101 Thoughtful and Provoking Questions To Ask To Get To Know Someone

Excerpt: Looking for questions to ask to get to know someone? This list has you covered. Good for getting to know someone new or old, known or unknown, stranger or friend. Questions are the key to meaningful connection. Enjoy.

Click Here to jump right to our list of questions to ask to get to know someone!

Introduction: Questions Are The Key

I am semi-obsessed with questions. I think that questions are the ultimate mind hack. I think questions can help direct focus and productivity. I think questions can help you find your life path. I think that the people who ask the best questions are the ones who get the best answers and resultantly, get the best results in life. And, of course, I think that questions are the key to meaningful conversation and deeper connections—something we all crave and instinctually desire.

For, how better to get to know someone than by asking them better questions? Questions that get them to share who they are, what they think, how they feel, that go beyond the normal inquisition, and get them to express all that is going on inside of them that’s hidden from the naked eye? There are, as far as I can tell, but two ways to get to know a person for who they are on the inside—either by waiting and letting them express it themselves or by asking them the question(s) that get them to reveal the part of their insides that the question begets.

You can sit and wait, but I fear what you might find is more people hiding than spontaneously sharing. Which leaves your prompting. Questions are the secret. They are the key. They are the bread and butter of every good conversation. The only real question is, will you have the courage to ask? And, I suppose this is a real question, too, what will you ask when the opportunity is there? Enter our list of 101 thoughtful and provoking questions to ask to get to know someone.

I compiled for you below, 101 of the most amazing questions I could think of and find that would help prompt much more than a one or two word answer in reply. In fact, that’s really the key to all good questions—they’re framed in a way that allows space for explanation, elaboration, description, intrigue, challenge, and reflection. What’s even more interesting about this whole process, is that while the questions may remain the same, the answers will almost always differ—even when asked to the same person. For, we are not a stagnant, unchanging organisms. We are very much alive and constantly evolving, learning, changing, and experiencing new things.

So, this is not a list that is to be explored and marked as being completed. Rather, it’s a list that can be enjoyed today and enjoyed again tomorrow. These are questions that can be shared with a friend, with a lover, with a stranger, and back again with the same person again in the future. And, of course, there’s no format. You can answer only the ones that appeal to you. You can challenge yourself and/or the person you’re sharing this list with to answer all of them with you. Or you can pick randomly!

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Enjoy this list how you may. My hope, is that it will prompt dialog that goes much further than the usual exchange. We are so much more than one or two word answers. We are divine and infinitely complex being on the inside and conversation helps us unravel and make sense of that complexity. Let’s dive a little deeper into each other’s minds and unravel together. Let’s share some of our uniquenesses, insights, and vulnerabilities. Let’s go beyond the superficial and make some space for more of what’s real. Let’s start connecting more and hiding less. And, perhaps most importantly, let’s be the one who asks the first question. Good luck.