Funny questions to ask your parents
6 questions
Not every question has to be heavy. These ones are warm and a little ridiculous — the funniest thing that ever happened to them, the prank that nearly ended a friendship, the embarrassment that took years to laugh about. Good for a long drive or a slow dinner. Good for breaking the tension if you're working through harder material elsewhere.
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All 168questions, arranged by theme — print it, bring it to Sunday dinner, or keep it by the phone. We'll email it to you free.
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Humor
- 01
What's the funniest thing that's ever happened to you?
Ask if it was funny at the time or only in hindsight.
Have us text this one → - 02
Who in your life has made you laugh the most over the years?
Ask what kind of humor it was — were they a storyteller, a quick wit, just naturally absurd?
Have us text this one → - 03
What's the most embarrassing thing that's ever happened to you?
Ask how long it took before they could laugh about it.
Have us text this one → - 04
What's a story from your life that always gets a laugh at family gatherings?
Ask if it ever gets embellished with each retelling.
Have us text this one → - 05
What's something that always makes you laugh, no matter how often you see it?
Ask where they first encountered it.
Have us text this one → - 06
Have you ever played a really good prank on someone — or had one played on you?
Ask if the relationship survived it.
Have us text this one →
How to actually ask these
- ·Pick three or four. Trying to ask all of them in one sitting will exhaust you both. The best conversations come from one question that opens up into twenty minutes of unrelated stories.
- ·Don't correct or argue. If their memory of an event doesn't match yours, that's a separate conversation. Right now you're collecting their version.
- ·Write down what they say while it's fresh — or record it. Phones are good for this. You don't need anything fancier.
- ·If asking face-to-face feels like too much pressure — for either of you — consider letting our service text them one question every few days. Many people open up more easily over text than across a kitchen table.
Free printable
Get this list as a beautifully printable PDF
All 168questions, arranged by theme — print it, bring it to Sunday dinner, or keep it by the phone. We'll email it to you free.
No spam — a few question ideas and a reminder before the next holiday. Unsubscribe anytime.