Joan Craven's Blog

As we grow older, conversations often circle around health – how we are feeling, what aches and what medical procedure is upcoming. These conversations matter. They offer honesty, trust, and a place to be vulnerable. But they are not the whole of who we are.

In the same way, it’s easy to fall into talking about news and what’s happening in the world. While these topics have their place, they can sometimes pull us away from one another.

There are moments when we can gently guide conversations in a different direction by asking questions that invite stories, memories and even some humour. And often, as we listen (with no interruptions) something stirs in us too: a memory returns, feelings resurface, or a part of us reappears.

If we choose just two or three questions, we open the door to conversations that feel richer and more nourishing. These exchanges remind us we are more than our ailments or the headlines of the day – they touch on the deeper layers of who we’ve been, who we are now, and the shared moments that are unfolding and continue to shape us.

Questions

1. What’s something you once did that you never expected to enjoy but you loved.
2. What’s something that made you have good belly laugh recently?
3. If you could instantly master a skill, what would it be?
4. If you could have a long lunch with someone living or not, who would you choose?
5. What’s something you’re looking forward to- big or small?
6. What TV show would you want to be in and why?
7. When you were a kid, what was the name of your favourite stuffed animal or toy?
8. If you could attend any celebrity wedding, who would it be and why?
9. What’s the weirdest gift you ever received?
10. At your present height would you choose to be 6 inches shorter or 6 inches taller?
11. If you could have a lifetime supply of anything, what would it be?
12. What’s the worst date you’ve ever been on?
13. Did you ever get in trouble at school and if so, what for?
14. If given the opportunity would you travel in time – past or to the future?
15. What’s your funniest childhood memory?
16. Would you rather spend the day without your phone or without speaking?
17. Did you have an imaginary friend as a kid?
18. What is your all-time favourite television series or episode and why?
19. If you woke up as your 16-year-old self tomorrow, what would you do?
20. What was your first magazine subscription?
21. What’s the first thing you’d buy if you won the lottery today?
22. If you could travel anywhere in the world right now, where would you go?
23. What’s the word or phrase you learned as a kid and have been saying all your life?
24. If you could use magic to do one mundane task for the rest of your life, what would it be?
25. Have you ever made a prank phone call?
26. What did your childhood bedroom look like?
27. What moment in history do you most vividly remember?
28. Do you have a favourite family tradition to keep alive?
29. What has been the most impactful invention during your lifetime?
30. As a child what did you do for fun?

I hope you have fun with these!