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Patrick Reynolds

Get to Know You Questions

A running list of questions I like for getting to know someone, grouped by theme.

Childhood

  • Where were you born and where did you grow up?
  • How would your parents or teachers have described you as a kid?
  • What did you do for fun when you were by yourself?
  • Who did you look up to?
  • What did you want to be when you grew up?
  • What was a turning point or defining moment in your childhood?

School

  • What was your favorite subject in high school or earlier?
  • Where did you go to college? Why?
  • What did you study? Why?
  • What was your favorite non-major class? Why?
  • Did you enjoy your college experience?
  • Would you send your kids to college?

Family

  • How many siblings do you have, where do you fall in the order, and how close are you?
  • What are your parents like, and what is their relationship like?
  • In what ways are you more like your mom, and in what ways more like your dad?
  • What role did you play in your family growing up?
  • What stories get told and retold in your family?
  • How close are you with your family now compared to growing up?

Hobbies

  • What do you spend most of your free time on these days?
  • What makes you lose track of time?
  • Is there a hobby you take seriously enough that it feels like part of who you are?
  • Is there something you used to love doing that you've stopped? Why?
  • What do you enjoy doing most with friends?
  • What do you enjoy doing most with your partner?

Favorites

  • Favorite cuisine?
  • Favorite genre of music or artist?
  • Favorite movie or show?
  • Favorite book?
  • Favorite place you've traveled?
  • Morning person or night owl?

Personal

  • Do you believe in personality tests? If so, what's your Myers-Briggs, Enneagram, and Big Five (OCEAN)?
  • What are the values you try hardest to live by?
  • When you make a big decision, do you lead more with your head or your heart?
  • How do you handle stress and hard emotions?
  • What's a belief or opinion you've meaningfully changed your mind about?
  • Do you consider yourself spiritual or religious, and where do you find meaning?

Career

  • For each past role:
    • How did you find it?
    • Why did you choose it?
    • What did you enjoy most about it?
    • What did you enjoy least about it?
    • What accomplishments are you most proud of?
    • What were some low points?
    • Why did you leave?
  • Rank what you want most out of work: impact, mastery, money, autonomy, recognition, or something else.
  • How do you define success, and has that definition changed over time?
  • What are you working toward right now, and where do you hope it leads?
  • When are you at your best at work, and what kind of environment brings that out of you?
  • What other careers could you see yourself in, in a parallel universe?

Siblings

For two siblings to ask each other.

  • What is your favorite memory of us?
  • What is your favorite game or activity we used to play together as kids?
  • Do you remember any funny or embarrassing moments from our childhood that still make you laugh?
  • What's something you got away with as a kid?
  • What childhood memory do you think about often?
  • Is there a particular family tradition or ritual that holds special meaning to you?
  • Are there any lessons or values you learned from our parents or family that have stuck with you?
  • How do you think our upbringing has influenced the people we are today?
  • What do you admire most about each other?
  • What's one thing you would change about our childhood?
  • Is there anything about our relationship you would like to change?
  • Is there something you'd like to say to me, but haven't known how to?
  • What do you hope our future looks like?
  • Is there a dream or goal that you've always wanted to pursue together?
  • How do you envision our relationship evolving as we grow older?