60+ Thought-Provoking Questions To Ask Yourself, Your Friends & More

Originally published @ MindBodyGreen

By Sarah Regan

- Content and imagery reposted with permission -

In the flurries of small talk and day-to-day happenings, sometimes we don’t take the opportunity to dig deep and really ask people (ourselves included) deeper, more thought-provoking questions. But it’s often those deeper questions that help us really get to know someone and learn more about the people in our lives. Plus, they can lead to some pretty interesting conversations. So, we rounded up over 60 expert-approved questions to ask anyone and everyone in your life.

How thought-provoking conversations help deepen relationships.

Thought-provoking questions and conversations are all about curiosity and connection, according to somatic psychologist and therapist Holly Richmond, Ph.D., LMFT, CST. “Conversation—not a monologue—is a direct route to someone’s head or heart, depending on the context,” she explains. When you ask someone quality questions—and show genuine interest in what they have to say—”you set up a system for a deeper connection going forward.”

And according to licensed marriage and family therapist Tiana Leeds, M.A., LMFT, without touching on these deeper topics, we’re left with our own assumptions about others, which, of course, aren’t always accurate.

“Conversation is our shortcut to understanding who someone is and deepening our connection to them,” she explains, adding that open communication can give us direct access to someone’s innermost thoughts and feelings—and also gives us the opportunity to be seen and known. As Richmond notes, good conversation is all about reciprocity.

Questions to ask yourself:

  • What is my intention here?
  • What are my core values?
  • Which of my deep inner longings have I been ignoring?
  • Who lights me up when I’m around them?
  • Who drains my energy when I’m around them?
  • When do I feel most alive?
  • What am I feeling—nervous, anxious, trepidatious, excited, eager—and what is making me feel that way?
  • How do I honor myself? Neglect myself?
  • How have I grown as a person?

Deep questions for new friends:

  • What’s been on your mind today?
  • What are you excited about right now?
  • Is there anything you’re worried about?
  • How connected are you feeling to the world?
  • What are you passionate about?
  • What do you value most in a friend?
  • What consistently brings you joy right now?
  • What feels hard in your life right now?
  • Is there a decision you’re contemplating that would be helpful to talk through together?
  • What’s bringing you pleasure right now?
  • What’s something difficult you’re working on?

Questions to ask a romantic partner:

  • What feeling have you been experiencing the most lately?
  • How connected are you feeling in our relationship?
  • Are you sexually fulfilled?
  • What could make our relationship even better?
  • What makes you feel most loved?
  • Is there something you care about for which you would be willing to risk your life?
  • How can I be a better partner to you?
  • What were you like as a child? As a teen?
  • Tell me about the last time you felt lonely when you were with me.
  • What are your dreams for your future?
  • What makes you feel closest to me?
  • Is there anything you are grappling with where I can help?
  • What is your vision for a great relationship?

Thoughtful questions for family members:

  • What excited you today?
  • What are you feeling grateful for today?
  • What was missing from your life this week?
  • About what have you been proud of yourself for this week?
  • What are you eager to feel more confident about in the next few weeks?
  • What word would you use to describe our family?
  • Do you identify with our family, or do you feel more like an outsider, and why?
  • What family traditions do you carry on?
  • Tell me about a time you did something you “weren’t supposed to” but it was worth it.
  • Tell me about a family member of ours who I never had the chance to meet.
  • What are our strengths as a family?
  • What is your favorite present you’ve ever received?
  • What are our values as a family?
  • Any traditions that you were happy to say goodbye to?
  • What do you think our family will look like in 50 years?

Philosophical questions:

  • Where are you finding the most meaning in life?
  • What do you imagine your legacy will be?
  • How long do you think you’ll be remembered?
  • What do you feel has been the most important thing you’ve done in life so far?
  • What lasting impact do you know you’ve made in the world?
  • What’s the most important quality a person can have?
  • What does the world need more of?
  • What does the world need less of?
  • Do you think the sciences or art will be valued more in the next 50 years?
  • Why is art important or unimportant?
  • Will organized religion have a bigger or smaller place in society going forward?
  • What is the meaning of happiness?
  • Do you place a bigger value on helping yourself, your family, or the world? How so?
  • By what standards do you think society should be judged?
  • Do you feel like the world is changing for the better or changing for the worse?
  • How so?
  • Is there a motto or principle you live by?
  • Is morality relative?
  • What from the past is worth preserving?
  • In what ways has society changed during your lifetime? What do you think caused these changes?
  • Is it better to be realistic or optimistic?

The takeaway.

From being a good friend or partner to simply knowing how to keep a good conversation going, having an arsenal of thought-provoking questions is always helpful. Not only can you exchange interesting and new ideas, but you learn more about the people in your life, they learn more about you, and you’re able to deepen and strengthen your connection and understanding between each other, whether they be a friend, family member, or partner.


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