Rev. Nick Cheek
Matthew 5: 1-10
Intro: This morning we are continuing our sermon series on the Beatitudes. As a little refresher, the beatitudes (talk about Jesus’ first teaching really… so we should pay attention to them. Through these Beatitudes, Jesus is presents us with a different “attitude”… he paints a contrary portrait of a blessed life by turning the world’s view upside down. The beatitudes are a refocusing – not on who or what the world considers blessed… but on who and what God considered blessed. The beatitudes are not about what we can do to better ourselves, they are about what we can do to live into the Kingdom of Heaven. As so, through his first teaching, Jesus shines a magnifying glass on the heavenly attitudes that are often disregarded by the world. And as we look closely at these beatitudes each week… we will find is that they are painting a portrait of Jesus Christ himself. A portrait of who he was… what he cared about and how he lived his life.
Today’s beatitude is Blessed are the poor in spirit for theirs is the Kingdom of Heaven. This particular Beatitude turns our attention to the idea of spiritual poverty. Blessed are those who are spiritually poor… whose spirits are week and in need… blessed are those who desperately need the grace of Jesus Christ.
In our second reading this morning we encounter a women who is most certainly in need of this beatitude. Our story takes place in the house of Simon, a Pharisee – a member of the religious elite. While everyone is partying and having a good time, in walks a woman who abruptly falls at the feet of Jesus.
Scripture and Prayer
Imagine the setting. Simon has opened his home — the table is spread, the wine is poured, the lamps are lit. Guests recline on cushions around the low table, talking, laughing, dipping bread into bowls of oil. The room feels alive with conversation — a gathering of respected people, religious leaders, curious neighbors, maybe even a few who had been following Jesus from a distance. It is the kind of dinner where reputations matter, where every word and gesture is noticed.
Into this carefully arranged scene — the food, the drink, the company, the social expectations — walks a woman who doesn’t belong. She has no invitation, no standing, no reputation worth protecting. She moves past the murmurs, past the startled looks, and heads straight for Jesus. And then, in front of everyone, she kneels down and begins to weep.
The crowd in Simon’s home thought her behavior to be scandalous. How dare this woman walk in uninvited, unannounced — and then, in full view of everyone, kneel at Jesus’ feet? How dare she wash them with her tears, dry them with her hair, and kiss them with abandon? Their eyes narrowed. Their spirits stiffened. They may have even murmured to themselves, “sinner”.
Simon was convinced that if Jesus really knew what kind of woman she was, he would never let her touch him. And maybe the whole town agreed. Galilee was a small place—the kind of place where everybody knows your name, and everybody thinks they know your story, too.
If you’ve ever lived in a small town, you know how wonderfully gracious they can be… but at the same time, we also know how hard it can be to find acceptance in a place that rarely forgets your mistakes. A place that can trap you inside the worst chapter of your story, even when you’ve been trying to write a new one.
Galilee had already made up its mind about this woman. But we don’t have to. Because the truth is—we don’t know her story. Her true story could be anything. It might sound like your story. It might include waves that have been crashing over her for years. Wounds that keep reopening. Wounds that never seem to heal.
Her story might hold seasons of addiction or despair. It might carry depression, rejection, or loneliness. Maybe she endured broken relationships, or the loss of a job, or the loss of someone she loved. Maybe she even lost herself somewhere along the way.
We don’t know the details. What we do know is this: her behavior shows us she is in desperate need. The original language says she rained tears at Jesus’ feet…. She bathed them with her tears. Watched them with her hair.
Blessed the poor in spirit… for theirs is the kingdom of Heaven
I wonder what Simon was thinking as this scene unfolded. Did his heart soften toward conviction, or did it remain hardened in pride? Perhaps he told himself, “My spirit is fine just as it is. I don’t need what she needs. Jesus, I can honor you with a seat at my table, with a glass of wine, with polite conversation. But this? This falling at your feet? This extravagant display? This awkward devotion? No thank you.”
I understand Simon’s discomfort. I struggle with this woman’s posture too. It is far easier to serve God in ways that keep me standing tall—attending worship, joining a study, traveling on a mission trip, debating theology. But to fall at Jesus’ feet? To confess a deep and aching spiritual poverty? That is harder… It’s also risky.
If we are honest, this scene is uncomfortable. To witness such raw, unhindered expression unsettles us. Imagine if someone were to walk into our sanctuary this very moment—making their way down the aisle, falling to their knees at the front, tears streaming, hands clasped, heart pouring out in unrestrained vulnerability. How would we respond? What would we feel? What would we do?
Perhaps, like Simon and his guests, our first impulse would be judgment. This is not the time. This is not the place. Someone should intervene. This is too much, too disruptive, too improper.
We might prefer order, dignity, or restraint. We might ask that her tears be scheduled. Can’t she… fill out a card? Take a number… deal with whatever this is… later. This is not the time or the place for a display of emotions?
And yet… another impulse might stir within us. Perhaps her vulnerability would awaken in us… something that may have long been hidden or suppressed. Perhaps we would feel not embarrassment, but longing.
Watching her tears, we might whisper in our own hearts: I need that too. I need to let go. I need to be honest about, my longings, my brokenness, my wounds, my deep need for God. Lord, fill my poor spirit up, with your grace and mercy… and love.
By letting down her hair, touching Jesus, and pouring out her tears, she crossed every social and religious boundary of her time. She risked rejection, social disgrace, possibly even being driven from the room. But she risked all of that because her need was greater than her fear. She chose real honesty instead of hiding… she risked much on the promise of one hope—that at the feet of Jesus, she might find mercy.
Blessed are the poor in spirit, for theirs is the Kingdom of God.
Barbara Brown Taylor reframes “poor in spirit” as the moment we let go of the exhausting performance of self-sufficiency. In a culture that prizes strength, appearance, and spiritual achievement, Jesus declares blessedness for those who finally admit they are empty, needy, and unable to carry the load alone. To be poor in spirit is not about cultivating weakness but about becoming honest before God.
Taylor suggests that the blessed ones are those who stop faking it — those who are tired of hiding their brokenness behind masks of competence or control. These are the people who stumble into the blessing of grace, not because they earned it, but because in their vulnerability, they are finally open to receiving it.
Barbara Brown Taylor writes in Gospel Medicine:
“The poor in spirit are those who have finally run out of self-confidence, those who have lost their grip, those who are so tired of pretending to be strong that they are ready to be honest. Blessed are you when you are at the end of your rope and the mask slips. Blessed are you when you have nothing left to prove and no one left to impress. For it is precisely there, in that emptiness, that God meets you with fullness.”
I’ve been thinking about Simon all week. Where is he really in this story? The focus seems to be on the woman, rightfully. But Simon is not in the background. As Jesus’ grace is extended to the woman at his feet, he also calls Simon by name… “Simon… watch… listen… look upon this woman.” And as she continues to wash Jesus’ feet, bathing them with her tears and anointing them with oil, I have to wonder if Simon’s heart began to beat faster.
As his eyes glanced to the other guest… first out of embarrassment…maybe those same eyes looked upon the woman with envy. Perhaps Simon longed for the courage to act as she did. Perhaps he envied her freedom to let go of appearances, let go of proper protocol or social norms… and pour herself out at Jesus’ feet. Maybe he even wished he could love with that kind of abandon. Maybe he wished too, that he could have the permission… to fall down in utter need… the permission to ask for help… to ask for healing… the permission to let go of all he was carrying and just lie at the feet of Jesus.
I don’t think Jesus names the contrast between Simon and the woman in order to shame Simon. I think he does so, to invite him. Jesus wants Simon to see that the very grace the woman receives is no less available to him. If only he could see it, if only he could risk stepping down, Simon too could discover that the Kingdom belongs to this woman… it belongs to him… and it belongs to us.
Rachel Held Evens reminds us that “To kneel before Jesus isn’t to enter judgment—it’s to enter bold, untamable grace.”
Where are you today, church?
Do you need permission to sit at the feet of Jesus?
Some of us out here may be tired of holding it all together — faking it until we make it. Some of us out here today may be weary from carrying heavy burdens… pretending to have unending strength. Some of us out here today may be exhausted from trying to stay positive when life feels excruciatingly uncertain and even scary at times. Some of us out here today are wrestling with forgiveness — struggling to forgive ourselves, or finding it hard to forgive others.
And here is what Jesus says to you this morning:
You are blessed…
Blessed when you let go.
Blessed when you admit your faults and failures…
Blessed when you realize you don’t have to carry it alone.
Blessed when you take my yoke upon you, for my yoke is easy and my burden is light.
Blessed when you surrender your burdens…
Blessed when you sit at my feet.