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Prompts
Marriage Conversations
What’s your favorite aspect of our relationship?
When you think about our relationship, how do you describe it?
What movie reminds you of me?
What advice do you have for your future self?
What do you remember most about your teenage years?
What qualities do you love about yourself?
What song reminds you of our love?
What characteristics of fairytales resonate with you the most?
When you imagine our life in 30 years, what’s it like?
What aspect of our relationship needs a makeover?
When you think about your parents, how do you describe them?
What’s your favorite date night activity?
What about our relationship excites you the most?
What characteristics do you share with our children?
What’s made our relationship successful thus far?
What memories in life gave you a run for your money?
What are your favorite qualities about our relationship?
Which famous couple reminds you of us?
What’s your biggest fear in life lately?
What legacy do you want to leave?
What do you remember about the first time we met?
What is your favorite memory together?
What song reminds you of us?
What aspects of our relationship should be more intentional?
What has been the best date so far?
What have you learned about yourself since being together?
What hobbies and talents have you discovered since being together?
If you could relive any day of your life. which would it be?
What can we do to show more love?
What aspect of our relationship makes you the proudest?
What secret ingredient makes love last?
What moments taught you the biggest life lessons?
What advice would you give to your younger self?
Which anniversary was your favorite?
What were your top three spontaneous date nights?
Would you rather travel to 20 years ago or 20 years from now?
What events and activities can we add to our bucket list?
What family tradition do you hope continues to future generations?
Family Conversations
What’s your least favorite snack?
If you could create season what would it be like?
If you could be in any movie or show, what would it be?
What brings you the most pride?
What’s brightens your day when you’re feeling sad?
What similarities do you share with your sibling(s)?
If you could plan a family vacation, where would we go?
What is your favorite family tradition?
What aspect of school do you love the most?
If you could create your dream job, what would it be?
Which family member do you share the most similarities with?
What toy or item from now do you wish to keep forever?
What’s the nicest thing someone’s ever said to you?
If you could change one aspect of school, what would it be?
What’s your favorite family recipe?
What outing or gathering is the most special to you?
Would you rather travel to 100 years ago or 100 years from now?
What’s been your favorite school subject or topic so far?
What book has taught you an important lesson?
What’s your favorite part of summer?
What aspect of life do you appreciate the most?
Where’s your favorite reading/chilling place in the house?
What similarities and differences do we have?
What do you imagine your life to be like in 20 years?
What childhood memory do you remember the most?
What’s your dream job?
What advice would you give to your future self?
What has been your proudest moment so far?
If you could change one thing about your life, what would it be?
Where were you born?
What was your childhood like?
What was your favorite subject in school?
What games did you like to play as a child?
What did you want to be when you grew up?
What family traditions did you have growing up?
What are some new family traditions in our family?
What’s the most important thing you learned from your parents?
If you could travel back in time, when would you travel to?
What’s one thing you want me to remember forever?
Would you rather have a mountain house or a beach house?
If our family had a theme song, what song would it be?”
Friendship Conversations
What’s your favorite aspect of our relationship?
When you think about our relationship, how do you describe it?
What movie reminds you of me?
What advice do you have for your future self?
What do you remember most about your teenage years?
What qualities do you love about yourself?
What song reminds you of our love?
What characteristics of fairytales resonate with you the most?
When you imagine our life in 30 years, what’s it like?
What aspect of our relationship needs a makeover?
When you think about your parents, how do you describe them?
What about our relationship excites you the most?
What characteristics do you share with our children?
What’s made your relationship successful thus far?
What memories in life gave you a run for your money?
What are your favorite qualities about our relationship?
Which celebrity friendship reminds you of us?
What’s your biggest fear in life lately?
What legacy do you want to leave?
What do you remember about the first time we met?
What is your favorite memory together?
What song reminds you of us?
What aspects of our relationship should be more intentional?
What has been the best adventure we’ve had so far?
What have you learned about yourself since we met?
If you could relive any day of your life. which would it be?
What can we do to show more love?
What aspect of our friendship makes you the proudest?
What secret ingredient makes love last?
What moments taught you the biggest life lessons?
What advice would you give to your younger self?
What’s your favorite date night activity?
Which anniversary was your favorite?
What were your top three spontaneous date nights?
Would you rather travel to 20 years ago or 20 years from now?
What events and activities can we add to our bucket list?
What family traditions of yours do you hope continues to future generations?
What would be the top 3 items on our friendship bucket lists?
What is your favorite vacation we’ve taken together?
Would you rather have a mountain house or a beach house?
What is the funniest joke you know?
If you had to lose one of your five senses, which one would you want it to be?
Sibling Conversations
What’s your favorite part of summer?
What aspect of life do you appreciate the most?
Where’s your favorite reading/chilling place in the house?
What similarities and differences do we have?
What do you imagine your life to be like in 20 years?
What childhood memory do you remember the most?
What’s your dream job?
What advice would you give to your future self?
What has been your proudest moment so far?
If you could change one thing about your life, what would it be?
If you could create your dream job, what would it be?
Which family member do you share the most similarities with?
What toy or item from now do you wish to keep forever?
What’s the nicest thing someone’s ever said to you?
If you could change one aspect of school, what would it be?
What’s your favorite family recipe?
What outing or gathering is the most special to you?
Would you rather travel to 100 years ago or 100 years from now?
What’s been your favorite school subject or topic so far?
What book has taught you an important lesson?
What’s your least favorite snack?
If you could create season what would it be like?
If you could be in any movie or show, what would it be?
What brings you the most pride?
What’s brightens your day when you’re feeling sad?
What similarities do you share with your sibling(s)?
If you could plan a family vacation, where would we go?
What is your favorite family tradition?
What aspect of school do you love the most?
What is your biggest childhood secret you never told mom or dad?
Would you rather have a mountain house or a beach house?
If you could have any superpower, what would it be and why?
What is your least favorite chore?
If you could only eat one thing for the rest of your life, what would it be?
What was your favorite dinner to eat growing up?
What would you have named yourself if you could have chosen your own name?
What do you do to get yourself out of a bad mood?
What is the funniest joke you know?
If you could trade places with your parent for a day, what would you do differently?
Co-Corker Conversations
What’s your favorite hour of the workday?
If you could remove one work-related responsibility, what would it be?
What excites you the most about your job?
What significant changes have you seen in company culture lately?
Who is your favorite informal mentor?
If you weren’t working in this position, where would you be?
How would you react to a 400% pay increase?
What’s your favorite mid-day snack?
What songs or artists do you play when you need a pick-me-up?
What advice would you give to someone starting their career?
If you had to lose one of your five senses, which one would you want it to be?
If you could trade lives with someone famous for a week, who would it be?
What has been the happiest day of your life so far?
What is your hidden talent?
What book would you recommend to your friends?
What do you do to get rid of stress?
What would be your perfect weekend?
When was the last time you worked incredibly hard?
If you opened a business, what kind of business would it be?
Are you a very organized person?
Have you ever given a presentation in front of a large group of people? How did it go?
If you had to change your name, what would your new name be?
What is the silliest fear you have?
What are some things you want to accomplish before you die?
What is the best room in your house? Why?
Elder Generations Conversations
What is one invention you wish existed?
Where were you born?
What was your childhood like?
What was your favorite subject in school?
What games did you like to play as a child?
What did you want to be when you grew up?
What family traditions did you have growing up?
What are some new family traditions in our family?
If you could travel back in time, when would you travel to?
What’s one thing you want me to remember forever?
What do you know about our family history?
What’s the most important thing you’ve learned from your parents?
What’s your favorite thing about being a grandparent?
What is the secret to handling stress?
What would I be surprised to learn about you?
How has your life changed since becoming a grandparent?
Where was the most interesting place you’ve traveled?
What’s are some of your favorite childhood memories?
What considerations should I have regarding becoming a parent?
What message would you like to give my grandchildren?
Describe your idea of the perfect day.
What book would you recommend to your friends?
What are your top 5 favorite movies of all time?
How did you choose your children’s (or pets’) names?
What’s something you did that was embarrassing at the time, but you now see the humor in?
What’s your number one piece of life advice?
What world events had the most impact on you?
Do you remember any trends from your youth? Popular hairstyles? Clothing?
Did you receive an allowance as a child? How much? Did you save your money or spend it?