14 More Questions to Deepen a Relationship

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In a recent post, I suggested eight questions to ask and answer that can deepen a relationship, romantic or platonic, perhaps even between a parent and an adult child.

That has turned out to be among my more popular posts, so here are 14 more such questions.

The previous set of questions was broadly applicable. Of the following, the first eight are especially well-suited to people who like to ask and answer personally probing questions. The second six are for people who like intellectual questions.

Of course, you won't want to ask a lot of these in one conversation, if ever. This is just a master list to draw from. Start with one question, listen carefully to the response—verbal and nonverbal—and proceed accordingly.

Personally probing questions

These questions are increasingly personal, so in a new relationship, you might want to try one of the first two before considering whether to try one or more of the others.

• Is there anything you believe that goes against the grain of conventional wisdom?
• What do you want? What do you really want?
• Is there something you’re embarrassed about having done that you’re willing to share with me?
• If you were giving a one-minute talk to your identical twin about sex, what would you say?
• What are you most scared of?
• What are you most insecure about?
• Have you ever thought about committing a felony, even if you'd never actually do it?
• What's a personally probing question you'd like to ask me?

Intellectual questions

These questions are presented in the order that would likely yield the most interesting answer. But, depending on whom you’re speaking with, you might want to start with a question that’s further down the list.

• What’s your definition of a life well led?
• What’s your philosophy of work?
• What’s your philosophy of health?
• Capitalism leads to net good but yields too many big losers. Socialism reduces destitution but inhibits competition and the desire to produce and to innovate. Does that argue for a mixed economy?
• Is the world better served if most of its populace believes in God as traditionally defined: an omniscient, omnipotent, benevolent deity?
• What’s an intellectual question you’d like to ask me?

I read this aloud on YouTube.