Part 3: Engage in Conversations That Matter
The tween years are often described as a turbulent time for both children and parents. As your child navigates this stage of growing independence, developing interests, and testing boundaries, you might feel the gap between you widening. The conversations that once came so easily—about their favorite toys, their dreams of becoming astronauts, or what happened at school that day—suddenly seem harder to come by. Instead, the dialogue becomes a back-and-forth exchange of logistical discussions: "Did you finish your homework? Did you take out the trash? What time is your practice?" These routine conversations are necessary, of course, but they don’t always foster the kind of connection you’re hoping for.
In these years, your tween is not only growing physically but emotionally, mentally, and socially. They are processing new thoughts, emotions, and experiences that may feel overwhelming to them, and yet, they may be reluctant to share. The floodgates of emotion are often still behind a wall they’ve built for themselves, and they may not always know how to articulate what they’re feeling. As a parent, this can feel isolating, especially when you want to be their safe space, their confidante, the one person they can turn to when they need to be heard.
However, the tween years also offer a beautiful opportunity to engage in deeper, more meaningful conversations. These moments of reflection and connection can help your child better understand themselves and their world. They need more than just the "surface-level" conversations about schedules and chores. They need a space where they feel safe to explore their thoughts and feelings—where they know you’re truly listening and you’re present with them in the most authentic way.
In this third part of the series, we’ll dive into how you can create meaningful, engaging conversations with your tween. These aren’t just casual chats—they’re the kinds of conversations that foster deeper understanding, empathy, and connection.
Talk About Values: Foundations for the Future
As your tween grows, they begin to experience the world in new ways. They start to question their beliefs, the values they hold, and their place in the world. It’s a time when they begin to understand the difference between right and wrong, fairness and injustice, kindness and cruelty. They may be influenced by their friends, social media, and the messages they see around them, but at the core, they are developing their own moral compass.
This is where you, as their parent, can provide invaluable guidance. It’s not about dictating what they should believe—it’s about having honest, open conversations about values, and allowing them to explore what’s important to them. This can be a powerful tool for helping your tween feel grounded as they navigate the chaos of adolescence.
The next time you’re sitting down for a quiet dinner or driving together to practice, take a moment to talk about the things that matter to both of you. Ask questions like:
“What’s something you’ve always believed is important, and why?”
“How do you handle challenges or things that are hard in your life?”
“What kind of person do you want to be?”
These aren’t just questions to fill the silence—they’re conversations that will help your tween start to solidify their values and beliefs, and in turn, will help them feel more confident in who they are.
One evening, I sat down with my daughter, Lucy, after a long day of running errands. She’d had a tough week at school—lots of drama with friends and a challenging test she didn’t do well on. As I made dinner, I casually asked her, “What do you think is more important—being nice, or being honest?” I didn’t expect much of an answer, but her face softened, and she said, “Being honest, I guess. But sometimes honesty can hurt people’s feelings.”
We spent the next 20 minutes talking about the balance between kindness and honesty—how you can be truthful without being cruel, how your words have power, and how your actions reflect your character. This wasn’t a lecture. It wasn’t a “life lesson” moment. It was a conversation that allowed her to express her thoughts and challenge her ideas. And as a result, I saw her leave the table with more clarity about who she wanted to be.
Share Your Memories: A Bridge Between Generations
The tween years are a time when your child is beginning to see you not just as a parent, but as a person—someone who had their own experiences, challenges, and growth before they were born. They are starting to recognize that you, too, were once young and figuring things out just like they are now. Sharing your own stories—especially from your tween and teenage years—can be a powerful way to build empathy, connection, and trust.
These stories give your tween a glimpse into your past, helping them understand that you’ve been where they are and that you, too, have navigated difficult emotions, friendships, and challenges. By sharing these experiences, you create a sense of solidarity. Your tween sees that you’re not just a parental figure, but someone who understands their struggles.
One evening, while folding laundry, I started telling Lucy about the time I failed a big math test in middle school. I shared how devastated I was and how embarrassed I felt, but also how that failure taught me resilience and the importance of asking for help when I needed it. I didn’t make it a lesson. I simply shared my vulnerability.
She stopped what she was doing and said, “Mom, I failed my math test this week, too. I thought I was the only one.” That small moment of connection was huge for us. It didn’t solve her anxiety, but it reassured her that it’s okay to fail, and that failure doesn’t define you—it’s how you get back up that matters.
Create a “Question Jar”: Spark Reflection and Curiosity
Sometimes, the best conversations come from a little nudge. Your tween may not always feel comfortable initiating deep discussions, but if you offer a safe, fun way for them to start sharing, it can open the door to meaningful connection.
A “question jar” is an excellent way to engage in thought-provoking, meaningful conversations. The idea is simple: write down a variety of questions—some fun, some deep—on small pieces of paper, and place them in a jar. Each week (or whenever you feel the need), take turns drawing a question from the jar and discussing it together.
The beauty of the question jar is that it offers a chance to talk about a wide range of topics, from lighthearted to serious, and gives both you and your tween a platform to explore ideas you may not have discussed before. Questions can range from:
“What’s your biggest dream for the future?”
“If you could meet anyone in the world, who would it be and why?”
“What’s your biggest fear, and how do you cope with it?”
These types of questions create an opportunity for your tween to reflect on their emotions and thoughts, and for you to learn more about what’s going on in their world. It’s a great way to understand the things that matter most to them and to show that you care about their feelings.
Lucy’s school sent home a question jar at the beginning of the school year, and some of our most heart-to-heart conversations have come from it. It’s been a gentle way for us to dig deeper without feeling like we’re “forcing” the conversation. It’s fun and lighthearted at times, and deeply moving at others.
The Heart of It All: Listening and Being Present
The foundation of all these conversations is trust. When you create an environment where your tween feels comfortable sharing their thoughts and feelings, you’re building the kind of relationship that lasts. When they know they can come to you with anything—and that you will listen, not judge—they’ll continue to turn to you, not just now but in the years to come.
So, the next time you sit down with your tween, remember that it’s not just about talking—it’s about listening, understanding, and showing them that they matter. And most importantly, it’s about creating a space where they can truly be themselves.