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These questions have been collected by me (Josh) over the last few years. I don't take credit for creating the questions (I mean, who could?) but do hope that having them in one place is helpful for your own explorations.

If you'd like, share your responses or stories at www.questionsthatconnect.us
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What do you think I want from life?
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Do you believe there is the 'one' for you?
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Which of your insecurities drives you crazy?
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How would you describe me to others?
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What is one experience you wish to have in the future?
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What do you think is a fundamental moral value we share in common?
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Where do you see yourself in 10 years?
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How many people do you think I've slept with?
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What do you think I'm insecure about?
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What is your biggest fear?
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Are you sexually satisfied?
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If you had to call me by another name, what would it be?
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What's the wisest thing you could teach me?
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What do you think you've missed out on while being in a relationship?
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What's the one thing I could do that would dramatically improve my life?
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Given the choice of anyone in the world, whom would you want as a dinner guest?
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Would you like to be famous? In what way?
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Before making a telephone call, do you ever rehearse what you are going to say? Why?
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What would constitute a “perfect” day for you?
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When did you last sing to yourself? To someone else?
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If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
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Do you have a secret hunch about how you will die?
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Name three things you and your partner appear to have in common.
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For what in your life do you feel most grateful?
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If you could change anything about the way you were raised, what would it be?
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Take four minutes and tell your partner your life story in as much detail as possible.
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If you could wake up tomorrow having gained any one quality or ability, what would it be?
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If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
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Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
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What is the greatest accomplishment of your life?
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What do you value most in a friendship?
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What is your most treasured memory?
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What is your most terrible memory?
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If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
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What does friendship mean to you?
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What roles do love and affection play in your life?
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How close and warm is your family? Do you feel your childhood was happier than most other people’s?
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How do you feel about your relationship with your mother?
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How would you complete this sentence? “I wish I had someone with whom I could share ... “
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When did you last cry in front of another person? By yourself?
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What, if anything, is too serious to be joked about?
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If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
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Of all the people in your family, whose death would you find most disturbing? Why?
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What do you value in life?
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What makes you angry?
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What makes you happy?
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How do you want others to see you?
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If you woke up tomorrow with no fear, what would you do first?
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If you can choose anyone in the world, who would you want as a roommate?
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What is something you never want to do again?
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When did you realize you weren't average?
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If you could freeze time for one hour, what would you do?
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What is one thing that makes you angriest, the fastest?
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What is your idea of perfect happiness?
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What is the trait you most deplore in yourself?
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What is your greatest extravagance?
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On what occasion do you lie?
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What do you dislike most about your appearance?
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Which words or phrases do you most overuse?
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What or Who is the greatest love of your life?
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When and Where were you the happiest?
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Which talent would you most like to have?
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What do you consider your greatest achievement?
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What is your most treasured possession?
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What do you regard as the lowest depth of misery?
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What is your most marked characteristic?
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What do you most value in your friends?
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Who are your heroes in real life?
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What is your greatest regret?
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How would you like to die?
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What are you most afraid to desire?
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Why do you do what you do?
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What helps you trust others?
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What gives you faith in humanity?
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What do you do that is not socially acceptable?
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What is one experience you've had that you don't believe anyone else has ever experienced before?
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What is a belief you would be willing to die for?
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What do you need help with that you are afraid to ask for?
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What would be one of the most difficult decisions you've ever made?
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If today were the last day of your life, would you do what you are about to do today? If not, what would you do instead?
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What is something you would happily fail at?
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When do you feel you can be fully present for the people around you?
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What worries you most about your future?
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What belief are you holding onto that you need to let go of?
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What is your self-talk like?
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What is the biggest mistake you have made?
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What is something on your bucket list you are planning to achieve this year?
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What three identities do you resonate most with?
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What do you like to teach others about?
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What is something that you pretend to understand when you really don't?
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What's the number one change you need to make in your life in the next three months?
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When did you not speak up when you should have?
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In what way are you your own best friend?
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What would you like to gift to someone in your lifetime?
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What do you wish you didn't know?
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What was worth giving up and what do you want back?
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What mistake do you make over and over again?
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In what ways do you take care of yourself?
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What has your inner voice been telling you lately?