of the point, you should always be able to ask for a new question if you’d rather not answer the one you’re given. If someone asks you for a new question, respect their wish; don’t coerce them to answer the initial question, even as a joke. Vulnerability isn’t possible without trust.

Let's Get To Know Each Other

1. What was the best part of your day? Week? Year?
2. Tell me something about yourself that you wouldn’t mention the first time you met someone.
3. What’s the best gift you’ve ever given or received?
4. What’s your aesthetic? How did you arrive at it?
5. Do you have any nicknames? If so, what’s the story behind them?
6. When was the last time you did something for the first time?
7. What is your latest discovery about or in the city in which you live?
8. Would you like to be famous? In what way or for what?
9. What’s your best memory from high school?
10. What’s the best compliment you’ve ever received?
11. What would constitute a perfect day for you?
12. If you could gain any quality or ability, what would it be?
13. Give the choice of anyone in the world, who would you want as a dinner guest?
14. What’s a work (book, movie, etc.) that shaped the person you are today?
15. Tell me about a time that you were spontaneous.
16. What’s the most illegal act you’ve ever done and are comfortable sharing?
17. When did you last leave your comfort zone?
18. What was your last epiphany?
19. Would you pick a different career path if you did life again?
20. What’s one specific fact about what it’s like to live in your particular body?

Let's Get Deep

1. What was your most memorable first kiss?
2. With whom do you have the best connection in your family? Why?
3. What’s the most memorable date you’ve ever had?
4. Tell me about your biggest crush.
5. Who do you respect most in your life? Why?
6. Do you have an enemy? If so, why?
7. How did your best friend become your best friend?
8. How did your parents’ values shape your career choice?
9. What do you value most in a friendship?
10. For what in the past year do you feel most grateful?
11. Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?
12. What’s your greatest accomplishment?
13. What’s an embarrassing moment in your life that you still remember?
14. What does it mean to you to live a good life?
15. What experience have you had that made you a more compassionate person?
16. When was the last time you faced a big ethical dilemma? What did you do?
17. What brings you joy?
18. Do you feel fulfilled by your work? Why or why not?
19. When was the last time you were really proud of yourself?
20. What’s the most important self-discovery you made about yourself in the past year?
21. What’s an experience in your past that really shaped your worldview? Why?
22. How do you hope you’ll change as a person in the future?
23. What excites you most about the world in which we live?
24. What frustrates you most about the world in which we live?
25. What are three of your personal qualities of which you’re most proud?

Let's Get Deeper

1. What have you always wanted in romantic relationships but never had?
2. If you were to die with no warning, what would you most regret not telling someone? Why haven’t you told them yet?
3. What liberates you?
4. Do you have enough love and affection in your life? Why or why not?
5. Tell me about your hardest breakup and why it happened.
6. What were the major tipping points in your life that shaped your identity most? How did they affect you?
7. What’s your biggest insecurity?
8. Tell me about a time that someone really hurt you.
9. Tell me about a time that you really hurt someone else.
10. What makes you look down on other people?
11. What do you think makes other people look down on you?
12. Imagine you’re a parent. How would you raise your child differently from the way you were raised?
13. How do you feel about your relationship with your mother?
14. How do you feel about your relationship with your father?
15. Are your passions, morals, ideals, etc., consistent with the way you live your life? If not, why not?
16. How do you assign self-worth?
17. If you knew that, in one year, you would die suddenly, would you change anything about the way you’re living now? Why?
18. What life experience made you grow the most?
19. What’s your most treasured memory?
20. Are you content? Why or why not?
21. If you could change one decision you made in your life, what would it be? Why?
22. When did you last cry in front of another person? By yourself?
23. What’s the most depressed you’ve ever been? What happened?
24. What’s the hardest experience you’ve ever had to undergo?
25. What made you feel most insecure in your childhood?
26. What’s your biggest regret?
27. What’s a major problem you’re facing in your life right now?
28. What do you see as your responsibilities to the world? Your loved ones? Yourself?
29. What are three of your personal qualities of which you’re most ashamed?
30. Where in your life are you giving more than you’re taking? What about taking more than you’re giving?