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If you’d like to get in deeper with someone, or even to get to know yourself better, consider asking one or more of these questions. The later questions are particularly probing.
What are you thinking about these days?
Is there something you're looking forward to?
Tell me your life story in a few minutes.
What's been your happiest and saddest moment?
What’s your most vivid memory?
Do you have a favorite saying?
Who do you most admire?
Has there been a book, article, or movie that has strongly influenced you?
What’s your favorite possession?
What’s the best advice you’ve ever received?
Tell me a story about you.
If you knew then what you know now, what age do you wish you could be? Why?
What’s the top item on your bucket list?
What would you do with an extra million dollars?
What adjective best describes you?
What would surprise me about you?
What do people misunderstand about you?
What’s an unusual, even weird, value you hold?
What do you like best and least about yourself?
What are you most and least proud of?
What would be your perfect day?
What would be your nightmare day?
When did you last laugh?
When did you last cry?
What do you most hope for?
What makes you angriest?
If you didn’t care what anyone thought, what would you do?
What do you give a damn about?
What’s something about yourself you'd want to change?
What’s something about yourself you’d be sad to lose?
How do you feel about your mother? Your father? Your siblings?
What is your happiest and saddest memory of an experience you had with your parent?
What is your happiest and saddest memory of an experience you had with your sibling?
What is your happiest and saddest memory of an experience you had with a past or current romantic partner?
What’s something about you that your best friend would have to accept?
What is your biggest regret?
If you could have one life do-over, what would it be careerwise?
If you could have one life do-over, what would it be relationship-wise?
If you could have one other life do-over, what would it be?
What do you want, what do you really want?
What’s the biggest source of stress or anxiety in your life?
What do you wish you could talk about but don’t?
Is there anything you’ve been scared to tell me that you want to tell me now?
What are you most afraid of?
What’s something you’re afraid is true about you?
Do you ever feel like a fraud? If so, about what?
What would be your memoir's title?
If you were to die now, what would you regret that you didn’t do?
If you were to die now, what would you regret that you didn’t say?
If this were our last conversation, what would you tell me that you wouldn't have said before?
What question would you most want to ask me?
