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Questions to Ask Anyone

People want to be heard. They want to share their stories. They want to be recognized. Connect on that level and you’ll have a friend for life.

And sometimes all it takes is one good question. Below are some questions that have helped me create those moments of connection:

If you could live to 200, what would be your reason to stay alive so long?

Do you consider yourself a religious person? Have you ever had a spiritual experience?

What does the first 60-90 mins of your day look like?

What is your unfair advantage?

What’s the best purchase you’ve made under 100 dollars this year?

How do you define success?

What’s the last thing that you have failed at?

What is something that you have changed your mind about in the last year?

What was the last thing that you asked for help on?

If I gave you a billion dollars, but told you that you couldn’t spend it on yourself, what would you do with it?

What’s one thing that you will spend lavishly on no matter what?

What has become more (or less) important to you as you have gotten older?

What is the biggest upside to being you?

If there’s a fire in your house, what do you take with you?

Who are your heroes?

Have you ever had a near death situation? What was going through your head?

Last meal?

Is there a book that changed your life?

What is the one thing you should probably get rid of, but you just can’t?

What do you miss about your childhood?

What goals would you have if you had one year left to live, but you couldn’t spend it with friends or family?

If you were just finishing high school, knowing what you know now, what would you do?


*These are not for a quick casual encounter. It’s for situations where you’ll be spending a chunk of time with someone. They would make for very strange pickup lines.

-Many of these questions are original, but not all.

-These are great questions to ask yourself! Try the dream diving method.

-I’m very open about reading them from a list: “I have a list of fun questions, you want to hear them?” Almost like a game.

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