There are so many questions that have come to me after my parents and their generation have crossed over, especially questions about their parents and grandparents. I wish I’d thought of those questions when I had the opportunity to ask.
Now during the holiday season, you might have a chance to ask some of these of your family. Take advantage. I wish I had!!
Here are the four types of questions I wish I’d asked the older generations of our family:
Questions about the jobs and daily life of various family members
Though I did ask my father questions about his job as a machinist, and I feel I know a good bit about my mother’s life as a homemaker (and her job as a home demonstration agent before I was born), I didn’t ask many questions about the jobs of my uncles or what it was like for my aunts as homemakers.
I especially wonder about my grandparents and great-grandparents. We had lots of farmers in our family (typical for agricultural areas of the South in the early 1900s and late 1800s). I sure didn’t ask enough questions about my grandfathers’ work. One was a farmer and the other owned a general store before he lost it during the Depression and went on to other work. I know little about that other work. And I know little about what an average day was like for my grandfathers and grandmothers. Who did what? What time did the day start? How did it end? What did they enjoy? So many questions about their lives come to me now.
I also wonder how they bought their land and houses. What was inherited? What was bought? And when? How did they get the money to buy a house and/or land? What was their first car? Where did they get their furniture? If I had it to do over, I’d ask lots of questions and keep a timeline. That would help a lot with my research on Ancestry.

Questions about dating and marriages
I did ask my parents about how they met, and I asked a little about their wedding, but I wish I’d asked more about the wedding day and paid closer attention to what they told about their honeymoon trip to Washington, D.C. And I wish I’d asked about each one of my aunts and uncles, how they got engaged, what the wedding was like, what did they wear, how long had they known each other, did they go on a honeymoon—questions like that. I wish I’d asked my grandparents the same questions and what they knew about their parents’ engagements and weddings.
I have somewhat of an excuse for not asking my grandparents most of these questions because they had all died before I was 20. But I could have asked more questions of my aunts and uncles.

Questions about the health of various family members
I also wish I’d asked more specific health questions about the generations before me. I vaguely remember stories about a great aunt who had cancer, but I don’t know what kind. I know that heart problems ran through both sides of my family, but I didn’t pay close attention when I was a child and young adult to the health discussions my parents had about their parents.
I wish I’d asked more about the early deaths in our family, questions beyond the mythology that came up around their deaths—you know, the story that was told and retold but was only the framework for what was an emotionally (and perhaps financially) crushing time for all affected.
I especially wish I’d paid more attention to the stories of my great-grandparents, because I think families have patterns that run through generations. Sometimes all it takes is awareness to break a pattern. But if I don’t know what the pattern is, how can I break it? Sometimes it’s a physical health challenge, but sometimes it may be a mental health challenge. Because my family considered mental health challenges shameful, it was harder to get information in that area.
And that leads me to my last category:
Questions about the family secrets
The family secrets may be the most important, because that’s what hasn’t been acknowledged and dealt with. And those questions are the hardest to ask.
Sometimes people will share those secrets as they get closer to the end of their lives. I know some of my relatives shared more as they aged. But most did not.
I firmly believe that those secrets hurt families as much as health issues—and probably contribute to health issues.
This is the category that I know (and knew) least how to approach. I didn’t want to be prying, to make people uncomfortable.
Maybe the best way to find family secrets is from community members not in the family.
With so many people getting DNA testing to find their ancestry, many family secrets are going to be revealed. I love watching Long Lost Family and seeing family members find each other after decades of separation. Some have even been unaware that they had these family members.
I did DNA testing through Ancestry, and a family member who had been a secret did indeed contact me. I expect that will happen many thousands of times in families around the globe as more and more people have DNA testing.
“What can you do to promote world peace? Go home and love your family.” – Mother Teresa
If you choose to ask some of these questions of your family, do that with no judgment and lots of love. And don’t push. Sometimes questions that seem innocuous are loaded in ways we don’t understand. Yet.
I’m grateful to each one of my family members who made it possible for me to have such a textured and supported life. They each have contributed to it.
And my questions are my way of honoring them as individuals who survived and thrived through lifetimes of challenges.
I want to honor each one of them as people who helped make me who I am today. Because each generation has made a valuable contribution.
I admire your questioning – I met some relatives a few years ago – Far from home but oh so close after meting and talking with them – BTW i also feel sad around my birthday xx
So many things I didn’t think to ask! I haven’t searched my ancestry back as far as Europe yet, but my DNA test says I’m about 2/3 from Britain, and there’s overlap with Ireland. Ireland sure felt like home when I was there 20 years ago.