Holding on and Letting Go- Traditions in the Teen Years

It’s that time of year—when Halloween ends, and we immediately start looking forward to our Turkey Day traditions and gearing up for Christmas, trying to squeeze as much as possible into a six- or seven-week window (6-7!). As we enter the holiday season, that familiar wave of nostalgia and excitement starts to roll in. We feel the pull of our own childhood memories—mixed with the ones we built with our kids when they were little.

And now, as they grow into teenagers, they start to dream up new traditions of their own—some that include us, and some that don’t.

And that hurts.

We’ve spent years—decades even—creating magic. Staying up late wrapping gifts, baking cookies, curating playlists, watching the same movies over and over, and setting the scene so our kids would look forward to this season with joy.

And they do. They just don’t necessarily want us in every memory. They can’t understand why we “still want to do everything as a family.” Hmmm… can’t imagine why. Maybe because ever since they entered our world, we can’t imagine a Christmas memory without them in it. For them, it’s the opposite—ever since they arrived, we’ve created the memories. And we’ve done such a good job that now, they want to try.

Maybe they’d rather go with friends to the places you used to take them, or skip something entirely—like the matching Christmas pajamas or the family photo shoot. It doesn’t mean we let them call all the shots, but let’s hear them out and give them some control. Maybe they can surprise the family with the pajamas this year, or siblings can pull names and buy each other their Christmas jammies.

As for the family photo shoot—they take pictures all day long! Let them curate the look. Let them have the final say on which picture gets posted or sent out to the family. And if they’re truly adamant about not sharing it, honor that—but still ask them to take the photo for the memory.

It’s hard getting dumped… and that’s kind of what’s happening. A breakup. They’re slowly breaking up with us throughout adolescence, often in small, subtle ways—like ripping off a Band-Aid. But during the holidays, it feels more like Steve Carell in The 40-Year-Old Virgin getting his chest waxed—“Ahhhhh Kelly Clarkson!!”

It’s such a nostalgic time of year that we can’t help but replay every Christmas past and see just how much has changed with our teens in one year. It’s sad—but also exciting. And also sad again.

It’s okay to be sad. But remember—we control the narrative. Encourage them to try new traditions. Lean into the change and go along for the ride.

Before you go all Olivia Rodrigo Deja Vu, feeling like your teen is taking their friends to all the places you used to —“Strawberry ice cream in Malibu!”—remember what they’re really saying: “These memories you gave me were so good—I want to share them with my people.”

It’s easy to take it personally, but let’s try to be prepared and get ahead of it. When holiday conversations come up in the next few weeks, start with curiosity:

“I can’t wait for _____ this December—what are you most excited for?”

Give them space to share their ideas. Maybe their friend’s family has a “Dessert Day” where they prep all their holiday sweets together, and your teen wants to join—or bring that idea home. Traditions start somewhere, and the best ones are often born out of love and connection.

Sometimes we pause a tradition for a few years, only to bring it back later—fueled by the nostalgia that brings everyone together again.

It’s easy to get stuck in the past and not enjoy the now, but one day this will be the past. 

The traditions from my teen years actually stand out more than the magical “believer” years. That’s a good reminder that what we do now leaves our teens with memories they’ll actually remember—not just stories that get passed down.

And it wouldn’t be my style if I didn’t find a way to bring my parents and sister into it—so here goes!

The holiday tradition I had with my dad and sister as a teen echoes the excitement of waking up on Christmas morning as a kid.

My dad worked in Cambridge, right near the Cambridgeside Galleria—the biggest mall I had ever seen. He would take my sister and me to work with him, and then we’d head to the mall to shop for my mom… on Christmas Eve!

Wild, right? The last of the last minutes. He’d basically give us free rein to buy her whatever we thought she wanted. Lerner New York—check! Victoria’s Secret—5 for $20, you know it! Bath & Body Works—hello, Plumeria!  He might make a stop at Kay Jewelers for something sparkly, and we’d always finish the day with a late lunch at The Cheesecake Factory.

The Cheesecake Factory in the ’90s was fine dining. Fresh-squeezed lemonade, my dad with his shrimp po’ boy—the bread!! Christmas Eve & The Cheesecake Factory is like The Fourth of July and Fireworks, they are bound together. 

Then we’d drive home in a food coma, then race inside to hide all the bags, as if any of those presents would be a true surprise. We’d go straight to my room to wrap everything while my dad kicked back. He had it made.

And now, as a mom, I can see that my mom had it made, too—a quiet house on Christmas Eve and probably a full day of solo returns ahead of her after she opened all the “treasures” we picked out for her.

My mom’s idea of a good time, on the other hand, was the Boston Ballet’s Nutcracker. My sister and I dreaded it—the tights, the skirts, the sitting still. I’d read the playbill just to figure out when intermission was so we could sprint to concessions. The best part of the night was the pre-ballet dinner at Bennigan’s. Yes, Bennigan’s! Another “fine dining” experience, all of my memories are tied to food! I didn’t even need to look at the menu, I knew I was ordering the Broccoli Bites as my entree!

We complained, but The Nutcracker was Christmas. And when my daughter was little, we listened to a recording of The Nutcracker book every night before bed in December—and for weeks after. I have to thank my mother for dragging us, kicking and screaming, into that memory.

We might not remember when a tradition starts or ends. I’m sure my dad’s tradition was born out of panic and a busy December, and I can’t remember my last trip to the Cambridgeside Galleria—but I know I didn’t realize it was my last one when it happened. 

We don’t always know why we hold some traditions tighter than others. But if we don’t make space for new ones, we miss the chance to see what new magic might unfold.

So before you cry in the car (or after—you’re allowed to), try to embrace their ideas, their friends, and their growing independence. It’s their life, too. There will be plenty of time for compromise down the road—but for now, enjoy them under your roof and soak up the new kind of magic that comes with it.

Because the holidays aren’t about the same traditions—they’re about the love that starts traditions and the memories we create. 

Enjoy the holiday season, and all the new and old traditions!

Your friend,

Caitlin