How Often I Would Have Gathered You

Matthew 23:37-39 - “O Jerusalem, Jerusalem, the city that kills the prophets and stones those who are sent to it! How often would I have gathered your children together as a hen gathers her brood under her wings, and you were not willing! See, your house is left to you desolate. For I tell you, you will not see me again, until you say, ‘Blessed is he who comes in the name of the Lord.’”

There’s someone in your life who keeps refusing what they need most.

You’ve watched it happen slowly. The conversation they won’t have. The help they won’t accept. The invitation they keep declining. And at some point, your concern quietly hardened into frustration. You stopped feeling sad about it and started feeling annoyed. You stopped praying with tenderness and started praying with an edge. Maybe you stopped praying about it altogether.

We know what it’s like to love someone who won’t be reached. And we know how quickly that love can curdle into something colder.

Matthew 23 is the longest, most blistering rebuke Jesus ever delivers. Seven woes. Five accusations of blindness. He calls the Pharisees whitewashed tombs, blind guides, children of the men who murdered prophets. It’s one of the most intense confrontations in Scripture.

And then the tone shatters.

“O Jerusalem, Jerusalem… How often would I have gathered your children together as a hen gathers her brood under her wings, and you were not willing.”

After everything He just said, this is what comes next. Not a final condemnation. A lament. The voice that thundered seven woes now breaks with grief. Jesus wanted to gather them. He longed to draw them close. Over and over. How often, He says. This wasn’t a one-time offer they missed. It was a repeated, aching pursuit they kept refusing.

The image He chooses is worth sitting with. A hen gathering her brood. In a fire, a hen will spread her wings over her chicks and burn alive rather than leave them exposed. She doesn’t fly away. She absorbs the heat. She dies so they can live.

Jesus chose that image for Himself. On purpose. Because in a few days, He would spread His arms on a cross and absorb the full weight of the wrath these very leaders deserved. The One pronouncing the woes would become the One bearing them.

And the devastating phrase: “you were not willing.” Not unable. Unwilling. They had every chance. Every prophet. Every invitation. Every moment of Jesus standing in their temple, looking them in the eye. And they said no. Repeatedly.

We hear that and our instinct is to judge them. But there’s something else here for us. Something about how Jesus holds both truth and grief at the same time. He doesn’t soften the rebuke to protect His tenderness. He doesn’t abandon His tenderness to sharpen the rebuke. He holds both. Full honesty about their condition. Full ache over their refusal.

We’re not very good at that. When someone we love keeps refusing what they need, we tend to pick one or the other. We go soft and stop telling the truth. Or we go hard and stop feeling the grief. Jesus does neither. He weeps over the very people He’s just confronted.

What would it look like to hold that kind of tension for the person in your life who keeps saying no? To stay honest about where they are and still ache for them the way Jesus aches for Jerusalem?

The gospel gives us the capacity. Because we were Jerusalem once. We were the ones who kept refusing. And Jesus didn’t give up. He spread His wings and absorbed what we deserved. That’s the mercy that makes us capable of tenderness toward people who don’t want our help.

Application: Pray for the person in your life who keeps refusing what they need. Pray with tenderness, not frustration. Ask God to give you His grief for them instead of your annoyance.

Prayer: “Jesus, You wept over the people who rejected You. I confess I’ve grown frustrated with the people who keep refusing help. Replace my annoyance with Your ache. Help me love them the way You loved Jerusalem. Amen.”

-PK