Deep Questions

You'll get to know someone better by asking deep questions, which will require more thinking and longer responses. Below are some examples of deep conversation questions that you can ask.

  • What scares you most about the future?
  • Who do you aspire to become more like?
  • What is your biggest goal in life?
  • What do you want your legacy to be?
  • What's one thing that you would like to change about yourself?

  • What do you want to learn more about?
  • What would you like to get better at?
  • What does an ideal life look like for you?
  • Are you a giver, taker or, matcher?
  • What is the best thing about being you?

  • How have you changed from 10 years ago?
  • What advice would you give to your younger self?
  • What was the best thing to you happen in the past year?
  • What was your biggest failure? What did you learn from it?
  • What was the worst thing to you happen in the past year?
  • What's the best advice you've received?
  • What do you miss most about being a kid?
  • What was the most challenging time of your life?
  • What was the biggest sacrifcie that you made? Was it worth it?

  • What is your greatest fear?
  • What is your biggest regret?
  • When was the last time you cried? Why?
  • What do you worry about the most?
  • How and when would you like to die?
  • What was your saddest moment?

  • Do you think you'd be happier with more money?
  • What makes you the most happy?
  • What would a perfect day for you look like?
  • When were you the happiest?
  • Is happiness the most important goal in life?

  • What issues are you most passionate about?
  • How do you measure success? Do you think you're successful?
  • Who influenced you the most?
  • What do you most value in a partner?
  • What is your relationship with your parents like?
  • What's the most important quality to have in a friend?
  • What are you most proud of?
  • What do you like most about yourself?
  • What is most important to you?
  • What matters the most to you?
  • What motivates you in your life?

  • Is it possible to have good without bad?
  • Do you believe in God? Why?
  • What do you think the purpose of life is?
  • What is the meaning of life?
  • Are all people's lives equally valuable?
  • Is freedom or security more important?
  • Is it ever ok to lie?
  • How do you determine if something is right or wrong?

Also see: 101 Conversation Starters | Would You Rather Questions | Random Conversation Generator

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