I’ve found that if I’m having trouble connecting with someone its usually my fault for not asking probing enough questions.

The people that I don’t like at first blush become much more interesting when you ask them questions like:

1. Whats your story?

2. What do you care about?

3. Personal questions about family, past relationships and best or worst experiences.

4. Not a question per say, but sharing your vulnerabilities and admitting flaws and weaknesses will lead others to do the same. And it’ll lead to a much more meaningful conversation and relationship.

5. Follow up questions that seem awkward.

To be fair, if the response is disingenuous or not truthful the negative perception may remain. But, hopefully this leads to a deeper vulnerable conversation about universal shared aspirations, fears and challenges. If it does, you will come away with a new appreciation for each other. You’ll learn something new about life and will be better equipped to be happy.

^Day 25/90 165 Words

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