The Parable That Found Us Sleeping

First Impressions Run Deep

I had the chance recently to teach through some of Jesus' parables of judgment. And something struck me in the process: how deeply a first reading of a story can root itself in our imagination. Once it’s there, it’s really hard to shake. Even when new interpretations make sense—even when the story itself invites us to see more—we often cling to that original impression. Maybe it's how we first read it. Maybe it’s how someone first taught it to us.

But that, I think, is the real genius of a parable. Jesus chooses a genre—in Hebrew, a michall—that’s meant to provoke, to push, to draw us into the work of interpretation. He could have just told us what to think. Instead, he offers a story with angles. A story that requires effort. Wrestling. Even disagreement. Because, in the Jewish tradition, truth isn't something you receive—it's something you strive for, together. And that shared struggle? That’s what shapes us.

Reading Parables with Imagination

This is what makes the parables so enduring. Not that anything goes—not every interpretation holds water. If it’s out of step with the ethic of Jesus, then it’s out of bounds. But inside that boundary, there’s space. Space to imagine. To ask new questions. To see new layers.

So that’s what I’ve been trying to do: say, hey, maybe what you heard isn’t the only way to hear this. Maybe there’s something under the surface, something slightly askew, that can enliven our imagination and our understanding of God. Something that wakes us up.

What If We All Fall Asleep?

Take the story of the ten bridesmaids. You know it: ten waiting, five prepared, five not. The groom is delayed, and when he finally shows up, only half make it into the party. The other half are locked outside.

The traditional read? Be prepared. Stay vigilant. Be ready, because Jesus could come back at any moment. And if you’re not? Well, you’re out. It’s over.

But the more I sit with this story, the more I wonder if that interpretation has missed the point entirely. Because look again: all ten fall asleep. Every one of them. Their lamps go out. No one is ready when the groom finally arrives.

That’s not a story about who stayed watchful. It’s a story about everyone missing it. Everyone failing. Everyone falling asleep.

The Wrong Question

Back in chapter 24, the disciples ask Jesus: how will we know the sign of your coming? And initially, it seems like his answer is: you won’t. But maybe that’s only half of it. Maybe what Jesus is really saying is: you won’t, and that’s okay. Because you’re all going to fall asleep anyway.

Maybe this story isn’t about those who got it right. Maybe it’s about those who know they’re going to get it wrong. Who know they won’t see it coming. Who stop trying to earn their invitation through vigilance or readiness or perfection.

Because, in the end, no one gets into the party by the sweat of their brow. Or by their spotless character. Or even their disciplined watchfulness. That’s not how Jesus’ parties work.

The Invitation Was Never Earned

Jesus throws parties for the ones who fall asleep. For the ones whose lamps go out. For the ones who deny him, betray him, doubt him. If you start thinking it’s about having enough oil, or tracking your wins and losses, then maybe you’ve missed it.

Because your invitation never depended on your ability to read the signs. It was only ever about trusting that he would come. That he would wake you up when the time was right.

When we make peace with our limitations—when we accept that we’re going to fall asleep, that we’re going to miss it—we start to understand something profound. That the party was always about grace. And the only way to miss it is to think you can earn your way in.

Caught Off Guard by Grace

Jesus isn’t telling this story to judge his disciples for not being ready. He’s saying: you can’t be ready. You’re going to fall asleep. You’re going to be surprised.

But Grace? Grace is still coming for you.

The real judgment here isn’t about failure. It’s about the illusion that readiness could ever be what earns your place. The story is calling us to stop trying to do just enough—and instead to live as though we are absolutely convinced the party is coming.

Eventually.

And that when it does, grace will be enough to wake us up.