For the past 3 years, Whenever I’ve had an interesting question, I’ve written it down here. These are some of my favorite questions to ask. Hope you find hem interesting!
CHILDHOOD
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When you were little, what were you praised on?
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When you were little, what didn’t make sense to you?
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When you were little, what did you like to do?
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What’s something you tried to convince yourself to like? Why?
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What dark things did you really struggle with when you were younger? What about now?
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What phases did you go through?
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When was a time someone took advantage of you?
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When was your lowest couple weeks in your life?
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Who was the first person you were attracted to?
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How did your parents hurt you?
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At what time were you happiest in life?
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What smells bring you back to childhood?
FEELINGS
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What do you care most about right now?
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What gets you excited?
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Do you have any party tricks or hidden talents?
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If you only had 3 wishes, what would you wish for?
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What makes you feel the best inside? Why?
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What obsessions do you have? What are you interested in now / were?
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What would be the funnest thing to do with your friends?
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When is it easiest to love yourself? Why?
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What country do you find the most exotic? What about it in particular?
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What do you daydream about? What does that signify you want in your life?
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What would be the quickest way to get to know you?
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What is the best song of all-time? Why?
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When you’re sad, what do you do? Who do you talk to? When is it usually?
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What makes you feel the worst inside? Why is that?
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What are you presently anxious about? Upset? Excited?
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What makes you angry? Why does that make you upset?
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When was the most stressful period of your life?
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When is it hardest to love yourself? Why is that?
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When in your life were you the saddest? The most anxious?
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When was the last time you cried? What was it over?
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What are you scared of in the future? Why does that scare you?
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What is something from the past that you miss and wish would come back?
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If you were on your deathbed, who would come to visit you? Who would bring you flowers?
WANTS
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In 5 years, what would your ideal self be like? What would they do? What would they have?
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What would your ideal life look like in 5 years?
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What are the top 3 questions you wish you knew the answer to?
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What things do you want? Skills? What do you most want?
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Who would be the most interesting person you could meet in the next 3 months?
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Think of people you envy. What is it that you envy about them?
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What part of yourself are you most dissatisfied with?
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What part of your life are you most dissatisfied with?
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What non-malicious comment about yourself would hurt you the most?
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What compliment would make you happy the most?
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What parts of other people would you want to “steal”?
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Who embodies some of the character traits you value most? Who are you envious of?
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In the future, do you think you will get married? Have kids? Be in a long term relationship with someone? House or apt? Move away from here? What job?
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What do you want to give to people?
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In your ideal life, what would people say about you when you weren't there? How do you think your [best friend] would answer this question?
THOUGHTS
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What’s the one big thing on your to-do list you’ve been avoiding?
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What do you think about often when you're lying in bed?
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What have some of your best thoughts been?
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What is something controversial you would wear on a t shirt if you made it
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If you would wake up somewhere besides [city they live in] where would it be?
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What’s one of the best ideas you’ve heard recently?
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What do you like to think about?
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What do you want?
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When it comes to something you’re interested in, what questions do you ask?
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What subject could you see yourself completing your Phd in?
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What is something a lot of people pursue that you think is useless to?
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What have you changed your mind about in the last few years? Why?
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Thought experiment: What do you believe may be true, even though you can't prove it?
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What’s your dark side? What parts of yourself do you usually hide from others?
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Who do you find yourself talking with in your head?
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If your younger self got on the bus with you on the ride home and they had to sit next to you, what would you say to them before they got dropped off?
HABITS OF ACTION
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What youtube do you watch?
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What are your bad habits?
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What do you struggle with?
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Do you have any rituals that you do as you go about your day?
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Do you have different personalities with different people?
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What are your good habits?
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What “productive” things do without convincing yourself that you should do it?
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What have been the most valuable youtube videos you’ve watched?