Muddy’s Blog

A Well Seasoned Conversation This Thanksgiving

A Well Seasoned Conversation This Thanksgiving

Happy Thanksgiving! It's one of my favorite holidays -- gathering around a meal with family and friends is my jam-- but also one that can easily fall into a scripted pattern.  

Conversations can especially seem bland and lacking in flavor.  Old family dynamics are at play as well as the normal awkwardness of conversing with people you only see a few times a year (or less!).  It can be really easy to fall into a conversational rut and miss some excellent opportunities to truly get to know these folks better.  As I get older, I'm especially aware that the window of opportunity with some relatives is closing rapidly and there will be much I regret not asking them.

Instead of the scripted "how's work/school/the weather?" (or eye rolling a relative with whom you disagree), pepper your conversation with open ended, unexpected questions to get to know these people that, whether we chose them or not, are an important part of our lives.  

To get you started, we've got a few flavorful prompts and questions you can use to get past the banal.  Hopefully you'll get some laughs, maybe some tears, and if nothing else, get to know some different facets of these familiar faces.


  • What's something this year you're really proud of?
  • What did you really enjoy when you were my age?
  • What challenges did you have when you were my age?
  • Is there a historical event that made a big impact on your life?
  • If you had a totally different career, what do you think you'd choose/would've chosen?
  • How many generations back can you name, first and last names (ie: parents, grandparents, great grand parents, etc)
  • If you could teleport to visit anywhere immediately, where's the first place you'd visit?
  • What's the best job you ever had?
  • What's the worst job you ever had?  Would you do it again?
  • What's a supposedly fun thing that you'll never do again?
  • What's the best gift you've ever received?
  • Who is someone who made a really positive impact on your life?
  • You can invite any 3 people, living or dead (or even fictional!), to a dinner party-- who and why?
5 Questions Especially Fun for Young Kids (but not JUST kids!)
guess what, kids sometimes like to talk about things other than how school is going!
  • What animal do you think it'd be fun to be for a day?
  • Would you rather be invisible or able to fly?
  • When did you feel really brave?
  • If you were in charge of a whole day, what would you do?
  • What's the most adventurous thing you've ever eaten?  (be sure to ask for the story/context behind it!)
3 In-Case-of-Emergency
for when you're in a hot conversation and falling into the trap of demonizing someone you disagree with (hey, it happens)
  • I'd love to understand more about why you think/believe that
  • That's interesting-- is there a particular experience you've had that makes you feel that way?
  • You obviously care a lot about this; what have you found surprising or interesting as you've learned more about it?