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You Asked for it: My List of Awesome Questions to Start Conversations

We began a message series at Mountain this weekend called THE JESUS QUESTION. I used to think Jesus was the…

post by Ben Cachiaras

We began a message series at Mountain this weekend called THE JESUS QUESTION.

I used to think Jesus was the guy with all the answers. Turns out Jesus has lots of questions. Jesus is really good at asking questions.

The right question at the right time has a way of making you think, engaging your heart, penetrating your stony heart – in a way that telling never does.

So Jesus, the One who knows it all, instead of telling us the answers, asks us questions.

We often ask questions because we want information for ourselves. Jesus asks questions because he wants transformation for someone else.

No wonder scripture records over 300 questions Jesus asked.

In the message, which you can catch here we talked about how counselors, parents, and friends can connect more deeply when we learn to engage in what Edgar Shien calls “the fine art of drawing another out.”

And the best way to do that is by asking questions.

In the message, I shared that I carry questions on my phone which we have used with our family on road trips. I told how it has helped my daughter Ellie and I connect with some great heart-to-heart conversations. Several have asked for that list of questions. I’m happy to share, in hopes you might cut and paste them into your own phone, and use some of them to draw out those around you, honor them by listening, and help family and friends connect better.

Here are the questions I shared in the message. Try one of these over a meal today:

This little book has a bunch more great questions, many which can open up spiritual conversations.

Some are warm up questions, like

And some dig a little deeper, like

And some that truly probe, like

I’ll never forget a night on the porch with friends a couple years back. Karla and I were with three other couples, all close friends whom we care about very much. It was a great evening around the fire pit, nice conversation and friendly chatting. But then my friend Greg pulled out  his phone and said, “I’ve got some questions here. Anybody up for using these to talk about stuff?” We dove in. And it totally changed the evening, and I am not exaggerating when I say it totally changed our friendship. We all remember that night.

I don’t recall the exact questions we talked through, but here is the list we drew from, by Arthur Aron (slightly edited by me to bring in a spiritual dimension). Paste them into your phone and use them at the dinner table, a car ride, or at your next small group or family gathering. Just pick a number between 1 and 28 and off you go.

  1. Given the choice of anyone in the world, whom would you want as a dinner guest?
  2. Would you like to be famous? In what way?
  3. Before making a telephone call, do you ever rehearse what you are going to say? Why?
  4. What would constitute a “perfect” day for you?
  5. When did you last sing to yourself? To someone else? What song?
  6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
  7. Name three things you and your partner appear to have in common.
  8. For what in your life do you feel most grateful? How regularly do you express thanks to God for it?
  9. If you could change anything about the way you were raised, what would it be?
  10. If you could wake up tomorrow having gained any one quality or ability, what would it be? What is a God-given quality or ability you are most thankful for?
  11. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?
  12. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  13. What is the greatest accomplishment of your life?
  14. What do you value most in a friendship?
  15. What is your most treasured memory?
  16. What is your most terrible memory?
  17. What does friendship mean to you?
  18. What roles do love and affection play in your life?
  19. How close and warm is your family? Do you feel your childhood was happier than most other people’s?
  20. Complete this sentence: “I wish I had someone with whom I could share…”
  21. If you were going to become a close friend with your partner, please share what would be important for him or her to know.
  22. Tell what you like about your partner/family. Be honest, saying things that you might not say to someone you’ve just met.
  23. Share an embarrassing moment in your life.
  24. When did you last cry in front of another person? By yourself? Would you like to share what it was about?
  25. What would you most like people to remember you for when you die?
  26. What are three things you love about your partner/family?
  27. What, if anything, is too serious to be joked about?
  28. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
  1. What are the things that most inhibit or harm your relationship with God at this point in your life?

Ask away.

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