50 Questions to Ask Your Parents Before It’s Too Late
We always think we have more time…
We assume that one day, when life slows down, we’ll finally sit down with our mom or dad and ask them about their lives. We’ll ask about their childhood, their first loves, and the lessons they learned the hard way.
But life rarely slows down. And often, by the time we’re ready to ask, the memories have started to fade.
The hardest part of recording your family history isn’t the technology, but knowing exactly what to ask. We don’t want it to be too broad or overwhelming. But we also don’t want stuff that’s too specific only to yield a couple of word responses. To get the best stories, you need to ask specific, open-ended questions that trigger memories.
Here is a curated list of 50 questions to spark those conversations, organized by the chapters of their life.
Part 1: The Early Years (Childhood)
The best way to start is with low-stakes, nostalgic questions. These act as "warm-ups" to get the memories flowing.
What was a hobby you had as a kid?
Besides your parents and siblings, which relative do you remember most fondly from your childhood?
What stories have you heard about where your family comes from?
Did you ever get into big trouble at school? What happened?
What was your favorite memory of one of your own parents?
What was the best meal your mother (or father) ever cooked?
Did you have a nickname growing up? How did you get it?
What did you want to be when you grew up?
What was your favorite family tradition during the holidays?
What is the biggest difference between growing up then vs. now?
Part 2: The Teenage Rebellion (Adolescence)
This is often the era parents hide from their kids. Digging here often reveals the most surprising and human stories.
What was the first thing you bought with your own money?
Was there a subject in school that you just couldn't stand?
Did you ever sneak out of the house?
What was your first car? How much did it cost?
Who was the teacher that had the biggest impact on you?
What was your favorite hangout spot in high school?
What was your first job, how was it?
What was the worst haircut or fashion choice you ever made?
What was your original plan after high school?
If you could go back and talk to your 16-year-old self, what would you say?
Part 3: Stepping Into the World (Early Adulthood)
The transition from "kid" to "adult" is full of struggle, humor, and growth.
What was it like moving out of your parents' house for the first time?
What was the hardest job you ever had?
How did you spend your weekends when you were in your 20s?
What was the first big purchase you made as an adult?
Tell me about a time you failed at something. How did you handle it?
Did you ever travel anywhere that changed your perspective on the world?
Who were your roommates, and do you have any crazy stories about them?
What is the biggest risk you took in your career?
How did you handle money when you were starting out? Were you a saver or a spender?
What was the moment you finally felt like a "real" adult?
Part 4: Love and Partnership
Whether they are still married, divorced, or single, everyone has a history with love.
How did you meet [Mom/Dad/Partner]? What was your first impression?
What was your first date like?
When did you know they were "the one"?
What is the story behind your proposal?
What is the hardest part about being married/in a partnership for so long?
What is your secret to resolving an argument?
What was your wedding day like? Did anything go wrong?
Who was your first heartbreak?
What advice would you give to someone about to get married?
What is your favorite memory with your partner before you had kids?
Part 5: Wisdom and Legacy
These are the "heavy hitters." Save these for when you are already deep in conversation.
What is the accomplishment you are most proud of?
What is one thing you regret not doing?
What was the happiest year of your life so far?
What is the hardest decision you ever had to make?
How has your definition of "success" changed over the years?
What is one thing you want your grandchildren to know about you?
What are you most grateful for today?
Is there anything you have always wanted to tell me but never found the right time?
What do you want your legacy to be?
If you could live one day of your life over again, which day would it be?
Don't Ask These All at Once
Looking at this list can feel overwhelming. If you sit your dad down and ask him 50 questions in a row, it won't feel like a conversation, and more like an interrogation.
The best way to capture these stories is slowly.
That is why we built the Tell Me Your Story app. Instead of a massive list, our app sends one thoughtful prompt a week to your parent's phone. They can answer in their own time, recording their voice or writing it down, and the stories are automatically saved for you to keep forever.
It turns a daunting project into a weekly ritual.
Start capturing their story today. Download on App Store | Google Play
