100 Questions
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What have you come to appreciate about me that you didn't when we first became friends?
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What do your friends love you in spite of?
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what have you worked the hardest to change about yourself?
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are you working hard to change anything about yourself now?
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what have you come to understand about yourself over the last couple years?
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what do you appreciate about yourself that other people don't always notice?
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what's something you never thought you could do, but did?
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When’s the last time you surprised yourself?
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Has anything inspired you recently?
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what's something you wanted to change about yourself but later came to accept?
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What do you want me to think of you?
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Is there a version of yourself you're afraid to become?
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What trait do you most admire in others that you wouldn't really want to have in yourself?
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Which of your friends are you most proud of?
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Which compliments make you feel best?
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Which compliments (that you get regularly) do you not like that much?
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What's something about yourself you've had trouble accepting (but still want to)?
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What do you think your closest friends would most like to change about you?
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Let's say you're 120 and looking back at your life. what would it need to have included for you to feel completely satisfied with it?
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What is the most exciting part of the trajectory you're currently on?
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What's the difference between who you are and the kind of person a younger you wished you would be?
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When do you feel like you belong? / What was the last time you felt a particular sense of belonging?
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Can you describe a day you’d be willing to have over and over for the rest of your life?
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If we asked the person who loved you most what it is they love about you, what do you think they'd say?
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What are some of your most important identities, and what are some misconceptions you think people that aren’t from that background have about it?
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Which parts of yourself do you feel like you understand least?
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Describe a moment when you felt particularly yourself
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What’s something you’ve done that absolutely terrified you?
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Whose validation makes you feel best?
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Whose validation do you wish you wanted less?
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What’s the last especially emotional movie TV or book experience you can remember?
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What are some of the defining traits of your family? Your friend group?
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Which member of your family do you have the most contentious relationship with and why?
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What do you nerd out about and how did that interest develop?
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When do you feel most in touch with your inner-child?
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Have you experienced any exceptional acts of kindness from a stranger before?
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What is your favorite memory of me?
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What do you think I like most about you?
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How has your life been different than what you’d imagined?
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How would you like to be remembered?
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If this was to be our very last conversation, is there anything you’d want to say to me, or me to you?
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What qualities do you judge most in other people?
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What qualities do you judge most about yourself?
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What are you interested in that most people aren’t?
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Are there any aspects of yourself you know should change, but haven’t started working on?
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What’s the hardest you’ve ever worked?
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If you had to take an entirely new path from the one you’ve chosen, what path would it be and why?
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What do you think your most and least noticeable insecurities are?
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What is an insecurity of mine you’ve noticed?
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What is something you only recently formed an opinion about?
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What mistakes do you make over and over again?
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What have you created that you’re most proud of?
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What’s the best thing you got from your parents?
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What are your comedy influences?
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What movies, TV, or books do you cherish/consider a part of who you are?
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What do you give good recommendations about?
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Is there anything you one day hope to be an expert in?
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Is there anything you value now that you hope you won’t value in the future?
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Is there anything you don’t value now that you hope you’ll value in the future?
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In what areas of your life (if any) do you feel a sense of ambition? What does that mean to you?
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What was the last rant you went on?
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Which of your traits are you most hoping to pass down to your children (or pets, if no children. [Or local goonies-style friend group you're a surrogate parent for, if no pets])
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Do you feel a special connection to any historical periods?
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Are there any periods of history you'd like to learn more about? Why?
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Do you feel like your life has had phases? What are they?
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Have you ever had to admit something to yourself that you didn't want to admit?
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What have you grown out of in the last few years?
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Is there anything in your life you think you’ll grow out of?
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What media helps when you’re upset?
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Have you ever been afraid you'll grow up to be like one or both of your parents? How so?
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Has there ever been a time where you ended up feeling unexpectedly close to someone?
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Who was the last person you confided in and how did it go?
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Who and what has been bringing you joy lately?
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Who are you trying to be more like? Less like?
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How often do you feel lonely?
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What habit are you proudest of developing?
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Are you looking forward to accomplishing anything?
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What fills you with energy?
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What characteristics of yours make you feel most confident?
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What was your last obsession?
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Where in your life did you used to not feel like you were “enough,” but now do?
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What are areas you’re learning to feel like “enough” in?
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What does really excellent emotional support look like for you?
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What romantic gestures from your past have meant the most to you?
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What does it mean to you to be cared for?
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Do you feel spiritual or religious, and if so does your spirituality or religiosity change the way you live?
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In which areas of your life are you gaining confidence?
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What in your life saps your energy and how do you recharge?
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In what ways are you a positive influence to those around you? Negative?
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What’s the last argument you won?
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Do your friends gas you up? How?
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Do you feel like your life path has become any clearer over the last few years?
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What’s something you find interesting about someone in the room?
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Who was the last person to inspire you that you don’t know? That you do know?
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What is the biggest change in yourself you attribute to your partner/closest friend?
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Which culture other than your own do you know the most about?
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Which culture other than your own do you feel most connected to?
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What’s your favorite evil company?
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What’s the hardest thing you do for fun?
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What are you learning to appreciate about yourself that you hadn’t before?