Posted by Frank
https://postsecret.com/2025/06/15/25-questions/
http://postsecret.com/?p=23348
I asked PostSecret followers on facebook for once-in-a-lifetime questions to ask my dad for an unforgettable interview. Over 700 replies with more than 1,000 questions came back.
This was the original post:

I was thrilled with all the thoughtful questions shared with me, from the delightful to the profound. I read them all and picked 25 to ask my father. At a family dinner the night before our day of tandem paragliding, as an experiment, I peppered three into our conversation. . . it didn’t go well.
Like many families, ours was far from perfect, with divorce and estrangement being a part of it. So when other family members began responding to some of my father’s answers, long-buried feelings and some judgement turned the interview sour. Because of that learning experience, I changed some of my questions and gained three insights for when I would try again the next day.
• Avoid questions about regrets or mistakes. Instead, start with questions that include the word “favorite”, like, “What’s your favorite decade and why”?
• Try to keep the questions open-ended and let responses spark other questions naturally. Aim for a flowing conversation rather than an interview.
• Really listen. . . No, really listen.
On the two hour drive to the Gliderport the next day, it was just my father and me in the car. I told him how much it meant to me to go through these questions and get to know him better. He was game so I cautiously started. He passed on some of the questions, but then really began to share a lot with me, including a secret. He even started asking me some of the same questions! The spirit in the car was supportive and generous, with some heartfelt laughs as we used questions as prompts for our once-in-a-lifetime conversation.
Even though we were unable to do any gliding because of wind conditions, I’ll never forget that day and the new appreciation I discovered for my father. I can’t reveal the secret he told me but another part of our conversation shocked me. I asked this gentle and caring man; “What is the most common misconception people have about you?” He said. “When I was ten-years-old, my mom spanked me for the last time. I don’t think you know how stubborn I was then but you do know how stern your Grandmother could be. I remember through my tears and pain looking at my mother and saying, with spite, ‘I like getting spanked’!”
Here are the 25 questions that guided our conversation.
~~~
Do you have a favorite snack, song, television show, recipe, comedy?
Can you tell me about your best friend when you were a kid and one of your adventures?
Can you describe a favorite memory about a family member?
What is the oldest story you know about our ancestors?
Is there something about me that you have always wanted to know but have never asked?
If this was to be our very last conversation, is there anything you would want to say to me?
What is your first memory?
Did you ever get into trouble as a kid? What happened?
If there was a biography of you, how would you want to be described?
What choice are you thankful that you did not make?
What is the best advice you remember from your father?
Is there anything you wish you had said to someone but didn’t have the chance?
Can you teach me something?
What is something you would like me to ask you?”
What do you wish you would have spent less time worrying about?
What is something you deliberately did not tell me as a child and why?
What is the best part of your day? What makes you feel most alive?
What is the last thing you changed your mind about?
What things helped you get through a difficult time in your life?
Over the course of your life what trip or place was most special? Why?
What would you like to re-experience again because you did not appreciate it enough the first time?
Can you tell me something about yourself that I don’t know that you think would surprise, shock or delight me?
What habits served you the most through life?
What is the best mistake you have made, and why?
What do you hope my siblings and I have learned from you?
How are you doing right now? Is there anything on your mind right now that you’d like to talk about?
~~~
(When my father visits again, I’ll be sure to have his favorite comedy and snack ready.)
~~~
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https://postsecret.com/2025/06/15/25-questions/
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