What is something you're coming to realize?

If you could have dinner with any person, living or deceased, who would it be and why?

What is your most terrible memory?

What is your best advice on how to apologize?

What was your relationship like with your siblings growing up? If you didn't have them, who did you spend a lot of time with?

What's something you'd like to do, but have a hard time acting on?

How do you feel about your relationship with your father?

How would you describe your approach to your career so far?

Is there anything you think the previous generation did better than your generation?

What's an interesting conversation you recently had?

What is the hardest way you’ve learned an important lesson?

What life experience has shaped you the most, and in what way?

What elements of your daily routine have become non-negotiable lately?

What's something you've recently let go of, and how has it impacted you?

What's a significant change you're considering or have made?

What was your parents' relationship like?

Imagine you woke up with the ability to speak every language fluently; how would you use this power first?

Which form of self-expression has become increasingly important to you?

What's your favorite way to relax these days?

You can impart one understanding about human relationships to your child. What insight do you choose to share?

What were some of my most challenging learning moments in your career, and what made them so?

What's your most common feeling lately?

What do you think is your biggest strength and your biggest weakness?

What's an unpopular or controversial opinion that you hold?

In what ways do you think hardship can contribute to personal growth?

What are 3 things you love about yourself?

Do you have any biases you're aware of?

What's your least favorite part of your job and why?

How has your perspective on your career changed over time?

What is the greatest physical pain you've ever felt?

What's a deep or difficult question you've been pondering lately?

If you could start your own charity, what would it focus on?

Is there something you wish everybody knew about you without you having to tell them?

If you could have any mythical creature as a pet, which one would you choose?

What or who do you have an unhealthy relationship with?

Can you share an unexpected goal you have for this year?

What's a habit you picked up as a child that you wish you hadn't?

How much of your decision to stay in your current job is influenced by comfort and fear versus ambition and fulfillment?

What advice would you give to your teenage self?

If you could teach someone just one thing about how to be in a good relationship, what would it be?

What is something other people admire about you?

If you could learn one secret from anyone, who would it be and what would it pertain to?

What's a new hobby or activity you've tried recently?

After death, you can roam the universe and observe anything you want for all eternity, but never interact with anyone or anything. Or, you can cease to exist. Which would you choose?

What's the most challenging thing you're working through these days?

In three words, how would your family and friends describe you?

Some historical figures have epithets attached to their names (e.g. Alexandar The Great, or Michael Jackson: King of Pop). What would you like yours to be?

Is there anything you think the next generation will do better than your generation?

What's an ethical dilemma that keeps you up at night?

In what ways are you similar to your parents? In what ways are you different?

If you could pick up a new skill in an instant, what would it be?

What is your most regretful purchase?

What’s a mantra or affirmation you resonate with right now?

To what degree do you modify your behavior based on who you're with? Do you think this is good or bad?

What's the best advice you've ever received?

Did your household ever have a cooking disaster, or a meal that turned out really badly one time?

You just inherited $10,000,000. How does your life change tomorrow?

Can you share an instance where your first impression of someone was completely wrong?

If you had the power to completely solve one social or political issue affecting the world today, which would you choose?

What thoughts distract you when you’re trying to get to sleep?

What actions, if taken, would make you proud of yourself a month from now, regardless of the outcome?

Who in life has inspired you the most?

What do you wish people would talk more about right now?

What's a movie you can watch over and over without ever getting tired of?

Where do you wish you had grown up?

What's something good that recently happened to you?

What skills or passions are you not currently utilizing in your job?

What's your philosophy in life?

What's a great piece of advice you recently received? Who was it from?

What boundary did you recently set that has improved your relationship with someone?

How do you prioritize your tasks when everything seems urgent?

What's the most exciting improvement you've been seeing in yourself recently?

What's something you're frequently complimented on?

What do you consider as red flags in a potential friendship?

Do you have an internal hunch about how you will die?

What's one of your biggest pet peeves?

What does your ideal/dream life look like?

What are the top three qualities of your ideal partner?

Does anybody beside yourself know your deepest secret? Do you ever intend to tell anyone?

What's a recent decision that was hard to make?

If you could change one thing about your childhood, what would it be?

What behaviors will you no longer accept in your relationships?

If you could intervene during any historic event, changing history, what would it be? How would things unfold differently?

How has your perspective on the world changed in the last five years?

Do you have a best year of your life? A worst?

Who has made a positive difference in your life recently?

What's a memorable lesson you've learned from a mistake you've made?

What song is 10/10 in your book, but no one has heard of it?

What’s one of your earliest memories of earning money?

How has your relationship with your parents changed as you've gotten older?

What person in your life do you most admire?

What do people think is hard but actually isnt?

Is there anything important you've been putting off? If so, why?

What did you learn about the concept of love from your parents? Is there anything you want to keep, or anything you want to let go?

You can only guarantee your child learns one life principle. What do you teach them?

What is your best season of the year? Why?

What's one way in which you're completely different from yourself 10 years ago?

What's that one thing you keep buying or doing even though you know it's unhealthy?

If all animals were the same size, what would win in a fight?

What instantly makes you think less of someone?