Losing someone you love brings with it a kind of wistful mystery: who was my loved one … really? What do I wish I knew about them that I didn’t even think to ask them while I could? What would I give up chocolate for the rest of my life to know? (Granted, that would have to be a really, really important question.)

I now know things about people who have been important to me that I didn’t know while they were alive — about a mental illness, for example, or a key relationship they had had. Had I sat with them and asked meaningful questions, I would have opened up a really important part of their lives and we would have had that intimacy between us.

Your knowing the pang of that eternal wondering can be a spur to your thinking ahead about the mystery inhabiting the people you love who are still here. It’s probably a good thing that that mystery is never going to be entirely penetrable — would you really want it to be? — but there are things you know you wonder now, and now is the time for you to find your moment, and the right way, to pop your question. 

What keeps us from asking real questions of those we love?

If you haven’t already popped your question, you may have a “good” reason.

Maybe …

You’re afraid of the answer you might get. (It can’t be worse than the answer that’s lurking around in your head.) 

You feel as though you don’t know how or when, or whether it’s even okay, to pose the question. (You can warm up to it; you don’t have to ask in one perfectly worded way.) 

You’re afraid of saying the wrong thing as you ask. (If it’s that awkward to ask, your family member will see you floundering and will become unusually patient. 😉 )

The intimacy of the question feels a bit much. (So take it in stages.)

You feel as though you’re in too much pain yourself. (Focusing outside yourself is actually going to help.) 

The question is a gift to the person you love.

Your mother-in-law longs to be known. Your irascible cousin is actually just as tender inside as you are. Your buddy has no one else to tell. 

The question you form in your heart, the one that will help you understand how they experience or have experienced the world, is the one they long to hear. And it’s the one you’ll be glad you asked while you’re both still around.

Truly, just about everyone loves to talk about themselves. And once you let them know it’s okay for them to take up space, you’ll learn a lot more than you thought you would. 

I’ll tell you a story.

When my mother’s breast cancer returned, already advanced by the time it was detected, she, my father, and I went shoe-shopping (yes, that’s what we did — let me tell you about a good pair of shoes). At one moment, my father strayed up ahead, perhaps seeing something in another shop window. 

As my mother and I walked more slowly behind, I thought of something I knew I’d wonder about her, a woman about whom people first would remember how well she was always “put together.”

Early in feminism’s second wave, my mother invented a job for herself, one that had started on a volunteer basis but eventually led her to earn more than my father did as a faculty member. She wore snazzy tailored outfits to work. 

I wanted to know how she related to her own appearance – not from a position of vanity, but for the advantages it may have given her in life or how it had shaped her worldview. She had banked so much on that. 

So I popped the question, “Mom, how do you think your life might have been different if you hadn’t been born pretty?”

She stopped in her tracks, turned her gaze on me, and spoke uncharacteristically sharply. “Who says I’m pretty?” We had never discussed this directly before, I’d just assumed it. 

After she died a few months later, thinking of her as having overcome a sense of not being pretty, rather than simply banking directly on her confidence in it, has given me an entirely different way of understanding my mother’s drive.

I’m so glad I asked. 

A good question can make a complex answer easy. 

It can be asked at such a time, and in such a way, that there’s room for the person to think through their answer. (You’re leaving about 10 times more space for them to answer than you’re ordinarily comfortable with.)

The answer is something that, with just a little bit of stretch, they would want to tell you.

You’re framing the question that you’ve already done some a bit of the thinking for them but are leaving room for their own self-definition and self-discovery. 

It all comes, I believe, down to a single über-question: 

What is it like to be you? 

Make your question about their experience. 

About how they have perceived a hard decision or moment in their lives —not just what happened, but how and why it happened. 

And remember, above all, to ask your question in such a way that “yes” or “no” cannot be the answer to it. 

What does it take to be a good popper of questions? 

Imagination, Empathy, and Humility — not necessarily in that order. 

The best journalists and interviewers know how to pose questions that reveal the soul, the story underneath the story that is first told. 

They start with imagination. They believe there’s something there to be discovered and they believe that because they’ve imagined the possibilities. 

Interviewers on long-form programs or for feature stories in print pose their questions in a fundamental spirit of appreciating the other’s humanness. They ask their questions in such a way that, whatever the answer might be, it will be understood. They ask questions in ways that avoid objectifying. Rather than “How could you have made such a decision?” they ask, “What was going on inside you as you made your decision to …?” That’s empathy. 

And they appreciate that they do not know the answer, that that answer is the other person’s own to share (or not to), and that, indeed, if they can only pay quiet attention, the other person may teach them the very question they should have asked. That’s humility.

The most important part of daring to pop: your self-preparation

Formulating your question.

Trying to see and hear your question from the other person’s perspective.

And, above all, quieting yourself. Emptying yourself of your preference for one answer or another, or for putting too quickly their answer into a box of your own crafting. 

And then seizing the moment.