What Your Teen Is Desperately Trying to Tell You (But Can’t)

Don’t Wait For a Crisis to Start Listening

I used to think I was doing all the right things.
I asked how her day was.
I set boundaries.
I stayed involved.

But when I asked my daughter Maddie how she was really doing, she’d often shrug and say, “I don’t know.”
Or “I’m fine.”

She wasn’t.
And I didn’t know how to see past those words until it was too late.

The Night Everything Changed

Maddie was 14.
She was bright, funny, and deeply loved. Her light drew people in: friends, teachers, and even strangers.

But like so many teens, she carried more than she let on.
She’d lived through a family divorce, financial stress, and multiple school moves. Her world shifted too many times, too fast.

One night, she snuck out to a party. I found her crying in a closet—overwhelmed, scared. I brought her home, tucked her into bed, kissed her forehead, and said, “Tomorrow’s a new day.”

That night, Maddie tried to end her life for the first time.
It wasn’t the last.

We tried therapy. We tried talking. I tried structure, more rules and involvement, thinking it would help.

But the harder I pushed, the more she pulled away.

What I Didn’t Understand Then

Maddie didn’t need me to fix her.
She needed me to sit beside her in the mess.
To listen without rushing in with advice.
To hear what she couldn’t find words for.

When teens say “I don’t know,” it’s not because they don’t care.
It’s because they’re overwhelmed. Or afraid. Or they simply don’t have the emotional language to explain what’s going on inside.

What Maddie was really saying, but couldn’t was:

“I don’t feel safe opening up right now.”
“I’m afraid you’ll be disappointed.”
“I’m lost and I don’t know how to ask for help.”

What I’d Tell Any Parent Now

If your teen is pulling away, going quiet, or shutting down, it doesn't mean you've failed.

But it may mean they’re struggling in ways they don’t know how to share.
Here are three things I wish I’d done sooner:

1. Lead with Curiosity, Not Pressure

Instead of “What’s wrong?”
Try: “What’s been the hardest part of your day?” or “Is there something you’ve been thinking about that’s hard to talk about?”

Open-ended questions can feel like an invitation instead of an interrogation.

2. Give Them Permission to Take Their Time

Say this:
“We don’t have to talk now. But I’m here. Anytime.”

Those words are important. You’re not forcing the conversation; you’re creating space for it to happen when they’re ready.

3. Let Someone Else Step In (Without Stepping Out)

Sometimes, teens need to talk to someone who isn’t their parent. Someone neutral, safe, and outside the family dynamic. Someone who’s not there to judge or diagnose but just to get it.

We started The Mentor Well because Maddie needed that kind of support, and too many teens still do.

This Mission Was Born From Love

Losing Maddie was the most devastating thing I’ve ever lived through.
But her story became my reason to build something that didn’t exist when she needed it most. It’s a space between therapy and parenting, where teens can talk, explore, and heal with the guidance of a mentor who leads with empathy, not authority.

Mentorship isn’t a replacement for parenting.
It’s a bridge.
It’s someone saying, “You’re not broken, you’re just figuring things out, and I’m here while you do.”

If Your Teen Is Quiet, Withdrawn, or Always “Fine”…

Please don’t wait for a crisis.
Sometimes, silence is the loudest signal of all.

We built The Mentor Well to catch kids in that in-between space. The ones who don’t want therapy. The ones who seem “okay” but aren’t. The ones who, like Maddie, just need someone to help them feel seen.

🙏 Learn more about mentorship for teens
📞 Book a discovery call
📥 Download the “I Don’t Know” Conversation Starter Toolkit

You’re not alone. And neither is your teen.