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 qualities are you attracted to that you wish you had?
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 did you admire about your teenage self?
What childhood memories do you have playing outside/in nature?
When you were young, what did you want to be when you grew up?
What are the ways you rebel- in your youth and now?
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.
Share a time when a stranger delighted you or made you feel loved.
What was your first time being a parent or pet-parent like?
What is a moment you would go back to that you really loved & wouldn’t change a thing about?
What is an ordinary place that feels extraordinary to you because of what happened there?
What’s an embarrassing moment you can share?
What was the most significant year of your life?
When has selfishness served you well?
What was your personal experience of COVID like (sad, bad, and/or positive)?
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 do you daydream about?
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?
Is there anything in your life that has felt pre-destined?
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?
Was there a bedrock truth that you later found out was not true?
How comfortable are you with silence?
Do you have a place or space that you find sacred?
If you could do something dangerous just once with no risk, what would you do?
What is something people think comes naturally to you but that actually takes a lot of work?
Does time feel like a positive or negative force in your life right now?
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)?
How do you stay connected to people you’ve lost?
What you are most afraid of at this point in your life?
Wisdom
What advice would you give a younger version of yourself?
What’s the biggest sacrifice you’ve ever made?
What is something you think about today very differently than you did 10yrs ago?
Is there a bedrock of truth that you have grown to find out is not true?
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 have you learned to be careful about?
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?
What is the hardest change you’ve made or thing you’ve done?
What is something you wish you could do over?
What is a major disappointment that turned out to be a blessing?
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?
How has your idea of what it means to be a good person changed over time?
