Don't Regret That You Never Asked Them

A loved one recently died, or was otherwise permanently lost to you. You are in mourning. Later, you begin to process what you have lost. In addition to other emotions, you feel regret. “There were so many things I wished I had asked about.”

What were the questions?

Perhaps you wanted to know more about your mother’s childhood. What was she like as a little girl? What did she fear? What did she dream about becoming? Who was her first love? What did she regret? What were the happiest moments of her life?

Perhaps it was your father. You realize that although you knew him as your father, there was an entire person you never completely knew. What did he believe before you were born? What experiences changed him? What did he think about his own father? What did he consider his greatest accomplishment? What did he wish he had done differently?

Or perhaps you wanted to ask a spouse, brother, sister, friend, or grandparent questions that seemed unimportant at the time but suddenly seem enormously important now.

The problem is that death changes the nature of a question. Before death, almost any question can be postponed. There will be another visit. Another telephone call. Another holiday. Another opportunity. After death, there isn't. That is one of the cruelest features of bereavement. The person who possessed the answers is gone, but the questions remain.

Research suggests that this experience is not unusual. A study of bereaved people found that they commonly wished they had discussed subjects involving personal information, their relationship, death and dying, and practical matters that would follow death. People often avoided these conversations because they wanted to protect themselves or the dying person emotionally, because of differences within the relationship, or because the person's condition made the conversations difficult.

In another study involving bereaved families of cancer patients, approximately one-third said they regretted not having talked sufficiently about death. Interestingly, a much smaller percentage regretted having talked about death. That finding deserves attention.

We often avoid talking about death because we believe the conversation will make death more frightening. Sometimes it does make the moment uncomfortable. But discomfort is temporary. Lost opportunity is permanent.

There is a difference between causing discomfort and causing harm. A difficult conversation may produce anxiety, tears, silence, or even disagreement. But avoiding the conversation can leave the survivor with questions that can never be answered.  This does not mean that every possible question should be asked. Nor does it mean that we should interrogate someone we love simply because death might someday occur. Conversations are relationships, not interviews.

The point is something more fundamental: we tend to assume that we know the people we love better than we actually do. We know the roles they played in our lives. We know the stories they told repeatedly. We know their habits, their opinions, their personalities. But knowing someone is not the same as knowing that person's history. There may be an enormous amount of information hidden behind the person we see every day. And sometimes we don't discover how much we didn't know until it is too late.

Regret is usually treated as a negative emotion. We think of it as something we should overcome. But recent research on bereavement-related regret suggests that regret can also function as an invitation to examine what mattered to us in the relationship. One recent qualitative study described bereavement regret as an active and continuing experience that connects the present self with the past self and can draw attention to one's values.

In other words, regret may contain information. When I say, “I wish I had asked my father about his childhood,” I am not merely expressing sadness. I am revealing something about myself. I wanted to know him. That realization may be painful, but it is also valuable.

Perhaps I can no longer ask my father. But I can ask someone else. I can ask my mother. I can ask my brother. I can ask an older friend. I can ask my children about their lives while I am still here to hear the answers. And perhaps I can tell them the things I have assumed they already know.

There is another important reason to ask questions while we can. Questions do not merely obtain information. They communicate interest. When you ask someone, “What was your childhood really like?” you are saying, in effect, “Your life matters to me.” When you ask, “What are you most proud of?” you are saying, “I want to understand what has been important to you.” When you ask, “Is there anything you wish you had done differently?” you are giving that person permission to reflect rather than merely remembering. And when you ask, “Is there anything you want me to know that I have never asked you?” you may open a door neither of you knew was there.

We frequently wait for the perfect opportunity to have these conversations. There probably isn't one. The person may be busy. You may be busy. The television may be on. Dinner may be waiting. Someone may say, “That's a strange question.” Ask anyway. You don't need to announce that you are about to have an important conversation about mortality. In fact, ordinary conversations may be better. A question can be asked while sitting at the kitchen table. While driving. While walking. While looking through old photographs. While having a cup of coffee.

The conversation doesn't have to be solemn. It can be funny. It can wander. It can become something completely different from what you expected. That may be its greatest value. We tend to think that what we want from these conversations is information. But perhaps what we really want is connection.

The emerging understanding of grief supports this idea. Contemporary approaches to bereavement recognize that continuing a symbolic or emotional relationship with someone who has died can be a normal part of mourning. The goal is not necessarily to erase the relationship but to integrate it into the survivor's continuing life. That means the questions we failed to ask don't necessarily have to become meaningless. We can search photographs. We can talk with relatives and friends. We can read old letters. We can visit places where the person lived. We can reconstruct stories from fragments.

Sometimes we can simply acknowledge the unanswered question. “I wish I had asked.” There is no requirement that every regret be solved. Some questions will remain unanswered forever. That is part of being human. But there is a lesson available in the regret.

If someone you love is still alive, ask. Ask about the things you think you already know. Ask about the things you think you don't need to know. Ask about childhood. Ask about love. Ask about failure. Ask about success. Ask what they fear. Ask what they believe. Ask what they regret. Ask what they hope. Ask what they remember about you.

Perhaps most importantly, ask: “What is something about you that you wish I knew?” Then be quiet. Let them answer. Because someday, you may desperately wish you had asked. And someday, someone may desperately wish you had asked you.

 

References

McCusker, P.J. (2023).  Questioning & Answering: How, Who, When, & Where.   Amazon.

Generous, M. A., & Keeley, M. (2017). Wished for and avoided conversations with terminally ill individuals during final conversations. Death Studies, 41(3), 162–172. https://doi.org/10.1080/07481187.2016.1236850.

Miyashita, M., et al. (2017). Talking about death with terminally ill cancer patients: What contributes to the regret of bereaved family members? Journal of Pain and Symptom Management. https://doi.org/10.1016/j.jpainsymman.2017.07.010.

Wright, K. B., et al. (2023). Survivors' perspectives on saying goodbye: Implications for end-of-life engagement across the lifespan and grieving process. Death Studies.

APA Dictionary of Psychology. (2018). Continuing bond. American Psychological Association.

Recent qualitative research on bereavement-related regret: “I could have”: The lived experience of bereavement-related regret. Death Studies (2025). https://doi.org/10.1080/07481187.2025.2502987.

Desiring, Acquiring, Keeping, and Discarding

You don't hear the 1980s meme "Whoever dies with the most toys wins" much anymore, but the acquisition mindset is as strong as ever. Just look at how many packages show up on doorsteps each week. So it's worth asking an uncomfortable question: why do we want all this stuff in the first place?

We tell ourselves we buy things because we need them. Sometimes that's true. But often "need" quietly slides into "want," then "I deserve this," then "I won't be satisfied until I have it."

There's a psychological arc here. Desiring something is pleasurable even before we own it — we imagine how the new car will feel, how much easier life will be with that appliance. The object becomes a small promise about the future. Then we acquire it, feel a brief surge of satisfaction, and eventually it just becomes part of the background. What was new becomes normal.

This is why chasing possessions can feel like running on a treadmill. Research on materialism consistently links placing high value on possessions with lower well-being — though the picture is nuanced; motives, circumstances, and having enough resources all matter. Still, making acquisition a central measure of a successful life isn't a reliable path to happiness.

A Sampling Period for Stuff

David Epstein's Range argues against specializing too early. He describes a "sampling period" where people try different things before committing to one path. What if we applied that to possessions?

Instead of deciding we need to own something, we could experiment with the activity first. Rent or borrow the bike before buying an expensive one. Cook with what you have before filling the kitchen with gadgets. Ask whether you actually live the lifestyle you're buying for. Explore before you acquire.

That runs against consumer culture, which pushes us to buy first and discover later. Epstein also borrows a distinction from psychologist Robin Hogarth: "kind" learning environments have stable patterns and fast, accurate feedback; "wicked" ones don't. Our relationship with possessions is a wicked environment — we're bad at predicting what will make us happy, how long we'll enjoy something, or whether it'll solve the problem we thought it would. Our preferences, bodies, and lives keep changing, yet we treat purchases like permanent solutions to temporary problems.

The Weight of Keeping

Keeping isn't just the opposite of discarding — it often requires justification. I might need it someday. It was expensive. It reminds me of someone. Sometimes these are good reasons. Sometimes they're just stories that make letting go feel harder than acquiring.  There are circumstances, however, when keeping is primarily due to lack of attention to and blissful ignorance of the price we pay for keeping our possessions

The physical cost is obvious: stuff takes space, time, and maintenance. The mental cost is subtler — every possession is a small unfinished decision (use it? fix it? sell it? feel guilty about it?). One object is nothing; thousands create an environment of unfinished business.

There's an interpersonal cost too. Possessions live in shared spaces, and one person's keepsake is another's clutter. Arguments about "stuff" are often really about control, identity, money, or whose priorities get to dominate the household. Constant acquiring consumes shared space and shared patience, not just money.

Experiences vs. Things — With a Caveat

Research comparing material and experiential purchases generally finds people get more well-being from experiences, partly because experiences create social connection and become part of our life story. But the advantage depends on circumstances — for people with fewer resources, a possession that solves a real problem can be just as satisfying as an experience.

None of this is an argument for anti-materialism. A good chair, a reliable car, a well-equipped kitchen — these genuinely improve life. The question isn't whether possessions are good or bad, but whether they're serving our lives or whether our lives have become organized around acquiring, maintaining, and protecting them.

Letting Go

Discarding is hard because it forces us to admit our past selves made choices our present selves no longer endorse — the shirt for a life never lived, the exercise equipment for a resolution that faded, the "someday" books. Letting go means saying, "I thought this would matter to me. It didn't. That's okay."

This connects back to Epstein: his case for range isn't "try everything forever" — it's sample, learn, find what fits, and be willing to change course. Our possessions deserve the same treatment. We can acquire without assuming permanent obligation, keep what still serves us, and discard the rest without treating it as failure.

Keeping Score Differently

The goal isn't owning as little as possible — that's just obsession in a different direction. The goal is owning consciously, so our homes reflect our lives rather than the accumulated evidence of every impulse we've had.

As the old line goes — sometimes attributed to Marcus Aurelius or Seneca — "everything you own owns you." Maybe the real lesson isn't "he who dies with the most toys wins." It's closer to this: he who knows what is enough has already won.

                                                                            References

Epstein, David. Range: Why Generalists Triumph in a Specialized World. Riverhead Books, 2019. 

Pandelaere, Mario. "Materialism and Well-Being: The Role of Consumption." Current Opinion in Psychology, 2016. 

Van Boven, Leaf. "Experientialism, Materialism, and the Pursuit of Happiness." Review of General Psychology, 2005. 

Guevarra, Darwin A., and Ryan T. Howell. "To Have in Order to Do: Exploring the Effects of Consuming Experiential Products on Well-Being." Journal of Consumer Psychology, 2015.

Lee, Jacob C., Deborah L. Hall, and Wendy Wood . "Experiential or Material Purchases? Social Class Determines Purchase Happiness." Psychological Science, 2018.

Epstein, David. "Kind and Wicked Learning Environments." Range Widely, May 16, 2024.

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