You know how it goes - you ask: “How was your day?”

They respond: “Fine.” Even though body language, tone of voice, and your Spidey-sense all tell you it was anything but — Fine.

End of conversation. Beginning of frustration.

If you’ve got a teenager, you know this wall. If you’ve got a spouse who just worked a 12-hour shift, you know this wall. If you’ve got a kid who just got off the school bus with that look on their face — the one that says something happened, but they’re not telling you — you know this wall.

“Fine” is a locked door with no handle on your side.

And most of us respond to it one of two ways: we push harder (“No really, how was it?”) or we give up (“Okay then”). Neither works. Pushing makes them retreat further. Giving up confirms they were right not to share.

Here’s what I’ve learned after many, many years of sitting across from people who didn’t want to talk.

The question “how was your day?” is broken. It’s too lazy, too vague, and too easy to deflect.

Think about it. “How was your day?” asks someone to summarize 16 hours of experience into one word. For a teenager whose brain is simultaneously processing social hierarchy, academic pressure, identity formation, and whatever drama unfolded in the group chat? That’s impossible. So they give you the only answer that’s safe: Fine.

The fix is smaller questions. Specific ones. Ones that don’t feel like an interrogation but do open a door.

Try these tonight:

“What was the most boring part of today?”

“Did anything make you laugh today — even a little?”

“If you could’ve skipped one thing today, what would it have been?”

“On a scale of 1 to 10, how was lunch?”

These work for a reason. They’re low-stakes. They’re specific enough to spark a real memory instead of a blanket summary. And they’re slightly unexpected, which breaks the autopilot response. And they don’t beg answers like, “yes / no” or “Fine”.

But here’s the part most people miss:

You have to go first.

Before you ask your kid about their day, tell them about yours. Not a highlight reel. A real moment. “The most boring part of my day was a meeting that could’ve been an email.” “I laughed today because I saw a dog wearing a backpack.”

When you go first, you’re not interrogating. You’re inviting. You’re showing them what safe vulnerability looks like. And over time — not overnight, but over time — that invitation gets accepted.

The dinner table is the best place on earth to practice this. Not because there’s anything magical about the furniture. But because it’s the one place where everyone is sitting still, without somewhere else to be, for at least a few minutes.

That’s your window. Don’t waste it on “how was your day.”

Use a better question. And watch what happens.

Every family eats, not every family is “Fine”.

— Chaps

P.S. Save this email. Try one of those questions tonight. Then share this newsletter with another family who may not be so “Fine.”