“When was your first kiss?” & other fun questions to ask Mom and Dad
The days are passed when you might cringe with embarrassment imagining your parents’ first kiss (at least, I hope they have!). But have you ever asked them about it?
How about their most embarrassing moments? The time they were really and truly naughty? The lie they told you when you were a kid?
One of the consistent reactions I get when life story books are presented to families is this: “I never knew this side of my mom” or “I always thought of Dad simply as Dad—how wonderful to discover him as a person!”
So many questions I ask my personal history clients revolve around transitional times in their lives: decisions that impacted the course of their life, and lessons learned on the path to becoming who they are now. But life isn’t just about the milestones; it’s about the everyday moments and experiences that add up to a life.
And you know what? A lot of those moments are funny—and fun. Why not explore them in conversation with your parents? You’ll enjoy yourselves even while you get to know them on a whole new level! (Bonus points: Hit “record” on your smart phone or a digital recorder to ensure their stories are captured for posterity.)
38 questions to explore your parents’ fun sides
Don’t just ask this questions that appeal to you: Invite stories. Ask follow-up questions. Listen with interest, and no doubt questions even better than the ones below will come to mind as your parents are sharing. Most of all—have fun!
Questions to Get You—and Your Parents—Smiling
What is the funniest fashion fad you gave into during your teen years? In your twenties?
Tell me about a time you laughed inappropriately.
What is the funniest thing you recall Grandma/Grandpa ever doing?
What are some funny things your kids said or did when they were little?
When was your first kiss? Tell me the story.
What’s the most embarrassing thing that has ever happened to you?
What are you hoping I don’t ask? Come on…
Tell me about a time you were unabashedly naughty.
What’s the most satisfying thing you ever got away with?
Did you ever tell us kids white lies when we were young?
What is the funniest practical joke you ever played on someone?
Do you remember a favorite lullaby or bedtime story from your childhood?
Tell me about any pets you have had—and maybe a time or two they made you truly happy.
Do you have any goofy tendencies or unique habits?
If someone gifted you $5 as a kid, what would you immediately want to buy?
Seemingly Benign Questions that May Yield Surprisingly Deep Answers
What is the worst date you were ever on?
How would you describe your sense of humor?
What has been your grandest adventure?
What always makes you laugh?
What is the most incredible dream you have ever had?
Who from your childhood would you characterize as reliably funny?
What is the nicest thing you have ever done for someone?
What is the nicest thing anyone has ever done for you?
What is the biggest surprise you have ever gotten?
Questions their Spouse May Prefer to Answer on their Behalf
Tell me a funny story about a time Mom/Dad got a little tipsy.
Have you ever had to rescue Mom/Dad from an embarrassing guffaw?
What did you do for fun on your dates together (allow both to reply—often the interplay of their reminiscing together will be as fun as their answers!)
What scenes would be on your spouse’s blooper reel?
Quickfire Round: Questions that Reveal Fun Details
Did you have nickname(s) as a child?
Can you remember any knock-knock jokes or funny riddles?
What was your favorite cartoon character as a child?
What is your favorite… card game?
… ice cream flavor?
… musical group?
… movie?
… place to visit?
… candy bar?
Make a goofy face, won’t you? (Get your camera ready!)
Get your free guide of Essential Family History questions
All the questions (not just the funny ones!) to ask your parents to capture their stories, presented in a beautiful printable guide
I'’d be honored to hear your stories.
Do you prefer to have a professional personal historian conduct interviews with you or your loved ones? That’s what I’m here for! Schedule a free 30-minute consultation to see how we can work together—I can’t wait to hear all about you!