This is one of the hardest shifts in parenting:

The child who used to talk non-stop now barely says a word.
The one who once came to you for every little thing now keeps most of their world to themselves.

Many parents quietly wonder, “When did we stop being close?”

Teenagers are growing, changing, and figuring themselves out, and as they do, it is common for the relationship with their parents to feel distant or strained. It is not that they don’t care. They just don’t always know how to open up or where to start.

But the good news is this holiday period gives you a window, a bit more time, and fewer distractions so you can reconnect with your teen because sometimes all it takes is the right question to open a door.

Here are 5 conversations you can start with your teen during the holidays to help you reconnect with them.

1. “What is something you wish adults understood about you?”

This question gives your teen permission to speak freely without correcting them.
 You might hear things like

  • “I’m not lazy; I just get overwhelmed.”
  • “I don’t always know how to say what I’m feeling.”
  • “I wish you’d ask instead of assuming.”

The goal here isn’t to debate their answer but to understand their lens. You may discover what they have been carrying silently, and it helps you see them beyond surface behaviours.

Pro tip: Ask this while doing something casual like folding laundry or taking a walk. Teens tend to open up when there is no pressure to “talk.”

2. “How do you feel about how things went this past school year?”

Don’t frame it as a performance review. Think of it as a chance to reflect with them, not at them.

 Listen for patterns. What drained them? What made them proud? What did they enjoy?
 This kind of reflection helps teens build self-awareness without fear of judgment.

You are planting seeds of responsibility here. Not by scolding, but by asking questions like

  • “What helped you stay focused?”
  • “What do you want to do differently next time?”
  • “Did you feel supported, or did you feel alone?”

This is also a great moment to affirm their efforts, not just their achievements.

3. “What kind of adult do you want to be one day?”

This question sparks vision. Not “What do you want to be?” (which can feel like pressure), but “What kind of person?”

You might hear things like

  • “I want to be kind but also successful.”
  • “I don’t want to be stressed like most adults I see.”
  • “I want to make my own decisions.”

This conversation helps them connect the dots between now and later. You can gently guide them to see how habits they are building today feed into that future.

Pro tip: Share a bit of your own teenage dreams, including the ones that changed. It makes you human and relatable.

4. “What do you think about how we talk to each other in this house?”

This is about your relationship, not just their behaviour. Teenagers are sensitive to tone and fairness. They often won’t say anything most times unless asked directly.

Questions like:

  • “Do you feel heard when we talk?”
  • “Are there things I do that make it harder for you to open up?”
  • “What is something I do that helps you feel safe?”

You might be surprised by what they say. Don’t defend yourself in the moment. Just listen. Take notes if you have to. And circle back later.

5. “Is there anything you want to try or learn this holiday?”

This is how you show support without pushing your own agenda. Teens often want to explore new things but hesitate because of fear, self-doubt, or lack of structure.

Whether it is:

  • Learning to drive
  • Trying photography
  • Starting a YouTube channel
  • Reading a certain book
  • Getting a small holiday job


Keep Showing Up

Feeling disconnected from your teen can be painful, especially when you remember how close you used to be. But that distance doesn’t have to be permanent.

Your teenager may not always show it, but they still care what you think. They still want to feel understood. 

That is why these conversations aren’t about fixing your teen. They are about learning who they are becoming. You may not get deep answers right away, and that is okay. What matters is showing up, asking, and listening, even when it feels awkward at first.

You have got this.