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A note from the author: These differ from some other lists of questions in that they are not all necessarily conversation starters. In fact, some of them could really make people feel uncomfortable if they’re not asked in the context of a relationship that really seeks to understand them and make them feel welcomed, received, and heard! Think of a beach on a cool morning: to acclimate, wade in first.

Remember: genuine conversation…

  • builds on our own authenticity and vulnerability
  • sets aside our own agendas
  • seeks real understanding
  • listens more than it responds
  • is patiently comfortable with others being “in process”, with silence, with deep emotion; it does not always seek to fix, advise, or solve
  • seeks to love the other person well—not meet our own needs to be known as a counselor or confidante, or to “win the other person over” divorced from compassion and concern
  • practices reflective listening
  • makes “charitable judgments”—assuming the best about someone until able to gather more information.  When tempted to pass judgment or criticize, instead presents (non-pointed) questions to understand

Now—let’s get to it!

  1. What are the top five things you’re most passionate about? Which ones are you able to give time and attention to in your current stage of life—and which ones are on the sidelines for now?
  2. Tell me the main events in your “story” that anyone who wanted to understand you—including where you came from and what makes you tick—would need to know.
  3. If you could describe yourself in five adjectives, what would they be? What are three adjectives that you sometimes wish you were, but you’re not?
  4. What’s the highest compliment you’ve ever received?
  5. When you’re at the end of your life, what would “success” look like for you?
  6. What do you most want or wish for that you haven’t (yet) seen realized? How do you deal with these “not yet’s” or “no’s” in your life—or what does it look like to still be wrestling through them?
  7. What’s God been doing in you lately?
  8. What would you say to ___ (person you’re in conflict with, or feeling misunderstood by) if you knew they would listen?
  9. How have you been seeing God around you lately?
  10. So it sounds like you’re saying ___. Do you feel like I’m getting you? Is that what you’re trying to say?

Like this post? Don’t miss 6 Ways to Take Your Relationships Deeper in 2016.

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