Deep 21 Questions

What do you think happens after we die?

If you could know the absolute truth to one question, what would it be?

What do you think is the meaning of life?

Do you believe people can truly change?

What scares you most about the future?

If you could live forever, would you want to?

What would you want people to say about you at your funeral?

Do you believe in fate or free will?

What is the hardest truth you have had to accept?

If you could understand one thing completely, what would it be?

What is one truth about yourself you are still negotiating with?

If you could see a statistic about your life, what would you want to know?

What is one thing you do purely because you are afraid of what happens if you stop?

What is the difference between living and existing, and which are you doing?

What is one belief you hold that you cannot fully explain?

If your life had a thesis statement, what would it be?

What is one thing you sacrificed that you still think about?

What is the most important thing you unlearned?

What is one thing you know now that would have saved you years if you had known it sooner?

What is one thing you are willing to be misunderstood about?

What is the loneliest you have ever felt, and what did it teach you?

What is one thing you think everyone should experience at least once?

What is one thing you think no one should ever have to experience?

If you could apologize to one version of yourself, which one would it be?

What is one thing you are running toward, and one thing you are running from?

What is the most courageous thing you have ever done quietly?

What is one thing you think is worth suffering for?

What is one thing you think suffering does to a person?

If you could know the exact day you die, would you want to?

What is one thing you want to have finished before your last day?

What is one thing you think outlives a person?

What is the most beautiful thing you have ever witnessed that no one else saw?

What is one thing you think beauty is for?

What is one thing you think pain is for?

If you could trade one year of your life for one perfect day, would you?

What is one thing you think money reveals about a person?

What is one thing you think power reveals about a person?

What is one thing you think silence reveals about a person?

What is the most honest conversation you have ever had?

What is one conversation you keep having with yourself?

What is one thing you pretend to be certain about?

What is one thing you are certain about that no one else seems to be?

If you could erase one memory, would you — even if it shaped you?

What is one memory you think made you who you are more than any other?

What is one thing you think you owe the world?

What is one thing you think the world owes you?

What is the most unfair thing you have ever benefited from?

What is the most unfair thing you have ever done?

What is one thing you think forgiveness is actually for?

What is one thing you have not forgiven yourself for yet?

If you could restart life with all your current knowledge, would you?

What is one thing you would do completely differently if no one could judge you?

What is one thing you do only because people are watching?

What is the most free you have ever felt?

What is one thing you think freedom actually costs?

What is one thing you think love requires that people rarely give?

What is one thing you think people confuse with love?

What is one thing you think hope is — a feeling, a choice, or a habit?

What is one thing you hope is true even though you cannot prove it?

What is one thing you fear is true even though you cannot prove it?

If your life was a book, what chapter are you in, and what is it called?

What is one thing you think your younger self would not understand about you now?

What is one thing you think your older self will not understand about you now?

What is the most important question you have never asked anyone?

What is one question you are afraid to ask yourself?

What is one thing you think happiness actually is?

What is one thing you gave up to be happy?

What is one thing you would give up happiness for?

What is one thing you think regret is trying to tell us?

What is your biggest regret so far, and what did it cost you?

If you could witness one event in history, what would you choose?

If you could change one event in your history, what would you choose?

What is one thing you think time does to a person?

What is one thing you think time cannot do?

What is the most patient you have ever been, and what was it for?

What is one thing you are waiting for that you are afraid will never come?

What is one thing you are afraid you already missed?

What is one thing you think makes a life meaningful?

What is one thing you think makes a life wasted?

If you had to defend your life choices to a jury, what would your opening statement be?

What is one thing you think you were lucky to survive?

What is one thing you think someone else was not lucky to survive?

What is one thing you think the universe is — friendly, indifferent, or hostile?

What is one thing you think happens in the moment before a big decision?

What is the hardest decision you have ever made, and how did you make it?

What is one decision you made in a second that changed everything?

What is one thing you think you will believe in ten years that you do not now?

What is one thing you think you will stop believing in ten years?

What is one thing you think is sacred?

What is one thing you think should be sacred but is not treated that way?

What is one thing you would want a stranger to know about the human experience?

What is one thing you think animals know that we do not?

What is one thing you think children know that adults forget?

What is one thing you want to know before you die?

If this was the last conversation you ever had, what would you want it to be about?

What is one thing you think you will finally understand when it is too late to use it?

What is one thing you want to be true about what comes after?

What is one thing you are at peace with?

What is one thing you are not at peace with yet?

What is one thing you think you were put here to do?

What is one thing you think you have been avoiding your whole life?

What is the most important thing you know?

What is the most important thing you do not know?

What is one thing you want someone to ask you before you die?

If you had one final sentence to leave behind, what would it be?