Here's something I've learned about family dinner conversations:

Questions are good.

But challenges are better.

There's a difference between asking your kid "How was your day?" (which gets you a "Fine" at best) and saying:

"If you were stuck on a deserted island, how would you escape?"

One is a question. The other is a challenge.

Challenges engage a different part of the brain. They spark creativity. They invite problem-solving. They're actually fun.

And here's the magic: when kids are solving a hypothetical problem, they often start sharing real things about themselves. Often without even realizing it. You can get to know quite a bit about another in how they answer questions, or solve problems.

The way they approach the deserted island escape tells you something about how they think. What they value. What scares them. What excites them.

You learn more from a silly challenge than from a hundred "How was school?" questions.

This is why I'm a big believer in dinner challenges.

Not interrogations. Not lectures. Challenges.

"If you could start any business with $100, what would it be?"

"If you had to survive one week with no phone, what would you do?" (*CAUTION: This question might cause them to be skeptical or think you might be planning to take their phones away - use carefully.)

"If you could add one rule to our family, what would it be?"

Age-appropriate, of course. But even young kids can handle a good challenge.

And here's the best part: everyone participates.

It's not a parent grilling a child. It's the whole family playing together. Parents have to answer too. The playing field is level.

That's when real connection happens.

Challenges stimulate thinking.
Thinking creates conversation.
Conversation builds connection.
Connection builds family.

That's the chain.

Tonight, try this:

"Here's $1,000 and one week. You have to plan a family adventure. Where do we go and what do we do?"

Let everyone weigh in. Argue about it. Dream together.

That's dinner done right.

— Chaps

P.S. What's the best dinner table challenge or game your family has ever played? I'm always looking for new ideas. Hit reply.

P.P.S. If you know a family that could benefit from this, please encourage them to subscribe to Dinnercommander.com. Let’s make families stronger together!

Every family eats, not every family plays together.