When I was a kid, one of my favorite Christmas traditions was the Advent calendar my parents would purchase for us each year. We always opened the little window on the calendar in the evening before going to bed, so there was plenty of time for excitement to build. What would we uncover when we peeled back that paper flap? Would it be a picture of candy, or a toy, an image of one of the members of the Holy Family or perhaps a reindeer or Santa. We never knew, but we approached the ritual each evening with giddy anticipation, hoping what we uncovered would delight us.

Recently, I began thinking about the simple tradition of the Advent calendar and the metaphor it is for so much of life. That became abundantly clear to me over the Thanksgiving weekend.

It’s no secret that I’ve met some well-known people, or people connected to well-known people, throughout my life. Some time ago I mentioned my friendships with an insomniac author, a schoolteacher who hosted potluck suppers every Sunday evening followed by storytelling into the wee hours, a man who sculpted tree spirits, another who lived in a tree house, assorted artists, journalists and singers, an older man who hosted raucous poker games at a moment’s notice and many other interesting characters. Some of these folks eventually found some measure of fame or fortune. All of them introduced me to other interesting people, some of whom were well-known.

There is a point to all of this. How often do we do nothing more than scratch the surface with others in our lives? How frequently do we fail to look beneath the surface, preferring to keep our relationships superficial?

OK, all that’s a bit heavy, but the man who sculpts tree spirits, Keith Jennings, and his family, sans daughter Dorian who is enjoying a year of studying abroad, were on the island over the weekend and, as usual, they brought friends. Dorian’s best friend, Hana, was one of the bunch that accompanied the family for the holiday. Hana lives with her mother and siblings less than a mile from the Jennings clan. A theater major at University of North Carolina Greensboro, Hana is the personification of a lithe, unaffected, charming and completely disarming young woman, and has some serious show business genes.

You see, she’s the granddaughter of Kris Kristofferson and his second wife, Rita Coolidge. Yes, this guileless young woman is the descendant of he with the gravelly voice, rugged good looks and a history of hard living. He has shelves full of awards, including Grammys, a Golden Globe for best actor in “A Star is Born,” a handful of Academy of Country Music awards, a Country Music Association award and an Academy Award nomination for best motion picture soundtrack in 1985 for the movie “Songwriter,” which lost to Prince’s “Purple Rain.” He isn’t an intellectual lightweight either. He and a former boss of mine were friends while Rhodes Scholars at Oxford University in England, and apparently maintained that friendship until my boss died. But that’s a story for another day. Hana’s grandmother, Coolidge, is best known for her string of country pop hits in the 1970s and early 1980s, including “We’re All Alone,” “All Time High,” “Higher and Higher” and “I’d Rather Leave When I’m in Love.”

We all hear stories of young people who are descended from show business families running amok, fueled by nothing other than their trust funds and heavy senses of entitlement. Yet, I had the opportunity to meet a woman whose lifestyle is the antithesis of that mindset — Hana is busy studying her craft, finishing college and enjoying her friends and family.

Of course, had I not met Keith, and subsequently his wife, Katherine, none of this would have been possible. But my friendship with the Jennings family began with Keith’s dad, the late Bill Jennings, who was the aforementioned host of those raucous poker games, and took great delight in driving his “gals” around to Saturday morning yard sales and scaring us with his fascinating motor skills.

So as I sat with the family, and Hana, in the backyard of their vacation rental, we swapped stories as only old friends — who had both celebrated and mourned together — can do. Our ties now include three generations of family, and our friendship would never have happened if I hadn’t been taught to live life with happy expectations and to always peel back the flap and check to see what’s beneath the surface.