100 deep questions to ask

Light

What's something you've changed your mind about in the last few years?

Then ask: What finally tipped it: an argument, an experience or a person?

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Which ordinary skill do you wish you had learned earlier?

Then ask: What stopped you then, and is it still stopping you?

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What kind of problem do you enjoy working on, even when it's hard?

Then ask: Would being paid for it change how it feels?

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Where do you feel most like yourself?

Then ask: What does that place have that the rest of your week lacks?

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What's a small kindness from a stranger that you still remember?

Then ask: Have you ever done the same for someone else?

Light

Which piece of good advice do you keep ignoring?

Then ask: What would it cost you to start following it?

Light

Which question do people often ask you that's hard to answer honestly?

Then ask: What would the honest answer be?

Deeper

What do most people misunderstand about the work you do?

Then ask: Is there a part of it you've stopped trying to explain?

Deeper

Which of your opinions would surprise people who only know you casually?

Then ask: Why does it usually stay hidden?

Deeper

What do you believe mainly because of where you grew up?

Then ask: Raised somewhere else, which beliefs would you expect to hold instead?

Deeper

When did you last feel completely out of your depth?

Then ask: What did you do in the first ten minutes?

Deeper

What would you do with a year off that was fully paid for?

Then ask: Which part of that could you start without the year?

Deeper

What's the best argument against something you believe strongly?

Then ask: Have you ever said it out loud to someone who agrees with you?

Deeper

Who outside your family shaped you most, and did they know it?

Then ask: What would you tell them now?

Deepest

What do you hope people say about you after you've left the room?

Then ask: How close do you think the real version is?

Deepest

Which part of your life is going better than you usually admit?

Then ask: What makes it hard to say so?

Deepest

Which fear has made more of your decisions than you'd like?

Then ask: Name one decision it made for you.

Deepest

What would you attempt if nobody would ever learn whether you failed?

Then ask: Is it the failing that stops you, or being seen to fail?

Deepest

What are you proud of that nobody ever asks you about?

Then ask: Why do you think it never comes up?

Deepest

When have you been most wrong about a person?

Then ask: What did you miss, and what did you see that wasn't there?

Light

Which memory of us do you think about more often than I'd guess?

Then ask: Why do you think that one stuck?

Light

Which trip, meal or night out would you repeat exactly as it was?

Then ask: What made it work that we could never plan for?

Light

What did you think of me when we first met?

Then ask: Which first impression turned out to be right?

Light

What do you enjoy now that you'd have mocked ten years ago?

Then ask: What changed: you, or the thing?

Light

Which of your other friends do you think I'd get on with best?

Then ask: Why haven't we met yet?

Light

Which of my habits have you quietly picked up?

Then ask: Is there one you hope you haven't?

Light

What song would you choose as the soundtrack to this year so far?

Then ask: Which line in it is doing the work?

Deeper

What part of your life do you think I don't really see?

Then ask: What would help me see it?

Deeper

When have I been a better friend than I realised?

Then ask: And when did I miss something I should have caught?

Deeper

What do you think friends owe each other that acquaintances don't?

Then ask: Have we ever disagreed about that without saying so?

Deeper

Which friendship that ended do you still think about?

Then ask: Was the ending a decision or a drift?

Deeper

What would you want me to tell you, even if it was hard to hear?

Then ask: How would you want me to say it?

Deeper

What's a risk you're glad you took, and one you're glad you didn't?

Then ask: Did you know at the time which was which?

Deeper

How has what you need from friends changed in the last five years?

Then ask: Do the people around you know?

Deepest

If one of us moved across the world, what would you most want us to keep?

Then ask: What could we start doing now so that it lasts?

Deepest

Is there something you've held back from me because you weren't sure how I'd react?

Then ask: Would you rather talk about it now, later, or not at all?

Deepest

When did you feel most alone, and did anyone notice?

Then ask: Looking back, what would have helped?

Deepest

What do you think I'm avoiding?

Then ask: What makes you think so?

Deepest

If we drifted apart, which version of you would you want me to remember?

Then ask: Which version do you worry I'd remember instead?

Deepest

What would you say to me if you knew this was our last long conversation?

Then ask: Is there a reason not to say some of it now?

Light

Which moment from our early days would you most like to relive?

Then ask: What do you think made it feel so easy?

Light

What's one small thing I do that makes your day better?

Then ask: Have you ever told me before?

Light

Where would you take us for a day if time and money were no object?

Then ask: Which part of that day could we manage this month?

Light

What did you notice about me before we got together?

Then ask: Is it still true?

Light

Which of our routines would you defend to the end?

Then ask: And which one could quietly go?

Light

What would you like us to learn together?

Then ask: What has stopped us so far?

Light

Which tradition from your family would you keep for us, and which would you drop?

Then ask: What makes the difference between the two?

Deeper

When do you feel most loved by me, and is it when I'd expect?

Then ask: When do you feel least noticed?

Deeper

What have you changed your mind about since we've been together?

Then ask: Did I have anything to do with it?

Deeper

What would a fair split of the boring jobs look like to you?

Then ask: Where do you think we're furthest from it?

Deeper

How can you tell I'm upset before I say anything?

Then ask: What do you usually do with that?

Deeper

Which of your hopes do you think I underestimate?

Then ask: What would real support look like, specifically?

Deeper

How do you want us to disagree?

Then ask: What does either of us do that makes an argument worse?

Deeper

Which of your needs is hardest to ask me for?

Then ask: Is the hard part the asking, or the answer you expect?

Deepest

What do you think we'll find hardest ten years from now?

Then ask: Is there anything we could do about it now?

Deepest

If you stopped being happy and didn't know why, what would you want me to do?

Then ask: How would I know it was happening?

Deepest

Is there a version of you that you think I'd love less?

Then ask: Where did that worry come from?

Deepest

What does commitment mean to you on a day when you don't feel it?

Then ask: Has that happened, and what did you do?

Deepest

What from your past still shapes how you love me?

Then ask: Is it something you want to keep carrying?

Deepest

If we could keep only one thing about how we are together, what should it be?

Then ask: What would it take to protect it?

Light

What was the house you grew up in like, room by room?

Then ask: Which room do you remember best, and why that one?

Light

What did you want to be when you were ten?

Then ask: What happened to that plan?

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Which family story gets told most often, and is it true?

Then ask: Who tells it differently?

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Which meal tastes like home to you?

Then ask: Who made it, and do you know how?

Light

What did your parents do for fun when you were young?

Then ask: Did they ever have time for it?

Light

What's the best present you ever received as a child?

Then ask: Was it the thing itself, or who gave it?

Light

Which relative were you most like as a child?

Then ask: Are you still?

Deeper

What did your parents get right that you only appreciated later?

Then ask: Have you ever told them?

Deeper

Which rule from your childhood have you kept, and which have you broken on purpose?

Then ask: Why those two?

Deeper

What do you wish you had asked your grandparents?

Then ask: Is anyone still alive who could answer some of it?

Deeper

How was money talked about, or not talked about, when you were growing up?

Then ask: How does that shape what you do with money now?

Deeper

What is our family good at that other families aren't?

Then ask: And what do we avoid?

Deeper

When did you first see your parent as a person rather than a parent?

Then ask: What did you see?

Deeper

Which family role were you given, and did it fit?

Then ask: Have you outgrown it?

Deepest

What would you like to understand about our family while there's still someone to ask?

Then ask: Who would know?

Deepest

What did you have to forgive in your own upbringing?

Then ask: Was forgiving it the same as accepting it?

Deepest

What do you hope this family carries on after you're gone?

Then ask: What would you rather we let go of?

Deepest

Which of your decisions do you think the family still misunderstands?

Then ask: What would you want them to know?

Deepest

What did you give up for this family that nobody thanked you for?

Then ask: Would you make the same choice again?

Deepest

What do you most want to be remembered for by the people closest to you?

Then ask: Is it what they would say now?

Light

What did I spend most of my attention on this week?

Then ask: Would I choose that again?

Light

What gives me energy that I rarely make time for?

Then ask: What would one hour of it a week look like?

Light

Which compliment do I always brush off?

Then ask: What would it mean to accept it?

Light

Which small promise to myself do I keep breaking?

Then ask: Is it the wrong promise?

Light

When was I last completely absorbed in something?

Then ask: What conditions made it possible?

Light

What am I putting off, and what is the delay protecting me from?

Then ask: What is the smallest first step?

Light

Which of my habits would I be glad to see in a friend?

Then ask: And which would worry me?

Deeper

What would I do differently if no one I know could see my choices?

Then ask: Whose approval am I actually working for?

Deeper

Which part of my identity would I defend first?

Then ask: Did I choose it, or inherit it?

Deeper

What do I believe that I have never actually tested?

Then ask: What would a fair test look like?

Deeper

Where does my sense of 'enough' come from?

Then ask: Has the line moved, and who moved it?

Deeper

Which of the stories I tell about my past might be unfair to me?

Then ask: Who else is in that story, and is it fair to them?

Deeper

Which value do I mention most, and when did I last act on it at a cost?

Then ask: What did it cost?

Deeper

What am I tolerating that I would tell anyone else to change?

Then ask: Why does my own case look different?

Deepest

What would I regret not trying if I had five years left?

Then ask: What is one step I could take this month?

Deepest

Who am I when nobody needs anything from me?

Then ask: When did I last find out?

Deepest

What am I still trying to prove, and to whom?

Then ask: What would happen if I stopped?

Deepest

Which of my fears is about failing, and which is about succeeding?

Then ask: Which one is louder?

Deepest

What would I keep if I lost everything else?

Then ask: Does it get the attention that ranking deserves?

Deepest

If my younger self could see my life now, what would surprise them most?

Then ask: Would they be relieved or disappointed, and would they be right?