CROSSTALK · FREE CONVERSATION QUESTIONS
For the conversations we keep putting off. Nobody owes an answer; the person asking can go first.
Start with Warm Up and see where the conversation takes you. Ask one question, listen to the answer, and ask it back. Anyone can pass at any time. There is no rush to go deeper.
Warm Up
- What is a topic your family always avoided when you were growing up?
- What is something you are curious about but feel awkward asking people?
- What is a question you hate being asked, and why?
- What is something you secretly worry about that seems silly out loud?
- What did you learn about money growing up, just from watching?
- What is something everyone seems to love that you just do not get?
- What is a question you wish people asked you more?
- What was a rule in your house growing up that you thought was strange?
- What is something you pretend to understand but do not?
- What topic makes you instantly uncomfortable, and why?
Get Real
- What is something about your childhood that shaped you more than people realize?
- What do you believe happens after we die, or what do you hope happens?
- What is a part of your body or appearance you have made peace with, or are still working on?
- What is something you have never told your parents?
- What is a mistake that changed the direction of your life?
- What is your relationship with faith or spirituality right now?
- What is something about money that stresses you out?
- What is a family silence you have noticed but nobody names?
- What did you believe when you were younger that you have completely let go of?
- What do you wish you had been taught about your body growing up?
Go Deep
- What is something you are ashamed of that you think you should let go of?
- When was the last time you cried, and what was it about?
- What is the loneliest you have ever felt?
- What do you want people to say about you when you are gone?
- What is something you have never said out loud to anyone, and are you willing to say it now?
- What is a regret you think about more than you admit?
- What do you think about your own death, if you let yourself?
- What is something you wish you could ask a parent, living or gone?
- What part of you do you hide from the people closest to you?
- What would change if you stopped keeping it to yourself?
Found a question you want to ask someone? Send them this page.