Deep Questions Wheel

40 questions that skip the small talk

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Entries

What’s a belief you held for years and then let go of?
What would you do if no one could judge you?
When did you last change your mind about something important?
What does a perfect ordinary day look like for you?
What’s something you’ve never told your parents?
Who knows you better than anyone, and how?
What memory do you go back to when life gets hard?
What do you want to be remembered for?
If you had one year left, what would you change?
What’s the kindest thing a stranger has done for you?
What’s a dream you gave up on, and why?
What do you need more of in your life right now?
What do you need less of in your life right now?
Which version of yourself are you most proud of?
What’s a compliment you’ve never forgotten?
What scares you about getting older?
What’s the hardest goodbye you’ve ever said?
What lesson did you have to learn twice?
What does love mean to you?
What part of your childhood still shapes you today?
When do you feel most like yourself?
What question are you afraid to ask yourself?
What would your younger self think of you now?
What do you pretend to care about but don’t?
What’s the best decision you almost didn’t make?
What are you still trying to prove, and to whom?
What do you think happens after we die?
What habit are you quietly proud of breaking?
Who do you owe an apology to?
What makes a life well lived?
What’s a risk you’re glad you took?
What would you tell your 16-year-old self?
What do people get wrong about you at first?
What do you find hardest to forgive?
What are you grateful for but rarely mention?
If you could relive one day, which would it be?
What truth did you avoid for too long?
What does home feel like to you?
What do you hope never changes about you?
What would you do if you knew you couldn’t fail?