Have you ever noticed how you can spend a lot of time with someone, work with someone every day, live with someone, or be related to someone, and still not know that person’s whole story?

I realized this a few years ago with a small group of friends I meet with through my church. We had been together for several years, talked about a bunch of different topics, and gone to a lot of events together. We were there for each other during the births of multiple kids, job changes, and challenging life situations. I thought I knew everyone really well. And I had assumed I had shared most everything with them too.

One season we decided to share our life stories with one another – what our home life was like growing up, past hurts, regrets, and successes, and key relationships in our lives. As we shared with one another, I was floored. I had missed so much! And suddenly a lot of things made more sense, where I saw how views and perspectives were deeply colored by past experiences. It was a powerful season.

Uncovering Stories Hidden in Plain Sight

It’s easy to live with the faulty assumption that time spent together equals knowledge about one another.

Do we really know each other – our past struggles, fears, hopes and dreams?

This is particularly true in families. We can assume we are closely-knit because we get together every holiday season, have regular conversations by phone or over a meal, or send gifts to each other. But, do we really know each other – our past struggles, fears, hopes and dreams?

One of my biggest regrets is not getting to know grandfather better. He passed away when I was a freshman in college. We had certainly spent a lot of time together. And, I had picked up bits and pieces of his story – how he grew up in Missouri, was a brave pilot during WWII, worked hard as a mechanic, and was a good father to my mother. But, there are so many missing details I would love to know. The funny thing is I look just like him too. When I look at pictures of him as a young father with infant kids, it’s unmistakable.

As we enter into this holiday season, each of us has a unique opportunity. Reports estimate that 107.3 million of us will travel from the day before Thanksgiving to the day after New Years. Whether we travel or not, this time of year often gives us a chance to connect with relatives and friends from different places and generations.

If we’re not careful, we could waste this opportunity. Most conversations tend to focus only on updates or debates. We update each other on our present situation, work stresses, or relationship status. And, it’s easy to get stuck in debates about politics or sports.

Six Story-Sharing Questions for this Holiday Season

Instead, I think it’s worth asking some better questions in the limited time we have with those closest to us this season. I especially think there’s a unique opportunity with those from an older generation. Here are six questions sure to help you share stories and shape a meaningful holiday-season conversation:

What’s the scariest step you ever had to take – was it starting a job, moving somewhere, getting married, or something else?
Looking back, what is one thing you did that made the biggest difference in your life?
If you could go back and do one thing over again, what would it be?
What insecurities have you had to wrestle with and work through?
Who had the most significant influence on your life? Why?
What is one piece of advice you would give me?

Whether you use these questions or not, make the most of this opportunity this season provides. Don’t settle for updates or debates. Dig deeper. It could lead to the best family gathering in years.