60 Deep Questions
Deep questions do not need a special occasion, but they do need a safe setting. They suit your partner, close friends and conversations with yourself. Whoever asks them should be ready to give their own answer too. The list has three sections: about you, about relationships, and about what remains.
Take your time with each question and allow silences. The goal is not to get through the list. In HYTCH, follow-up questions take your conversation five to six levels deeper into the same topic, exactly where you are right now.
The questions
About you
- 1
What do you believe about yourself that is probably not true?
- 2
What are you most afraid of, if you are honest?
- 3
What would you do if you knew for sure you could not fail?
- 4
What is the sentence you heard too often as a child?
- 5
When did you last surprise yourself?
- 6
Which version of yourself do you miss?
- 7
What makes your life worth it right now, in one sentence?
- 8
What pain are you carrying that nobody knows about?
- 9
What would you tell yourself ten years ago?
- 10
What would the you of ten years from now tell you today?
- 11
What do you pretend to want because others expect it?
- 12
When were you last truly honest with yourself?
- 13
Which decision do you regret, and who knows about it?
- 14
What is the fear behind your greatest strength?
- 15
Which role do you play too often, and who are you without it?
- 16
What is the difference between who you are and how you are seen?
- 17
Which wound made you who you are?
- 18
What was the moment you became an adult?
- 19
What would you be willing to lose to stay yourself?
- 20
What do you want to let go of before this year ends?
About relationships
- 21
Who have you not forgiven yet, and what is that costing you?
- 22
Who should you be grateful to that you have never told?
- 23
Who have you lost without them dying?
- 24
What is the hardest thing you have ever said to someone?
- 25
What is the hardest thing anyone has ever said to you?
- 26
What is a truth about your family you did not want to see for a long time?
- 27
When did you last ask for help, and how did it feel?
- 28
What do you understand about your parents today that you did not understand before?
- 29
What does love mean to you, without using the word?
- 30
What would you like to hear that nobody tells you?
- 31
Who have you disappointed, and did you ever make it right?
- 32
Which friendship did you leave when you should have stayed?
- 33
What do you need from people that you cannot give yourself?
- 34
When did you last truly see someone instead of just listening?
- 35
Which expectation of others makes you unhappy?
- 36
Who really knows you, and how do you know that?
- 37
What did a person who is no longer in your life teach you?
- 38
When did you last hurt someone and not admit it?
- 39
What would you say to a person you have not spoken to in years?
- 40
What do you want the people who matter to you to never forget about you?
About what remains
- 41
What does home mean to you, beyond places?
- 42
What do you believe without being able to prove it?
- 43
What was the loneliest moment of your life?
- 44
What has shaped you more: what happened, or what did not happen?
- 45
What have you made peace with?
- 46
What will you never make peace with?
- 47
What do you want people to say about you after you die?
- 48
What holds you when everything else falls away?
- 49
What is a wish you gave up without ever saying it out loud?
- 50
If your life were a book, which chapter would you cut, and which would you read again?
- 51
What would you do if you knew you had one year left?
- 52
What matters more: being understood or being loved?
- 53
Which question have you been asking yourself for years without finding an answer?
- 54
What have you kept from your childhood that you never want to lose?
- 55
What is happiness for you, if you do not confuse it with success?
- 56
When did you last feel that something is bigger than you?
- 57
Which mistake would you make again because it brought you to yourself?
- 58
What would you like to know about life that nobody can tell you?
- 59
What remains of you when you subtract job, possessions and roles?
- 60
What is the one thing you would like to be remembered for?