Start a new holiday tradition: Conversations to remember

My grandmother, Esther, was wonderful. I remember her as strong, caring, and hardworking. I remember taking friends to the creamery where she worked. She handled large milk containers with ease and manipulated the large steam hoses like they were nothing. Of course, the best part was being taken into the freezer and being allowed to pick out an ice cream bar. Pretty cool when you are six.
During the holidays, she had only one request—that for two hours at some time during gathering, everyone would be in the same room for a conversation. No games, television, or distractions were allowed. Only one person could speak at a time, and the youngest person got to start. After that person finished, he or she would pick the next person to speak. Sure, people got excited and jumped in from time to time, but for the most part the conversation flowed as intended. Those where the conversations everyone in the family remembers fondly, even though it took the iron will of my grandmother to make it happen.
You can buy sets of cards with questions that can get the conversation started, but it’s more fun to create your own. Start with a few—things you’re curious about or would be fun to learn what your family thinks—and ask family members to suggest others. People always love the questions they come up with on their own.
Here are some possible questions to get you started. It’s fine if people take the conversation in different directions—that’s part of the fun.

What did you like best about your favorite room growing up?
What did you collect—stamps, dolls, Star Wars characters…?
What were your favorite games and who did you play them with?
What was the neighborhood like where you grew up?
What was magical about your childhood?
What do you remember and like about your grandparents?
Ten years from now, what would you like to remind yourself about life?
Who is the most famous person you’ve met or what famous person would you like to meet someday?
What was the biggest moment that you missed out on?
Who were your best friends? What were they like?

Given the pull of our lives these days, you will probably need someone to say, “I want to do this, and I want everyone to join in.” Give people some advance notice on when you would like to do this and perhaps start with 30 minutes and one question if it is a departure from the normal way that your family interacts.
It seemed easy for my grandmother to get everyone into the same room and paying attention. I wonder how she would have handled technology. Back then, it was only the television and there were only three channels. Now, we’ve got smart phones, tablets, computers, video game consoles, and umpteen TV channels. Somehow I think she would have pulled it off—the question is: can we?