Woe is Me: Blessing in the Woes

Aug 31, 2026

Devotional

Day 1: The Hen’s Wings and Our Resistance

Jesus’ lament over Jerusalem reveals a love that persists even when met with rejection. His image of a hen gathering chicks under her wings contrasts sharply with humanity’s tendency to flee from divine shelter. The religious leaders’ history of killing prophets mirrors our own patterns of resisting God’s voice—through pride, distraction, or willful disobedience. Yet Jesus’ question “How often would I have gathered you?” echoes beyond ancient Israel to every heart that avoids His refuge. His longing outlasts our rebellion. The door remains cracked for those who’ve preferred wilderness to His wings. [38:42]

“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!”
(Matthew 23:37, ESV)

Reflection: Where have you most resisted Jesus’ gathering love this week—in your schedule, relationships, or secret struggles? What makes it hard to let His shelter feel safer than your independence?

Day 2: Desolate Houses and the Harvest of Hardness

A temple left desolate becomes a warning: what we cultivate in our hearts inevitably shapes our spiritual home. The religious leaders’ hypocrisy created a hollow religion, just as unconfessed sin drains vitality from our walk with Christ. Jesus’ words about reaping what we sow apply to both societies and souls. When we prioritize image over integrity or comfort over conviction, we risk exchanging God’s presence for empty rituals. Yet even in desolation, the promise remains—He still knocks. [01:00:48]

“Do not be deceived: God is not mocked, for whatever one sows, that will he also reap. For the one who sows to his own flesh will from the flesh reap corruption, but the one who sows to the Spirit will from the Spirit reap eternal life.”
(Galatians 6:7-8, ESV)

Reflection: What “crop” is growing in the soil of your daily choices—bitterness or grace, self-reliance or dependence? Which area of life needs uprooting to avoid spiritual famine?

Day 3: Sparrows and the Apple of God’s Eye

Jesus’ tender metaphor of protective wings meets its counterpoint in Psalm 17’s plea to be “the apple of God’s eye.” Even as He rebukes hypocrisy, Christ affirms the rebels’ infinite worth. The same hands that cleared the temple with a whip now ache to shield those who oppose Him. This paradox defines the gospel: we matter enough to be corrected, loved enough to be pursued through our worst resistance. His longing isn’t diminished by our wandering. [55:13]

“Keep me as the apple of your eye; hide me in the shadow of your wings.”
(Psalm 17:8, ESV)

Reflection: When have you assumed God’s disappointment instead of His delight? How might embracing your status as “the apple of His eye” change today’s struggles?

Day 4: Woe Is Me: The Door Still Open

After seven woes, Jesus leaves a startling invitation. The prerequisite for seeing Him—“Blessed is He who comes in the Lord’s name”—isn’t a threat but a lifeline. Like the father in the prodigal parable, He waits for the slightest turn toward home. The religious leaders’ story wasn’t over, nor is ours. Every “woe is me” moment—over self-sufficiency, hidden sin, or pride—becomes a threshold back to grace. [01:18:54]

“He sent his son to them, saying, ‘They will respect my son.’ But when the tenants saw the son, they said to themselves, ‘This is the heir. Come, let us kill him and have his inheritance.’”
(Matthew 21:37-38, ESV)

Reflection: Which “woe is me” applies today—needing Jesus but acting self-sufficient, staying in desolation, or relying on self-righteousness? What first step would honor His open door?

Day 5: Crushed Grapes and the Cup of Longing

Communion’s bread and cup memorialize the cost of Jesus’ persistent love. The Son killed by tenants now offers His body and blood to reconcile those tenants. This meal isn’t for the perfected but the penitent—those who bring their weariness, failure, and lingering resistance to the table. The same hands that longed to gather Jerusalem now extend grace’s elements, proving no wretchedness outweighs His desire to redeem. [01:23:20]

“But God shows his love for us in that while we were still sinners, Christ died for us.”
(Romans 5:8, ESV)

Reflection: What part of your story feels too broken to bring to Communion? How does Jesus’ death for enemies (you then, others now) reshape that narrative today?

Sermon Summary

Jesus closes Matthew 23 not with one more blow against the religious leaders, but with a heart-breaking invitation. The chapter has been heavy. Jesus has called out hypocrisy, blind religion, burdens laid on people’s backs, and a whole system that looked holy on the outside while resisting God on the inside. Yet Jesus does not let anybody sit back and say, “Look at how messed up they were.” The text presses the question closer: where does a heart need to say, “Woe is me”?

Jesus names Jerusalem as the city that kills prophets and stones those sent to her. Israel’s history shows a long pattern of resisting God’s love. The vineyard parable shows servants beaten, killed, and stoned, until finally the Son himself is sent. Zechariah’s death at the command of King Joash shows how far rebellion can go, even in the courts of God’s house. Jesus stands before leaders who will soon reject and murder the Son of God, and still he says, “How often would I have gathered your children together.”

Jesus uses the image of a hen gathering her brood under her wings. That picture carries refuge, protection, care, provision, and nearness. God’s steadfast love has never ceased, even when his people have repeatedly turned away. Christ died for sinners while they were still sinners, enemies, and rebels. Jesus does not wait for the woefully wretched to clean up their act before he longs for them.

Jesus also declares that Jerusalem has reaped what she sowed. “Your house is left to you desolate” signals that the temple, corrupted into a den of robbers, is being left to the consequences of its rebellion. Romans 1 and Galatians 6 show the same frightening pattern: God gives people over to stubborn hearts, dishonorable passions, and debased minds when they persistently suppress the truth. Hypocrisy may fool people, but God is not mocked.

Jesus leaves the door open through a required response: “Blessed is he who comes in the name of the Lord.” The wretched remain woeful unless they humble themselves, turn from hardness, and receive Christ as the promised King. Communion then becomes a table not for super great Christians, but for repentant Christians resting in the finished work and goodness of Jesus.

Key Takeaways

1. Jesus longs for rebellious hearts Jesus does not look at rebellion with indifference. His grief over Jerusalem reveals a real longing to gather, protect, and receive people who have resisted him. Christ’s invitation reaches even into hearts that have grown hard through long patterns of sin. [52:44]
2. God’s love meets sinners before change Christ died not for cleaned-up people, but for enemies who were still running their own lives. The cross exposes sin for what it is while also displaying love deeper than human rebellion. Grace does not minimize wretchedness; grace meets it with the sacrifice of Jesus. [57:37]
3. Sin always reaps a harvest Persistent sowing to the flesh does not stay contained or harmless. God’s judgment can include giving stubborn hearts over to the very desires they have chosen. Hidden hypocrisy eventually stands exposed before the God who cannot be mocked. [65:18]
4. Hope requires a different response Jesus offers more than condemnation, but his invitation calls for humility. Hardness must give way to confession, self-rule must give way to Christ’s kingship, and self-righteousness must give way to trust. “Blessed is he who comes” becomes the cry of a heart that has stopped resisting. [75:18]
5. Communion belongs to repentant Christians The Lord’s Table is not a reward for having a good week. The bread and cup remind struggling believers that refuge rests in Christ’s broken body and poured-out blood. Repentance brings needy hearts back under the shadow of his wings.

## [83:20]

Youtube Chapters

[00:00] - Welcome
[37:26] - Matthew 23 and the Woes
[41:08] - Jesus Wants the Woefully Wretched
[42:42] - Resisting God’s Love
[43:50] - The Vineyard and the Rejected Son
[49:45] - Gathered Under His Wings
[57:13] - Love for Enemies
[60:10] - Reaping What Has Been Sown
[65:18] - God Gives Them Over
[73:14] - Rejoice in Hope or Reject in Hardness
[78:54] - Three Woe Is Me Questions
[82:25] - Communion and Christ’s Finished Work
[92:40] - Trusting the Goodness of Jesus

Bible Study Guide

Bible Reading

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.’”
[38:42]

Romans 5:8
“but God shows his love for us in that while we were still sinners, Christ died for us.”
[57:26]

Galatians 6:7–8
“Do not be deceived: God is not mocked, for whatever one sows, that will he also reap. For the one who sows to his own flesh will from the flesh reap corruption, but the one who sows to the Spirit will from the Spirit reap eternal life.”
[01:07:25]

Romans 1:24, 26, 28
“Therefore God gave them up in the lusts of their hearts to impurity, to the dishonoring of their bodies among themselves... For this reason God gave them up to dishonorable passions... And since they did not see fit to acknowledge God, God gave them up to a debased mind to do what ought not to be done.”
[01:05:18]

Observation questions

What words in Matthew 23:37 show both Jerusalem’s long history of resistance and Jesus’ continued desire to gather her people?
What does the picture of a hen gathering her brood under her wings communicate about the kind of refuge Jesus offers? [54:16]
In Matthew 23:38, what change is heard in Jesus’ words when he calls the temple “your house,” and what does “desolate” mean in this context? [01:00:34]
What repeated phrase appears in Romans 1:24, 26, and 28, and what does it reveal about the consequences of persistently rejecting God? [01:05:18]

Interpretation questions

Jesus grieves over people who reject him and yet says, “How often would I have gathered you.” How does this keep God’s judgment and God’s compassion together rather than putting them against each other? [49:45]
Romans 5:8 says Christ died for people while they were still sinners. Why is it important that grace does not begin after a person has cleaned up his or her life? [57:40]
Galatians 6:7–8 warns that people reap what they sow. What might it look like for a person’s heart to become harder through repeated choices to sow to the flesh? [01:08:59]
“Blessed is he who comes in the name of the Lord” is more than words of religious respect; it is a humble welcome of Jesus as King. What kind of heart-change is required for someone who has been resisting Christ to say this sincerely? [01:17:06]

Application questions

It is easy to see hypocrisy and hardness in others while missing it in ourselves. Where have you known what obedience to Jesus looks like but resisted it recently—through pride, anger, bitterness, laziness, lust, greed, or something else? [48:20]
Jesus does not wait for rebellious people to become impressive before he calls them near. Is there a sin, failure, or ongoing struggle that has made you feel like you should stay away from him? What would it look like to come honestly to him instead? [59:16]
God is not mocked, even when people can maintain a convincing outward appearance. Are there places where you are tempted to wear a spiritual mask, hoping others will think better of you than is true? What could honest repentance look like in that area? [01:09:31]
Sowing to the flesh and sowing to the Spirit show up in ordinary choices. Looking at your use of time this week, what is one concrete way you could make more room to seek God in his Word and prayer? [01:10:42]
Consider your relationships with people who do not know Jesus. Do your conversations and choices show only a desire for comfort and fitting in, or is there room for gospel intentionality? What is one person you could pray for and pursue with love this week? [01:12:05]
Jesus’ invitation calls for a response: humility, repentance, and trust in him rather than trust in self. Which is the greater temptation for you right now: acting like you do not need Jesus, staying stuck in guilt and desolation, or resting in self-righteousness? [01:18:54]
Communion is not a reward for Christians who have had a good week; it is a reminder of Christ’s finished work for repentant Christians. How does this truth change the way you come to Christ after a week of struggle or failure? [01:23:20]

Sermon Clips

51s

#LovedWhileEnemy

“Realize what this does not say. This does not say that God shows his love for us, that when we finally cleaned up our act and and started being so stupid that that Christ died for us? This does not say that that God showed his love for you when you stopped doing so many sinful, rebellious things that Christ died for you. Listen very carefully. When you were an an enemy of God, when you were in absolute opposition, when you were walking following self as king, not Jesus as king, God loved you so much that Jesus died to pay the price for all of your enmity, for all of your rebellion, for all of your sin.”

45s

#ComeToHisWings

“Let me let me speak to you today. Let me let me act like we're in my office, just you and I, and I ask you that question. What do you think God would say to you right now? What would your response be? Would you give the response? He disappointed in me. He's tired of me. He's angry at me. Or would you understand that he would say something like, I long for you? That he would say to you, come. Come in my refuge. Come be hidden under the shadow of my wing. Come.”

29s

#RepentantNotPerfect

“This is not a moment for super great Christians. This is a moment for repentant Christians. This is not a moment that you you earn because you've had a good week. This is a moment that you are reminded of the goodness of Jesus. So I encourage you to take this moment to posture your heart toward continued repentance as we remember who Jesus is and what he's done.”

53s

#TurnToJesusPath

“This summer, we've seen the wretchedness of the first century Jewish leaders. And if we've been willing, we've seen, let's be honest, we've seen the wretchedness that can be found in our own hearts. And Jesus wants Instead of driving the final nail home, we actually see that Jesus cracks the door and says, I have a different path if you're willing to turn from your wretchedness. That's what we're going to discover today in this incredible passage. At the end of the seven woes, Jesus still longs to see these religious leaders turn to him. And Jesus today, he longs to see you turn to him.”

39s

#JesusLongsForYou

“That's why I think this passage is a passage of hope. Because we have a room full of people that you've just thought about your history over the past week. And and if you're willing to let your guard down, there's been places where you have been woefully wretched. May maybe no one has seen it. No one else knows. But you've been woefully wretched. And we expect the the shoe to drop. We accept expect the judgment to come. And yet, what what do you find? Is Jesus' posture toward you right now? He longs for you.”

52s

#YourStoryIsntOver

“Two thousand years ago, as they stood before Jesus, their story was not over. And listen very carefully, church. Your story right now is not over. Maybe as we've talked about being woefully wretched, we've been talking about you. Maybe you become an expert at putting the veneer on. Maybe you can play church with the best of them. Maybe you've been self deceived. But listen very carefully. Not only is God not mocked, but listen, Jesus still longs for you.”

34s

#RunToJesusNow

“Woe is me first if instead of running to Jesus, I act like I don't need him. That that was their issue with the religious leaders. They didn't they didn't need him. Is that you? Are you just holding life together the best you can, or are you running to Jesus and his grace and his mercy? Number two, woe is me if instead of returning to Jesus, I remain in my desolation.”

42s

#JesusWantsTheWretched

“And as we come to the end of chapter 23, we can almost anticipate the final nail being sunk into the coffin. We can almost anticipate even greater condemnation brought to them. But that's not what we find. Today's text, I want to show you something marvelous. I want to help you see a truth in this passage that is unexpected, that is surprising, and that it is beautiful. And here's the truth. The truth is this, that Jesus wants the woefully wretched.”

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