10 Things I’d Ask Every Parent at a Dinner Party (But Probably Won’t)

Because your teen is struggling more than you realize

For all the parents still trying to do things the old way: keep it superficial, fix the behaviour, avoid the big emotions: these are 10 questions I’d like to ask you.

But probably won’t.

Because these aren’t small talk questions. They’re gut checks. They’re for the parents who think silence means everything’s fine. For those who assume that if it ain't broke, don’t fix it.

Here’s another wake-up call.

If your teen isn’t talking, how would you even know it’s not already broken?

And if you can’t answer at least half of these questions honestly, how can you really look out for them, if you’re living with your head in the sand?

These are the emotional check-in questions I wish more parents had the courage to sit with. They’re not about blame. They’re about waking up before your kid stops trying to be seen.

1. What’s your teen proud of that you haven’t asked about?

If you don’t know what lights them up privately, what they quietly celebrate when no one’s watching, then they may have stopped expecting you to care. That kind of disconnection grows slowly and hurts deeply.

2. When’s the last time they looked you in the eye without flinching?

Avoidance, withdrawal, or guardedness in eye contact often means emotional trust has eroded. If they look through you instead of at you, it might be time to rebuild your side of the bridge.

3. Would they come to you if they screwed up?

If you’re the first person they fear disappointing, or if your reaction feels bigger than their mistake, they’ll go elsewhere. Or worse, they’ll go inward and bury it.

4. What do they think you’re ashamed of in them?

Every child makes assumptions. If your disappointment has ever lingered, even subtly, they’ve likely internalized a version of "not enough."

5. When was the last time they cried… and you noticed?

Not just tears, they tried to hide. But any sign of overwhelm, shutdown, or softness. If it’s been a while, it might not mean they’re fine. It might mean they no longer feel safe around you.

6. Who do they feel safest with, and is it really you?

If you’re not the one they turn to when the wheels fall off, ask why. Sometimes the answer is about them. But often, it’s about how you respond when they need you most.

7. What don’t you want to know?

That thing you’re hoping isn’t true. The possibility you don’t want to entertain. Ignoring it doesn’t protect them. It just isolates them.

8. Have they ever felt completely alone… while living in your house?

This is one of the heaviest ones. Being under the same roof isn’t the same as feeling held. Kids can feel emotionally abandoned even when parents are physically present.

9. What’s their biggest fear right now, and have you asked or assumed?

Assuming they’re just worried about school or social media misses the depth of what many teens are carrying. Fear of failure, rejection, identity, and even despair. You can’t comfort what you don’t acknowledge.

10. What is the one thing they'd tell you, if they knew you'd listen?

Not just hear. Listen. With stillness. With open hands. Without rushing to fix, justify, or minimize. Because when they feel like you can hold their truth, they might finally speak it. Ask not to fix or defend. Just to be the one they can finally say it to.

Why these dinner table questions matter

They’re not interrogation, they’re invitations.

I’ve been there. Sometimes the last thing you want to do is poke the bear. There’s a relative calm in the house, and sure, it’s not joyful, but it’s not erupting either.

You don’t want to stir the pot. Or kick the hornet’s nest. Or unearth something you don’t feel ready to hold.

But if you believe silence is safety, I’m here to remind you it’s not.

I receive about a dozen messages a week from parents who tell me these posts have changed how they present themselves. That they’re more deliberate. Since they’ve started listening first, the conversations are starting to shift.

Not perfectly. But honestly.

They say things like,
"We’re still figuring it out, but we’re finally talking again."
"She told me something last week she never would have six months ago."

That’s the power of choosing curiosity over control, of being someone safe to open up to.

As much as you’re trying to figure your teen out, they’re doing the same with you. Watching how you respond. Testing whether you can handle their truth.

So many parents operate from a quiet “if it ain’t broke, don’t fix it” mindset.
Yet if your teen isn’t talking… how would you even know?

The bigger question: even if they won’t answer, wouldn’t you want to know?

Seriously, it’s not just about them responding. It’s about who you become while you wait.

It’s about sitting with the discomfort. It’s about choosing to hold space when it would be easier to shut it down. It’s about letting your teen see you trying, even imperfectly.

And if that feels too big to do alone, you don’t have to.

At MentorWell, we help parents build the tools, the language, and the emotional stamina to show up differently. Not perfectly. Just with presence, patience, and purpose.

And sometimes, they need an outside set of eyes and ears that say, “I see you and I hear you.”

So when your teen finally does speak… at least someone will be there to sit with them.

Want support? Guidance? Or just the next right step?
See if mentorship is a viable solution for your family.