Raise your hand if you’re already dreading the annual, predictable, tired prompt at your upcoming Thanksgiving dinner this week: “Let’s go around the table and say what we’re grateful for…”
It’s fine, but, in part because it’s so predictable, this question rarely sparks specific, juicy, unexpected answers.
In case you’re gathering this week or soon with family — chosen or inherited — here’s a cheat sheet of 40 questions that range from playful to reflective that you can ask instead… fully ready for you to use.
Some of these questions come straight from you and our GROUP HELP Session!
Winter warmups
“What’s been your harvest this year?” – Amy
“What has made you laugh out loud recently?” – May-Ling
“What’s the most unexpectedly delicious food combo (so, two ingredients) you’ve discovered that sounds weird but tastes amazing?” (This one comes from my Instagram and the comments are hilarious.)
“What’s your anti-pet peeve? (i.e. a tiny thing that brings you joy or satisfaction)” – Jessie
“What’s a hobby you don’t have… but desperately want someone else at this table to teach you?”
“What is the warmest place you remember from childhood?” – Melissa
“What’s your favorite holiday tradition?” – Cath
“What fictional character would you invite to Thanksgiving dinner and why?” – Courtney
Light, fun, and playful questions (with some depth)
“What’s your most controversial low-stakes opinion?”
“What’s a tradition you fiercely protect when you’re not home?”
“What’s the best tiny decision you made recently?”
“What brings you joy right now? (Draw your answer.)” – Jane
“How do you inject a snippet of fun into your day?” – Andrea
“What dish holds a memorable moment for you?”– Makena
“What’s the best gift you received this year (present company excluded) and who gave it to you?” – Kate
“Gathered here today, we are a living family tree. What kind of tree are we? Why?” – Laurel
“Tell us your juiciest piece of NON-FAMILY gossip from the past year. It’s not allowed to involve ANY family, whether or not they’re here in the room with us.” – Eng Seng
“What’s the naughtiest thing you’ve ever done…that was worth it?” – my daughter asked this at a family dinner recently and it lit up the evening.
Reflective year-in-review questions
“What’s a plan you made this year that went totally sideways, but in a good way?”
“What’s the biggest risk you took this year?” – Kathy
“What song would be your theme song for this year?” – Radka
“What’s the best thing and hardest thing that happened this year?” – Jackie
“What’s your biggest surprise this year?” – Elisa
“How have you helped someone out this year?” – Nick
The people who changed your year
“What’s a moment from this year when you surprised yourself?”
“What’s one moment from this year when you felt exactly where you were supposed to be?”
“Who has made something hard feel less lonely this year?”
“Who made your life more fun this year?”
“When did you feel most seen or supported in the last year?” – Mirit
“Who, in your life, surprised you the most this year?” – Cynthia
“What have you seen someone do this year that had a positive impact on your outlook on life?” – Susan C
“What is a part of yourself that you derived from your dearest mentor?” – Chelsea
Deep cuts
“What’s something you did this year that the people at this table would be genuinely surprised to learn?”
“What’s a compliment someone gave you this year that you still think about? What made it so impactful?”
“What’s a moment when you realized you were becoming more like someone in this family?”
“When did someone see something in you that you didn’t see in yourself?” – Mirit
“What’s the best thing — and the hardest thing — that happened this year?” – Jackie L
“What’s most helpful to you during transition times?” – Marcia B
“What are you letting go of from this year, and what are you carrying into next year?” – Jaime S
“What are you grateful for from Mary’s [or if someone in your group has passed] life?” – Traci W, who shared that her mother, Mary, passed away in September.
As you head into the end-of-year gatherings, try one of these questions with a group you want to connect. Make these questions specific to your people and your moment, and they’ll do even more work for you.
And in the comments below, what question would you add to this list?
As always,
Priya
Wonderful! Thank you for these!
Thanks for so many magical questions.
I’m the moderator of a governing board for a small organization and we started this month’s meeting with the magical question “what’s your favorite way to eat a potato” and the energy it generated around the room and the things we learned about each other were, well, magical!
I’m saving magical questions to a notes app on my phone so I have them handy for whatever group I’m in that might need a little catalyst for group-ness