Heart Check-In Guide: How to Have Meaningful Conversations with Your Teens
There’s not always an easy roadmap for how to have meaningful conversations with your kids, and this can especially feel true in the teenage years.
2 min read
Legacy Stone December 8, 2025
Have you or anyone else in your family found yourselves giddy with excitement for the holiday season? Almost as if you’ve already established a picture in your mind of each holiday celebration: fixing Christmas dinner, telling the story of Jesus, opening presents around the fire.
You can practically see it.
And then you fix the Christmas dinner all by yourself while everyone watches the football game. Or maybe when dinner is over, instead of cleaning up together, you peek around the corner to see everyone sitting on the couch with their phones in hand.
Let us bridge the gap for those moments this year. If you find yourselves in a holiday lull, or see the direction that everyone is headed where you can unplug, start with these simple family conversation starters.
Grab one of your teenagers, pull in a young adult child, or sit with your grandparent as they finish up the meal at the table and let the conversation start itself:
These questions encourage family members to reminisce and continue sharing the important family stories.
These will allow a natural pause of reflection, both personally and together.
Remember to have some fun! Get the kids (young and old) involved and these, spark the conversation and see where it takes you all!
If you're looking to grab a few more in-depth reflection questions, read up on these 22 reflections and implement them in your next conversation or family meeting!
All of these family conversation starters and categories have one thing in common: culture. And the first step to creating intentional, attractive culture for your family is to have conversations that are culture-forming about legacy, reflection, goals and much more!
If you feel as though your family is ready or even in need of something more tangible for family culture- something that clearly defines it for your family, sets you apart from the stereotypical buzzwords of "culture" according to today’s society and holds your family accountable to living on purpose, the Winning Family Culture Study is the next step.
There’s not always an easy roadmap for how to have meaningful conversations with your kids, and this can especially feel true in the teenage years.
As a Christian parent, you want your child to hold to godly values… but how exactly does that happen? It’s great to model values in your life, but...
Our family gathered last week to celebrate an important milestone in the life of our son. We attended the ceremony, flew siblings down to be with us,...