Before New Years, Ask Your Teen These 5 Questions to Deepen Your Connection

This Will Help You Understand Your Teen Better

The holidays feel different this year. Zac just returned from 2.5 months of travelling across Europe after graduating in the spring, and Sawyer is in his second year out on the East Coast. With both boys carving out their paths, face-to-face time has been rare, and while we talk often, the conversations tend to stay on the lighter side.

I don’t want them to think I worry about them every day, but, of course, I do. That’s something the loss of a child does to you. It changes how you think about connection, time, and the importance of the little things, like watching a hockey or football game together.

I’m looking forward to reconnecting with them this holiday season, not just as their dad, but as someone who genuinely cares about who they are becoming. And for other parents out there, I hope this can be a reminder to pause, reach out, and have those conversations that truly matter before the year ends.

It’s also a time to tell them how immensely proud I am of them. These boys have not had a typical carefree childhood. When your sibling dies by suicide, it changes your belief system and your purpose. They are both incredible young men, and don’t get enough credit for me being only partially insane.

Why These Conversations Matter

As parents, we often get caught up daily. We check in about grades, plans, or logistics. Those are the things important to us as parents. But when was the last time you asked your teen how they’re ‘really’ doing?

The holidays offer a unique moment to go beyond the surface. These aren’t conversations about solving problems or prying into their private lives. They’re about listening, understanding, and strengthening the bond that evolves as your kids become young adults.

Here are five questions I plan to ask my boys this holiday season. Maybe they’ll inspire you to start your meaningful conversations.

1. "What’s one thing you’re really proud of this year?"

This question isn’t just about achievements; it’s about helping them recognize their growth. It could be something as simple as making a tough decision, navigating a tricky situation, or even taking care of themselves.

I want Zac to reflect on the courage it took to travel Europe on his own and Sawyer to think about how he’s adapting to university life. Focusing on their wins, big or small, is a chance to celebrate who they are becoming.

2. "What was the hardest part of this year for you, and how did you get through it?"

Teens and young adults often carry more than they let on. My boys have faced challenges, even if they haven’t shared every detail.

This question allows them to share those struggles if they’re ready. And if they’re not? That’s okay, too. Just asking shows you’re there for them, no matter what.

3. "Is there anything you wish you could have done differently this year?"

We all look back and think about things we’d change. This question encourages reflection for teens and young adults and helps them see how they’re learning and growing.

It’s not about pointing out mistakes but helping them recognize how those moments can shape their future.

4. "What’s something you’re looking forward to next year?"

The end of the year isn’t just about looking back; it’s also about looking ahead. This question shifts the focus to hope, excitement, and what’s next.

Maybe Zac is already dreaming about his next adventure, or Sawyer has a goal he’s quietly working toward. Whatever they’re looking forward to, it’s a chance to encourage and support them.

5. "How can I support you better in the year ahead?"

This is the big one. It’s difficult to ask, but it shows humility and love. I don’t have all the answers, and my boys don’t expect me to. But asking this question gives them the space to tell me what they need, whether it’s advice, space, or just knowing I’m here.

Connection Matters More Than Ever

The truth is, I do worry about my boys every day. I think that’s just part of being a parent, especially after losing a child. But I’ve learned that worry doesn’t have to dominate the relationship. It’s about showing up, asking questions, and creating moments that matter.

This holiday season, I’m looking forward to simply being together. Maybe we’ll discuss these questions over a bite to eat or enjoy the moment while watching hockey or football. Either way, it’s about being present and telling them how much they mean to me.

For parents reading this, take the time to ask these five questions. You might be surprised by what your teen shares and how much it brings you closer.