25 Questions I Wish I'd Asked My Mother — Written From the Other Side of Six Weeks

My mother was diagnosed with pancreatic cancer on a Tuesday in April. She died six weeks later, on a Thursday in early June, in the guest room of my sister's house, with the window open because she'd asked for the window open.

I want to tell you what happened in those six weeks, because it's the only way to explain why I'm writing this list the way I'm writing it.

For the first ten days after the diagnosis, we talked mostly about logistics. Hospice arrangements. Which of the grandchildren would come when. Whether she wanted to stay in her apartment or move to my sister's — she chose my sister's. The paperwork. The estate. The car she wouldn't be needing anymore. I want you to understand this so you know I'm not going to pretend the whole six weeks were profound conversations. Most of the first week and a half was ordinary and administrative, and it needed to be.

It was around day twelve, sitting with her one afternoon while she was tired but still lucid, that I realized I was running out of a resource I'd assumed was infinite. My mother had been the person I called for as long as I'd had a phone. I hadn't called her enough — nobody ever does — but she had always been there, and the questions I could ask her had always been available.

She was going to die in a month, and there were things I had never asked her that I had assumed I would always be able to ask.

That afternoon I started keeping a list in a small notebook I bought at the drugstore on the way to my sister's. Not questions to ask her — questions I found myself needing to ask, and realizing I'd never asked. Some of them I did ask her in the weeks that followed. Some of them I asked and got answers that took my breath away. Some of them I never got to. Some of them I only realized I'd needed to ask after she was gone, when it was too late.

The list below is that notebook, cleaned up. I've organized the twenty-five questions into five sections, each addressing a different layer of a life. Read them in order or skip around. But I want you to know two things before you start:

First, you don't need six weeks of hospice to have these conversations. You can ask any of these questions on a Sunday afternoon, during a normal visit, when nobody is dying. The reason I'm writing this from the other side of six weeks is that the shortness of that window taught me what actually mattered. But the questions don't require a deadline to work. They work better without one.

Second, don't try to ask all twenty-five in one sitting. Pick one. Wait for a natural pause in an ordinary conversation, and ask it. Some of them she'll answer briefly and move on. Some will open into an hour you'll remember for the rest of your life. Both are fine.

Section One: Childhood (5 questions)

These are the questions that get the easiest yes. Most people love talking about their childhood, and your mother is no exception. Start here — even if you think you know the answers. You usually don't.

1. What did your bedroom look like when you were nine?

Not "tell me about your childhood." Something specific enough that she has to close her eyes and see it. The bedspread. Where the window was. What was on the walls. What the light was like in the morning. My mother described a small yellow room with a single dormer window and a picture of a horse she'd cut out of a magazine, taped up with what she remembered was medical tape from the family bathroom. I hadn't known she'd loved horses. I hadn't known there had been a picture on the wall. She was seventy-eight when I asked, and she'd never told anyone in our family about that horse.

2. What did your mother smell like?

Sensory memory is stored differently than narrative memory. This question bypasses the polished version of the past and reaches something older. The answer will often be a specific thing — a perfume, a soap, a kitchen. My mother said "flour and lemon peel," and then didn't say anything for a while.

3. Who was your best friend at ten, and what happened to her?

Almost everyone had one. Almost nobody has kept in touch. The story of what happened — where they moved, what they became, why the friendship ended — is often a small, aching microcosm of a whole era of your mother's life. My mother's friend Betty had moved to Ohio at twelve, and my mother had never seen her again. She said the name and looked at the ceiling for a long moment.

4. What is the first time you remember being genuinely afraid?

This one is more intimate than it sounds, but it's also gentle — it's asking her to remember an emotion, not to analyze it. Fear is one of the earliest memories most people can access. My mother's was a house fire she watched from the sidewalk when she was five. She hadn't lived in that house — it was a neighbor's — and no one had been hurt. But she remembered the sound of the fire. She said it sounded like paper.

5. What did you want to be, before you knew you were supposed to be something else?

Every woman of my mother's generation had a first answer to this question that got overwritten by a second answer somewhere in adolescence. My mother said "a marine biologist," which she'd never mentioned in fifty years of being my mother. She'd wanted to study the deep ocean. She'd become an accountant.

Section Two: Decisions (5 questions)

These require a little more trust. Ask them after you've spent an afternoon with the childhood questions and she's warmed up to the shape of the conversation.

6. What was the closest you came to a completely different life?

Everyone has one. A job they almost took, a person they almost married, a city they almost moved to. The question is not whether they regret the choice — it's whether they've ever told anyone about the fork. My mother had almost moved to Alaska at twenty-two, with a man she never named. She stayed because her own mother had gotten sick that summer. I had never heard of any of this.

7. What was the hardest decision you ever made?

Not the biggest, not the most important — the hardest. There's a difference. The biggest decisions are often the easiest, because the stakes make them clear. The hardest ones are usually smaller and stranger and involve competing loyalties. My mother said the hardest was deciding not to take our family to see my grandmother one last time, because the flight would have used up the money we needed for winter heating. She was thirty-one. She thought about it for the rest of her life.

8. Was there a decision you made that you wish someone had talked you out of?

Different from regret. This is asking about the absence — the friend, the parent, the priest, the counselor who might have been there and wasn't. It reveals who your mother was lonely inside her own life at various points. Handle the answer with care.

9. What did you decide about your parents that you now think was wrong?

Every generation forms judgments about the generation before it that soften with age. Asking your mother to name one is asking her to give you a small confession, and it will draw her closer. It may also help you not repeat the same softening about her, thirty years from now, when it's too late.

10. What is one thing you did that you never told your own mother?

Even at seventy-eight, there was something. There always is. My mother told me and then made me promise not to tell my sister. I still haven't.

Section Three: Regrets (5 questions)

The heaviest section. Do not ask these if you sense she doesn't want to go there — read the room. If she's willing, these are where the deepest healing sometimes happens for both of you.

11. Is there anyone you owe an apology to that you never gave?

Sometimes she'll name someone. Sometimes she'll say "I don't want to talk about it" and you'll know there's someone. Both answers count. If she names someone and that person is still alive, you can gently ask whether she'd like your help reaching them. Sometimes she will.

12. Is there anyone who owes YOU an apology that you never got?

Equally important. This one is often easier for her to answer, because it doesn't require her to feel guilty. But listen closely — the story of the apology she never got is often the story of a wound she carried for decades that shaped things you didn't know were shaped.

13. What did you tell yourself would happen eventually, that didn't?

This is a question about the deferred life. Everyone has one — the trip they were going to take when the kids were older, the hobby they were going to pick up when they retired, the person they were going to become. Some come true. Some don't. The list of what didn't is a private inventory most people never share.

14. Was there a time when you weren't yourself for a long stretch?

Depression before it was a word your mother's generation used. Grief that lasted longer than acceptable. A marriage that emptied out. She may deflect. She may not. But asking gives her permission to name something that has never been named.

15. If you could unmake one thing, what would it be?

Only ask this if the conversation has earned it. The answer, if you get one, will change how you understand her life. My mother said something in response to this question that I have never repeated to anyone, and I don't plan to.

Section Four: Love (5 questions)

These are the questions that people remember afterward as the ones that mattered most. Ask them slowly.

16. When did you first know you were loved?

Not by whom. When. The specific moment. For my mother it was her father lifting her onto a horse at a farm when she was four — the same horse she'd have to leave behind later in the year the farm was sold, which was probably why she'd cut the picture from the magazine at nine.

17. What did you learn about love from your parents that turned out to be wrong?

Every family passes down assumptions about love that don't survive contact with the real thing. Asking her to name one is asking her to give you her own hard-won correction — a piece of wisdom she never got to explicitly teach you.

18. What did my father do that made you fall in love with him?

If your father is still alive, ask this in his presence sometimes. If he isn't, ask it when you're alone with her. The answer will be small and specific — not the version she told at anniversaries. The real version is a moment nobody else saw.

19. Was there anyone else you ever loved that we never knew about?

Ask this only if you're ready to hear yes. Most mothers of a certain generation carry at least one story of a person they loved before, or beside, the person they built a life with. Sometimes the story is happy. Sometimes it's sad. It is always more than you expected.

20. What have you loved that had nothing to do with any of us?

Your mother had a self before she became your mother, and she carried it the whole time. This question is asking her to give you a piece of that self. It might be a book. A place. A season of the year. A song. My mother said "the ocean at Cape May in the two weeks after Labor Day." She hadn't been in fifteen years.

Section Five: Wisdom (5 questions)

The final section. Ask these near the end of a visit, or on a walk, or in a quiet car ride. They're the questions your mother will remember being asked.

21. What do you know now that you would tell yourself at twenty-five?

Different from "what advice do you have for me." This is asking her to be tender with her younger self, which is often easier and more honest than being tender with anyone else.

22. What do you think happens after?

Not a demand for a theological answer. An invitation to say what she actually believes, or hopes, or fears, or doesn't know. Most mothers have never been asked this by their children. Most children never think to ask.

23. What have you forgiven yourself for?

The reverse of the regret question, and often more meaningful. What she has managed to forgive herself for is a private accomplishment few people will ever know about. Asking is honoring it.

24. What have you not forgiven yourself for that you'd like to?

Only ask this if the conversation is deep enough to hold it. The answer, if she gives one, is often something you can help her carry the last part of the way.

25. Is there anything you want me to know that I haven't asked?

The last question, and the one I wish I'd asked earlier than day thirty-eight. The answer, when I finally asked my mother, took most of an afternoon. Some of what she said I already knew. Most of it I didn't. All of it I would have missed forever if I hadn't asked.

What I Never Got to Ask Her

I want to name these, because part of the honesty of this article is admitting the list is incomplete.

I never asked her what she was proudest of, and I don't know. I have guesses. I would rather have known.

I never asked her whether she had any regrets about the way she had raised my sister and me. I don't know if she thought she had done a good job. I suspect she did, because she was the kind of woman who would have. But I didn't ask, and she didn't say, and now I never will.

I never asked her what she wanted us to remember about her. She had opinions. She always did. But I didn't ask, and the memorial we planned had to guess, and I've wondered a hundred times since whether we got it right.

These are the three I most wish I had asked. That's why I put question 25 last: it's the question that would have caught all of them if I had asked it sooner.

How to Actually Use This List

Not as a checklist. Not as an interview. Please don't sit your mother down with a printed page and start reading questions from the top.

Here's what I'd do, if I could go back:

Pick one question a month. Ask it on a Sunday, during an ordinary phone call, in the middle of some other conversation. Casual. No warning. "Mom — I was thinking the other day, what did your mother smell like?" Let the answer be whatever length it wants to be.

Write down what she says afterward, not during. Don't take notes in front of her. It changes the shape of the conversation. Write down what you remember later, in your own words. If it matters, you'll remember it.

Ask follow-up questions. The value of these questions is not the first answer — it's the second and third answer that come out when you ask "what do you mean by that?" and "what happened next?" Silence is fine. Let her fill it.

Don't ask them all. Not every question fits every mother. Some of these will land wrong for yours. Skip them. The point is not the list, it's the conversation.

If you'd like a gentler version of this — daily prompts you can use with any older parent, spread over a week — I built a Free 7-Day Family Journal that grew directly out of the notebook I kept during those six weeks. It's not this list. It's simpler and smaller and easier to start with. But it comes from the same place.

A Note If You're Reading This Because You've Already Lost Someone

I know some of you are here because you were googling in the middle of the night, and the "before it's too late" in the title landed the wrong way, because it already is.

I want to say something to you specifically. The questions you didn't ask are not evidence of a failed relationship. Nobody asks enough. Every adult child, at every deathbed, in every era, has left the room wishing they had asked one more thing. It is the shape of the loss, not the shape of the love.

The other thing I want to tell you: many of these questions can still be asked, of other people who knew her. Her siblings, if any are alive. Her oldest friends. The neighbor who lived next door for twenty years. Ask them what she was like at forty. Ask what she said when they were alone. Sometimes the answer will be someone you hadn't quite known — and that person is still real, and still yours, and still available to you.

The dead don't stop teaching us. They just require more of us to learn.