Conversation Starters/ Questions to become curious again

Conversation Starters

Questions to become curious again

Wishes

  • If you could have free, unlimited service for five years from an extremely good cook, chauffer, housekeeper, masseuse, or personal secretary, which would you choose?
  • Would you be willing to have horrible nightmares for a year if it would be rewarded with extraordinary wealth?
  • If you could relive one year of your life, what year would it be?
  • Describe the home you would like to design for yourself.
  • If you could have any view from your back porch, what would it be?
  • If you were given money to remodel your house, what would you change first?
  • If you had $500 what would you buy for fun for yourself? For a need for yourself? $5,000 $20,000? $200,00?
  • If you could make decisions for someone you love, what would you change?
  • What supplies would you get at an art store if you had free money? What ways do you enjoy being creative?
  • What famous person, dead or alive, would you like to have dinner with?
  • If you could have a superpower, which one would you pick?
  • What historical time period would you most like to visit?
  • If you could donate a million dollars to a charity, which would you choose or start?
  • “I wish….”
  • If you had to choose a new first name for yourself what would it be?
  • In what event would you most like to win an Olympic gold medal?
  • If you could win any competition in the world, what would it be?
  • If you could have front row seats to any concert or show, who would you like to see? Favorite already seen.
  • If you could find people like you with a very particular interest or personality, who would you like to find?
  • If you could choose to change one small thing in the world what would it be?
  • What 5 questions do you want to know the answer to?
  • What would you do if you had 2 extra hours to spare everyday?

Future

  • What medical breakthrough would you like to see in your lifetime?
  • What goal do you hope to accomplish this year? 
  • Where do you see yourself in 5 years? 10 years? 
  • What’s on your bucket list?
  • What do you think people will be nostalgic for in 50 years?

Fun

  • What would be a fun joke if you had an identical twin?
  • Who is the most joyful person you know?
  • Tell a funny joke you know.
  • Share a funny memory or something that made you laugh hard.
  • If you were to get a tattoo, what would you get?

Memories

  • What is a favorite something/collection of your childhood?
  • Share a special memory or event from childhood.
  • What childhood memories do you have playing outside/in nature?
  • When you were young, what did you want to be when you grew up?
  • How were you different when you were young?
  • What’s the weirdest/dumbest thing you’ve ever done?
  • What school subject was most difficult for you?
  • Who was your favorite teacher and why?
  • Share a time when you were really scared or did something scary.
  • What was your best Halloween costume?
  • Share a time when you laughed really, really hard.
  • What was your first time being a parent or pet parent like?

Favorites

  • TV shows/Movies
  • Books/Section of a bookstore/Authors
  • Podcasts/YouTube Channels
  • Social Media influencers
  • Online sites/Platforms
  • Color/Scent
  • Restaurants
  • Foods: Appetizer/Soup/Breakfast Meal/Cereal/Lunch or Dinner Meal/Dessert/Candy
  • Item that has made your life easier?
  • Vacation- you’ve been to or would like to go
  • Staycation- what would you do?
  • Exercise? Sport to play? Sport to watch? 
  • Gift received
  • “If I could have any animal in the world as a pet, it would be….”
  • Party game/Least favorite
  • Which of the following rides would be your first choice: Gondola in Venice? Cab in London? Ferrari on the autobahn? Hot air balloon in Switzerland? Airboat in the Everglades? Raft down the Colorado River? Carriage in Paris?
  • Best/worst purchase
  • 3 favorite things to do specific to this city?

Work

  • What is most important to you concerning a job?
  • If you had to work but didn’t need the money, what would you do?
  • What are the most stressful parts of your job? What are the most fun/satisfying parts of your job?

Selfhood

  • Best/hardest part of this week?
  • What 5 words would you use to describe yourself?
  • What is a risk that you took that you are really proud of?
  • What is something you wish you had said “yes” to?
  • What do you like most about your home?
  • What are 5 things you are thankful for besides your family/pets, friends and health?
  • If your partner/best friend wrote a book about you, what do you think it would be called?
  • If you wrote a book or gave a talk, what would it be about?
  • What are some values or beliefs you want people to take from watching you life your life?
  • When and where do you feel most relaxed and peaceful?
  • “I lose track of time when….”
  • What was the best day of the past week and what made it so?
  • Would you describe yourself more as an extrovert or introvert?
  • What is something about your ethnicity/heritage you think is neat or want to pass on?
  • What are some of your quirks/preferences unique to you (i.e. house rules, manners, etc)
  • What would you like to learn or read more about?
  • Would you rather be a great musician, athlete, scientist, artist, politician or writer? If you are already one of these, what would be your next choice?
  • If you had to spend one year living alone in a remote cabin, what would you spend your time doing?
  • Who are your role models/mentors?
  • Who do you sometimes compare yourself to?
  • What’s your proudest accomplishment?
  • Would you choose to be the worst player on winning team or the best player on a losing team?
  • What is something that most people enjoy but you don’t? 
  • What’s a controversial or surprising opinion you hold?
  • What would you like to do that you think it’s too late in life to do? 
  • What’s the most interesting thing you’ve read or seen this week?
  • What big question have you been pondering lately?
  • When is the last time you tried something new?
  • What do you wish you had started and spent more time doing five years ago?
  • What would you do different if you knew nobody would judge you?
  • We have many sides- when do you feel most at ease and in your most natural state?  
  • How have you changed in the last 5 years? Last year?
  • What are you most looking forward to this month?
  • What is something most people don’t know about you?
  • What has been on your mind this week?
  • What was the last thing you got angry about?
  •  What is your greatest strength and biggest weakness?
  • Are there any important dreams you’ve had while sleeping that you hold onto?
  • How would you like to be celebrated on your birthday or special holidays?
  • What is one of your bad habits or guilty pleasure?
  • What is something you will never do?
  • What are some things that drive you bananas? Pet peeves? Stresses you out?
  • What remains undone that you’ve wanted to get done for years?
  • What habit would you like to start?
  • What’s an embarrassing moment you can share?
  • If you could do something dangerous just once with no risk, what would you do?

Discussion

  • If you were a high school principal what is something you would do?
  • If you were president what is something you would do?
  • If you could change a law, what would you like to see changed?
  • What are some of the values your parents instilled in you?
  • Do you believe in God? Free Will? Something else?

Relationships

  • What are the characteristics of a good relationship or things you specifically look for?
  • If you are a parent, what would you most like to do if you weren’t? If you are not a parent, what part of being a parent do you think you would enjoy most?
  • Of the 6 Love Languages (gifts, acts of services, quality time, verbal affirmation, touch, and space) in which order do you think you want the most?
  • Describe an especially strong person you know.
  • Describe an especially kind person you know. 
  • Who/what do you miss?
  • What do you value about the personalities of each of your immediate family members?
  • Are you more of an introvert or extrovert? (An introvert mainly recharges by being alone/in quiet- it has nothing to do with being shy)
  • What are 5 things you haven’t shared that you would like to say out loud to someone if you could?
  • What is your definition of Love?
  • What are some of the nicest things that have been done for you?
  • What wish would you give to the people you care about if you could (e.g. best friend, family, partner, etc)?

Wisdom

  • What advice would you give a younger version of yourself?
  • What is some of the most helpful constructive criticism you received?
  • What are some of your favorite quotes or pieces of advice: On relationships? On work? On self? On life?
  • What is something you think every person should experience in their lifetime?
  • What or who could you pay more attention to in life?
  • What motivates you in life?
  • What lessons in life did you learn the hard way?
  • What are you sure about in your life or about life itself?
  • What is something you used to believe about love or life that you’ve learned otherwise?
  • Hardest change of your life/thing you’ve done?
  • What is something you wish you could do over?
  • Are you holding onto something that you need to let go of?
  • What are some of the hardest things about getting older? What are some of the best?
  • How do you want to be remembered when you are gone?