Jesus & the Sinful Woman

The story told in Luke 7:36-50 is meant to arrest your heart. Luke invites us to gaze into this portrait of the heart of God—seen in Jesus’ treatment of this woman—and be transformed by the encounter.

It begins with an invitation from Simon the Pharisee. The Pharisees were a powerful presence in the community, known as the religious and moral preservers of purity. We don’t know exactly why Simon invited Jesus, but we do know he was discourteous: he didn’t anoint Jesus’ head, greet Him with a kiss, or wash His feet. It was his way of saying, “You are not an authority over me.”

Then, a “woman of the night” enters. At important dinners like this one, the doors would be left open so others could come and listen in on the discussion. Her presence wasn’t surprising, but her identity was. She was a known sinner. We don’t know her specific story, but her reputation spoke for itself. The room was filled with stares that reminded her of her shame. Yet, somehow, she had heard Jesus’ message: love, grace, and forgiveness.

She summoned her courage, brought her bottle of perfume, and walked straight to Jesus. She didn’t speak, but her actions said everything. She stood near Him—close enough to see the mouth that spoke grace, the eyes that didn’t condemn, the hands that healed the broken. Her tears began to fall on His feet. She let down her hair—a scandalous act in that culture, reserved as a gift from a bride to her groom. In 1 Corinthians, Paul calls a woman’s hair her crown of glory. This woman unbound her crown and used it as a rag to wipe His feet. Then she kissed His feet and poured out her perfume. She is a living picture of Romans 6:13—offering every part of herself, once used for sin, in worship to the Savior.

Simon watched all this unfold and silently judged both her and Jesus. He thought, If Jesus were really a prophet, He’d know what kind of woman this is and wouldn’t let her touch Him. The irony? Simon only thought those words, but Jesus responded out loud, demonstrating the prophetic insight Simon had just denied.

Jesus then tells Simon a parable: two men owed a debt, one ten times more than the other. Neither could pay. Both were forgiven. Jesus asks, “Which one will love the moneylender more?” Simon answers—reluctantly—that it would be the one who had the greater debt canceled.

At that point, Jesus draws the contrast. He recounts all the basic courtesies Simon failed to offer and shows how the woman surpassed each one. Then Jesus says, in effect, Yes, Simon, I see this woman—and you should be learning from her. Simon’s love is cold because he doesn’t think he needs much grace. The woman’s love is extravagant because she knows how deeply she’s been forgiven. She recognizes the weight of her sin—and the worth of her Savior.

Jesus declares her sins forgiven. She wasn’t forgiven because of her love—that would contradict the gospel. Remember the parable: They couldn’t pay. Her love was not the cause but the result. Love received becomes love extended. Worship is our response to who He is and what He’s done. We’re not earning anything.

Why does Jesus call out her many sins? To show He’s not naïve. He knows everything—and still forgives. He also wants them to see that her sins were real. We’ve all missed the mark. We can’t fix ourselves. But we are transformed by the gospel. The union of our desperation and His redemption produces affection. Radical grace leads to radical generosity.

And Jesus isn’t saying you should sin more so you can enjoy more grace. You don’t need a messier past—you need a clearer view of your Savior. But don’t minimize your sin, either. You’ve been proud, selfish, dishonest. You need to see the heights of God’s holiness to understand how far you’ve fallen. Simon’s problem wasn’t a lack of guilt—it was a lack of awareness. He didn’t think he was that bad. His arrogance was just as offensive as the woman’s scandal.

We also tend to minimize Jesus’ forgiveness. Don’t believe for a moment that you can earn what Jesus has done. Don’t dishonor the Cross by thinking it’s Jesus plus your effort that makes you right with God.

So, how can Jesus offer this kind of forgiveness? Look again at the parable. The moneylender forgave the debt. In Scripture, debt is often equated with sin. Only God can truly forgive sin. And if God forgives sin, then we love God. Jesus connects the dots—she is worshiping Him because He is God. He has the right to forgive because He is the one who was offended. And the debt? It didn’t just disappear. It was paid. Jesus can say, “Your sins are forgiven,” because He is the payment for our sins.