37 Questions for More Intentional Holiday Conversations
This year, we’ve invited you to rethink some things with us. We’ve written about how to be more thoughtful and purposeful in taking care of ourselves, our planet, and our financial futures.
And at the root of all of that is a desire to take good care of each other, too.
Here’s the deal: We’re so damn thankful for you all. And after another tough year, we’re feeling some serious gratitude for health, stability, and connection.
And, TBH, connection is something we could all use a little (or a lot!) more of. That’s one of the reasons we L-O-V-E the holiday season. From November to January, we’re all warm and fuzzy thinking about all the opportunities to live, laugh, love (sorry) with our friends and family.
But, let’s be honest. Sometimes holiday connection feels just a tad… forced.
In those awkward moments, we tend to rely on cookie-cutter, small-talky, “Soo… how’ve you been?’ type questions:
What’s new with work?
How are the kids?
When’s the wedding?
See any good movies lately?
Ugh. Surely there’s a better way to build deeper connections with our people, right?
Absolutely there is.
37 Questions for More Intentional Conversations
This year, try some of these questions to avoid all those awkward, one-hit-wonders and be more intentional in connecting with your friends and family. Consider putting them on notecards and placing one question at each seat around the holiday table!
If you could learn one new personal skill, what would it be?
What’s an article of clothing that if someone wore it on a date, you’d immediately walk out?
What are you rebelling against right now?
What’s the best piece of advice you’ve ever been given?
What’s your most used emoji?
If you could eliminate one thing from your daily routine, what would you choose?
What’s the worst haircut you ever had?
What’s the best purchase you made this year?
If you could listen to a song again for the first time, what song would you pick?
What did you name your car?
What’s the worst advice you’ve ever been given?
What’s the best gift you’ve ever been given?
How did you find out Santa Claus was fictional?
What are you most likely to be famous for?
If you could only keep three apps on your phone, what would they be?
What holiday tradition is your favorite?
If your life had a theme song, what would it be?
What’s your favorite piece of clothing?
If you were left on a deserted island with either your worst enemy or no one, which would you choose?
What’s the best compliment you’ve ever received?
What’s your favorite weird food combination?
Who would you add to Mount Rushmore and why?
If you could commit a crime and get away with it, what would you do?
What’s your favorite room in your house?
What’s the biggest risk you’ve ever taken?
If aliens landed on Earth tomorrow, would you go back to their planet with them?
What’s one meal or dish that reminds you of home?
If you wrote a book, what genre would it be?
What breed of dog would you be?
Have you ever successfully kept a New Year’s resolution? What was it?
What’s a fictional world or place you’d like to visit?
Who is your longest friend and how did you meet?
What’s your earliest holiday memory?
Is there a charitable cause you regularly support?
What’s one thing you always do before going to bed?
What’s your favorite guilty pleasure show?
What’s the most recent photo in your camera roll?
We want to get to know you, too!
Whether you’re ready to get into the real estate game or just want to chat, drop us a line and answer one of these questions—and ask us one, too! We’d love to hear from you.
