An Indulgence: Which of the 36 questions are exceptionally revealing about people?

I am six (official) interviews into my thirty-six questions experience. When broken into three sets of twelve, one can see how the thirty-six become progressively intimate in their topic. I’m going to go through the three sets and talk about one from each which stands out in its ability to connect people. So if you’re at a party and looking for some great conversation starters- here they are!

From Set One:

9. For what in your life do you feel most grateful?

2Out of these twelve, number nine has always stood out. Why? We rarely stop today to think about what we are grateful for, and asking someone to find what they are MOST grateful for allows both of you to take that opportunity to find what is meaningful in your life. This question also reveals what it is the other person values without asking something they might hesitate to talk about.

From Set Two:

20. What does friendship mean to you?

This is another question that has a subtle way of providing insight about someone’s deeper values without seemingly enroaching on a topic typically considered a no-no socially.

From Set Three:

26. Complete this sentence: “I wish I had someone with whom I could share … “

I love this one because every answer is so unique. After having asked more than thirty people this question (both within the blog subjects and others I meet) I have never heard the same answer twice- and each person views the question in a different context. I have gotten answers that range from “my eating disorders and how they affect my life” to “debauchery- the pursuit of engaging in forbidden activities” to “my unparalleled love for ice cream”

There you have it. The three best questions to pull out next time you meet someone supremely interesting!

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Originally published at on January 24, 2016.

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