Pull up a random number generator and ask away!
Remember to create a safe, non-judgmental space for everyone participating. If you’d like to add to the list, feel free to contact me with suggestions for questions.
- What does a perfect day look like to you?
- What’s the best compliment you’ve ever received?
- What is something “weird” you do that you wonder if other people do as well?
- What are you glad you learned as a child?
- What activity makes you lose track of time?
- What will never cease to make you smile?
- How has your day / week / year been going so far?
- When did you last leave your comfort zone?
- What’s the best gift you’ve ever given or received?
- What are the worst and best things about where you currently live?
- How did your best friend become your best friend?
- What do you value most in a friendship?
- How do you hope you’ll change as a person in the future?
- In what ways do you differ most from your parents?
- What are three personal qualities you love most about yourself?
- What are you currently worrying about, if anything? What could happen to make you stop worrying about it?
- What energizes you? What drains you?
- What’s the most illegal act you’ve ever done and are comfortable sharing?
- What character trait instantly makes you respect someone?
- What’s the biggest fight you’ve gotten into, and what was it about?
- Is there someone you knew once but have lost touch with? What happened? Do you know where they are now, and how they’re doing?
- With whom do you have the deepest connection in your family? Why?
- When was the last time you were really proud of yourself?
- What’s an experience in your past that really shaped your worldview? Why?
- What excites you most about the world in which we live?
- What frustrates you most about the world in which we live?
- What is something you never thought you’d be able to do, until you actually did it?
- What, if anything, is too serious to be joked about?
- When do you feel like the best version of yourself?
- What’s something you went through that you wouldn’t wish on your worst enemy?
- What do you want written on your tombstone?
- What does success mean to you?
- How has your relationship with yourself changed over time?
- What is the most pain you’ve experienced in your life?
- Are you currently pursuing what makes you happy? Why or why not?
- Was there ever a moment when you thought you were going to die?
- What wouldn’t you do for someone you love?
- If you died today, what would be your biggest regret?
- Have you ever hit “rock bottom”? What did it look and feel like to you? What situations or decisions led to it? How did you get out, or have you gotten out yet?
- What’s the most important self-discovery you made about yourself in the past year?
- How do you think humanity will go extinct?