Questions to Ask for Deeper Conversations

When I am having a conversation with someone, I like to make it interesting by asking unique questions so that I get to know this individual at a new level. I think that these questions get us to reflect on new scenarios or learn more about ourselves. 

I thought it would be good to compile a list of questions here that you can use (or I may use on you if we meet!).

• What superpowers would you like to have?
• What activities provide you with pure joy?
• What are your passion projects that you would like to pursue?
• What self-care habits do you practice regularly?
• What are some of your personal habits that are important to you and why?
• What is the one dream for your life you most look forward to having come true?
• What would be the title of the movie or book if it was based on your life?
• If you had three wishes, what would they be?
• What is the most spontaneous thing you have ever done?
• What is your most favorite activity to do on your day off?
• They say life is about simple pleasures, what is your simplest pleasure, and how does it make you feel?
• If you could change one thing about yourself, what would it be?
• If you could change anything about the way you were raised, what would it be?
• Which fears would you like to remove from your life?
• What key lessons did you learn from your challenging times or failures?
• What do you like the best and least about your life right now?
• Looking back on your life, of what are you most proud?
• How often do you reflect on your current life and how to improve it?
• Looking back at your life, describe one particular event that you wish you had handled differently.
• What is the best advice you have received from others? Which advice would you give to your younger self?
• Whom do you admire most and how does this individual inspire you?
• Given the choice of anyone, dead or alive, whom would you want as your dinner guest? As a close friend? As a mentor?
• Which relationships (e.g. colleagues, old friends, etc) do you wish to improve and how?
• How would you use 1 million dollars to make this society better?
• How would you change the educational system?
• What is your favorite joke to tell others?
• If you can travel to the past or future, which year would you like to go and why?
• For an all-expense paid one-month vacation anywhere in the world, which country would you go and what would you do there?
• If you were offered 1 million dollars to live alone remotely on an island with no technology (ie. cell phones, laptop, wifi, data plan) for 3 months, would you do it?

REFERENCE

[1] The Book of Questions by Gregory Stock