Skip the small talk
cut right to the chase
Which question can you ask to find out the most about one person?
5 min read — Personal growth
Use these questions to kickstart inspiring, connecting, and entertaining conversations with new people and old friends.
I have had complete strangers open up and connect on a deeper and more meaningful level than I ever thought possible.
With reunited old friends these questions led to roaring laughter and bitter tears.
It's not everyones cup of tea to connect meaningfully—be mindful and respect boundaries.
Level 1
–Starters
–What simple thing still blows your mind?
–What was the last thing you fell in love with?
–What piece of clothing best describes your personality?
–Which of your personality traits has been the most useful?
–What sparked your curiosity in whatever you're interested in now?
–When did you last feel unbound optimism?
–What is your one piece of advice to everyone here?
–Who was the last person you felt inspired by?
–What taste do you have that most people don't have?
–Which fictional character would be the most boring to really meet?
–What's the closest thing to real magic that you understand?
–What do you want your epitaph to be?
–There are two types of people in this world, what're the two types?
–Who is/was your most interesting friend?
Level 2
–Deep shit
–What do you miss most about your past that could be recreated today?
–What's the most important thing to remember daily that you haven't been able to achieve?
–Why are some people so addictive?
–What is the best measurement how an idea is absorbed into a culture?
–Which tasks would you keep to yourself—because you like them—if you could delegate all other tasks to robots that can perform them better, faster and more efficient?
–What's the most useful concept you are applying in your life that doesn't have a name?
–What's something you believe—but can't defend?
–What unwritten rules have you learned as a kid and are any of them outdated now?
–What was your most radical change of mind, what triggered the thought process?
–What small gesture from a stranger made a long lasting impression on you–and why?
Level 3
–only for close friends
–What do you think you're most likely to regret on your deathbed?
–Do you think you are undervalued as a person—if so—why?
–What are three of the most significant numbers in your life?
–If you had a clock that could count down to any one event in your life, what event would you want the clock to count down?
–What help could you most use that you haven't asked for?
–If you would get picked up by aliens in 10 minutes, what would be your last words and to whom?
–What is your most radical belief?
–If you could know the absolute and total truth about one question, what question would it be?
–What are you certain you'll never experience? What would you sacrifice to make it happen?
I’ve been running an experiment where I ask people at last one of these questions to understand their thinking and personality better.