70 Questions for Truly Getting to Know the People You Love
The provocateur of the weekly Sunday Questions series, I sincerely believe that there is no better way to connect with the people you love, and the people who love you, than asking them questions and truly listening to their answers.
Ever since I wrote a piece referencing the infamous “road trip questions” last winter, I’ve gotten dozens of texts from friends asking if I have a list of questions that they can share with their friends or family, and nothing makes me happier than knowing that a trait as accessible as curiosity can bring people together in such a simple way. These questions are free entertainment, free therapy, and one of the only things that can actually make a road trip exciting between bathroom breaks and are we there yet?’s.
For nearly two years, I’ve been relying on two lists of questions to spark these quasi interviews, most of which I have memorized through playing road trip questions with pretty much anyone in my vicinity. The two lists I’ve used and gained inspiration from are the New York Times 36 Questions to Fall in Love which I highly recommend for anyone seeking depth in their relationship (be it friendship, or romantic) and the much lighter 101 Fun and Random Road Trip Questions to Ask Your Friends which is where I got my leading, incredibly probing “what is your favorite donut?” question.
Going through the many questions that I’ve found on the internet has, of course, deepened my relationship and understanding of self, but far more importantly, it has shifted the relationships in my life tremendously. Asking these questions from a place of true curiosity creates a channel of trust and openness that fosters an immense amount of love, compassion, and understanding in any friendship or relationship. Whether you’re doing these questions with your partner, your parent, your friends, or someone you’ve just met, you will witness the connecting power of curiosity as you engage in the conversations that these questions create.
As they say, to be known is to be loved, and often we think we know the people in our lives much better than we actually do. Which brings me to the reason why I created a question set of my own: the more you get to know the people you love, the more you really see them as someone with far more depth and history than you’ve ever understood, and in turn, you develop a stronger, deeper sense of love and compassion for the person you’re connecting with. So the reason I’ve created these questions is really quite simple: for all of us to connect more, and learn to love each other better.
There are no rules for the 70 Questions for Truly Getting to Know the People You Love. Use them whenever, wherever, with whoever, in whatever order you please, and watch as beautiful, exciting conversations flourish around you. Cheers to being curious, and cheers to connecting more.
Love you all,
Cail
70 Questions for Truly Getting to Know the People You Love
What’s your favorite donut?
If you could have dinner with anyone in the world, dead or living, who would it be?
Share your top 5 artists/bands.
Do you drink coffee in the morning? If so, how do you take it?
What day of the week is your favorite and why?
What’s your favorite breakfast diner order?
If you had to live in a different state/country, where would you live?
What hobby would you get into if time and money weren’t an issue?
What does a perfect day look like for you? (From morning to evening. Where would you be? What would you eat? Who would be there?)
What’s your love language? Is how you like to give love different than how you like to receive it?
Would you say you have a sweet tooth?
If you could pick any brand to go on a trip with, what brand would it be?
Favorite movies in these four genres: comedy, drama, horror, Disney.
If you were on death row, what would your final meal be?
Where is the creepiest place you’ve ever been?
Do you have a hidden talent? If so, what is it?
Which of your scars has the best story behind it?
What’s your favorite book?
What’s one food you refuse to eat?
What is your favorite account that you follow on social media?
Would you ever want to be famous? If so, in what way?
What’s the best thing that’s ever happened to you?
What’s the worst thing that’s ever happened to you?
If you had to get a tattoo, what would it be and where?
What’s the most beautiful place you’ve ever been?
What do you think your most dominant character trait is?
If you could travel anywhere in the world, where would you go?
What’s your biggest fear?
What’s the best compliment you’ve ever received?
What are 5 activities/things that spark joy for you?
If you knew that you were going to die one year from now, how would your life change? What would you do?
Is there someone you love/once loved who doesn’t know you feel/felt about them?What held you back from telling them?
What’s the worst sunburn you’ve ever gotten?
What is one thing on your bucket list?
What’s the best piece of advice you’ve ever gotten?
For what in your life do you feel the most grateful?
Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
What do you most value in a friendship?
Think of the people you love most in your life. What traits of theirs would you like to embody?
What is your most treasured memory?
What’s the dumbest thing you’ve ever done and what, if anything, did you learn from it?
What’s a trait you have that you’ve learned to love?
Would you consider yourself an affectionate person?
How important is privacy to you?
How do you feel about your relationship with your family?
What do you believe are your core values?
What do you think other people might misunderstand about you?
Tell each other something you admire about one another.
What, if anything, is too serious to be joked about?
What is a memory that you try to avoid thinking about?
If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven't you told them yet?
When in your life did something not go according to plan but work out in your favor?
Who are the people in your life that you feel most yourself around?
What is taking up most of your brain space currently? Is anything weighing on you/exciting you?
What’s your relationship with physical intimacy like?
How often do you say “I love you” to the people in your life?
What’s a deal breaker in a friendship for you?
What’s a deal breaker in a romantic relationship for you?
Describe your ideal partner. What are they like? What traits do they possess? What is your relationship like?
What are three free activities that bring you joy?
What’s your favorite physical attribute about yourself?
What is your relationship with your body like?
What part of your body/appearance do you feel like needs more love from you?
What’s your dream job?
Do you feel like you know your purpose? If so, what is it?
How different was your life one year ago?
If you had to pick a mantra for the next year of your life, what would it be?
Do you want to have kids?
If you raised a family, where would you want to raise them/what kind of parent would you want to be?
Tell the person you’re doing these questions with something that you think is beautiful about them.