Deep Questions to Ask an AI

Reflective prompts for insight, philosophy, and perspective.

Prompt list

• What’s a belief I might be holding that no longer serves me?
• What does it mean to live a good life in a modern world?
• How can I tell the difference between fear and intuition?
• What are the hidden costs of chasing productivity?
• What does ‘enough’ look like, and how do people learn it?
• If identity is a story, how do we rewrite it without losing ourselves?
• What is the most important question I’m not asking?
• How do we balance empathy with boundaries?
• What does it mean to forgive without forgetting?
• How do people find meaning when life feels random?
• What might future historians find most strange about us?
• What is the role of boredom in a fulfilling life?
• How can someone build courage without becoming reckless?
• When is certainty helpful, and when is it harmful?
• What do we owe to people we’ll never meet (future generations)?
• How do you make peace with things you can’t control?
• What is the difference between loneliness and solitude?
• If you had to define wisdom in one sentence, what would it be?
• What’s a practical way to become more honest with yourself?
• What’s the healthiest way to handle regret?
• What is the strongest argument for humility?
• How do you choose values when you’re overwhelmed by options?
• What does it mean to be ‘authentic’ without being rigid?
• How can we pursue excellence without self‑punishment?
• What does a meaningful relationship require beyond love?

Try this follow-up

• “Give me 3 different answers, each with a different tone.”
• “Ask me 3 clarifying questions, then answer again.”
• “Give an example, then explain why it works.”

Want to contribute? Suggest a prompt.