Jesus and the sinful woman

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meals with Jesus in Luke

Imagine you are at a respectable dinner party – at the local major’s house. The dinner is on honour of a visiting speaker. Of course you are excited, because you’ve heard about the speaker and are intrigued about his views. During the meal suddenly the doorbell rings and you think nothing of it until a woman pushes her way into the room. The major’s wife’s face is a picture. The new arrival is wearing a tight fitting low cut blouse, a short skirt, or is it a belt and stiletto heels. She’s got gaudy make up and totters as she walks in. She looks like a prostitute. She goes straight up to the visiting speaker and throws her arms around him, pulling his head to her chest. “I’ll always be yours”. She mutters. She begins to massage his shoulders – then you notice she is crying, mascara streaking down her cheeks.
Everyone freezes. How embarrassing. But instead of pushing her away he re reaches up puts an arm around her and says something that sounds like “And you’re mine” – surely he cant have said that. She might think it is a come one. Maybe it is, maybe he is a customer.

That’s a modern version of today’s meal with Jesus – in Luke 7:36-50

Amazing picture painted. What do you do when you see a painting? Do you stand back and gaze at the whole thing or do you focus right in?
Reminds me off that amazing scene in “Ferris Beullers Day off” – one of the best films of my teenage years – were Ferris, Cameron and Sloane are in the institute of art in Chicago and Cameron starts staring at a Seurat. The camera keeps cutting between Camerons eye’s and the Seurat zooming in each time closer and closer till you see the individual points but miss the whole.

Setting the scene
Do we look at the broad stokes or focus in, or both?!
Tom Wright writes of Luke 7 like this “Consider first the overall effect…. three characters dominate the stage: Simon the Pharisee, Jesus and the unnamed woman. The balance of the scene is superb, with Jesus keeping his pose between the outrageous adoration of the woman and the equally outrageous rudeness of his host and yet coming up with some thing fresh, something which, to the onlookers, was just as outrageous as the behaviour of the other two, The story sweeps to and fro between then with passion and power.”

Last week we saw how Levi, the tax collector – who should have been God’s go between had become Rome’s go-between, a traitor ripping people of to collect taxes. Jesus ambushes him with follow me, putting back on his prophetic destiny. Levi responds with a great feast mixing his non-Christian and Christian friends together. The Pharisees are there, hypocritically as it turns out as they criticise Jesus for being with sinners. Jesus’ response shows us that everyone needs to know God loves them, wanting to be with them and so we need to repent – to turn to God and join the party of the kingdom of God. We need to repent, whether we know we are sinful like the tax collectors or think we are already righteous like the Pharisees.

So one of the Pharisees is intrigued, Simon, invites Jesus to another feast. He wants to know more, to know whether Jesus really is The Prophet. Jesus goes, because who you eat with shows who you have solidarity with.
Houses were much more open then than ours, people could come and go and see what was happening especially at such a prestigious home. This no ordinary home – Pharisees guarded their purity closely. The Promised land had been defiled by Roman occupation, but at least devout Jews could keep their bodies pure.
They were reclining around a table – heads towards the table and feet towards the walls.

The sinful woman
Into this dinner party a sinful woman comes, bringing a jar of perfume. To the Pharisees this woman is like an infectious disease, yet Jesus is clearly accepting her. It’s a shocking display of intimacy.
She lets her hair down to wipe her tears from Jesus feet. In that culture letting your hair down was what you did in the bedroom. It would be like appearing topless now in public. She kisses his feet and pours perfume on them. Is he a client? But its the only way she knows how.
He doesn’t stop her. He could have said, “I appreciate what you are doing, but its not appropriate here” but he doesn’t. One scholar writes “Jesus’ passivity in the face of this behaviour is extremely eloquent.”

As Tim Chester writes prostitution is a commercial parody of hospitality. But Jesus recognises her actions as the real thing. He reinterprets what she does as a loving act rather than an erotic act.

Jesus response is amazing – his reputation is at stake. One of the religious leaders of the day, Simon the Pharisee is checking him out. He was wondering whether Jesus is a prophet. Now he knows he is not. “he says to himself “If this man was a prophet he would know who and what sort of woman this is who is touching him, that she is a sinner.”

Just before this story in Luke in v34 we find Jesus accused of being a glutton and a drunkard, an allusion to Deut 21:21 which describes how a rebellious drunken son must be stoned. They are saying Jesus is a rebellious son of Israel – but v35 let’s see what fruit comes from this. The irony is he does die the death of a rebellious son, hung on a cross not stoned. The irony is he does die the death of a rebellious son, hung on a cross not stoned. And of course the fruit is the resurrection!

Jesus is a friend of sinners and happy to associate with them. He’s a friend of the foreigners, the riff raff, the traitors, the unrespectable, the drunks, the prostitutes, the mentally ill, the broken and the needy.

Jesus’ response
He is a prophet – he knows what Simon is thinking, so in v40 he tells Simon he has something to say.
He tells a parable of two people in debt, having that debt cancelled. He hooks Simon in with a question – which one loves more?
Of course the one forgiven more.
Debt was personal – not a faceless credit card company. Incurring a debt was a personal debt, that couldn’t ever be fully repaid. A creditor could forgive it, but the one who was absolved would forever have a debt of gratitude.
Having drawn Simon in, Jesus then personalises it as him and the sinful woman.
Jesus describes what the lady had done

Etiquette of hospitality required that guest would have water to wash their feet as they came in from the dirty dusty roads. Today we may shake hands, take coats and offer a drink. In Jesus’ day it would be water for your feet and greeting with a kiss. Simon didn’t do that – he’s the host who isn’t a host. And the sinful woman is a host who’s not even a guest…

SO Jesus contrasts them
You gave me no water for my feet, but she has wet my feet with her tears and wiped them with her hair.
You gave me no kiss, but from the time she came, she has not ceased to kiss my feet
You did not anoint my head with oil, but she has anointed my feet with ointment.

His lack of welcome and her lavish welcome say a lot about love and forgiveness – v47

The Pharisee was forgiven little, so he loved little. Perhaps he had less to be forgiven of, more likely he had repented less.

Her love didn’t bring about the forgiveness, it flowed from it.

The challenge
Luke is writing to churches in around 80AD and to us, to challenge us with the words of Jesus. Do our attitudes and behaviour mirror Simon or the sinful woman?
Do we welcome and are we reconciled with everyone who has repented and been forgiven?

Part of last week’s meal was recognising that everyone needs to repent to enter the kingdom of God, this week we are faced with being reconciled to others who have come into the kingdom.
Luke will repeat it in ch15 where the Pharisees complain about Jesus welcoming sinners and eating with them. Then he responds with the parable of the lost coin, that is found, the lost sheep that is found and the lost younger brother that is found. The older brother refuses to welcome him back.

Simon the Pharisee hasn’t shown the normal courtesies of a host and despised this poor woman. He hasn’t shown love. The only conclusion can be that he’s been forgiven little – and probably not at all. He is a legalist. Meals express inclusion. But this meal has been warped by legalism. Simon wants to express the wrong kind of inclusion. He thinks he’s invited the righteous, so the unrighteous have to gatecrash. But Jesus shows us Simon has misunderstood righteousness.

Simon thought Jesus can’t be a prophet because he hadn’t seen this woman’s character. But Jesus is and had seen right inside – into her heart we she knows her sins are many and that she has received forgiveness.

Genuine repentance makes a difference it includes us in the kingdom. Simon clearly thinks once a sinner always a sinner – but the gospel transforms us!
Simon said to himself and then Jesus responds out loud. Simon’s heart attitude has been exposed. Difficult people have a habit of doing that!

Whenever we look down on someone for being smelly or disorganized or lazy or emotional or promiscuous or socially inept or bitter, then we are being like graceless Simon. When we look down on others for not understanding grace, we are being like Simon. If you think this applies to someone else you are being like Simon. Jesus says to us if you look down on others, you love little because you understand so little of your own sin and my grace.

Application
1) You know your life has been a mess, Jesus welcomes you now. Forgiveness, acceptance – turn towards him and receive it
2) Look down on others, stop being like Simon. Repent and be forgiven much
3) Be welcoming! Most welcoming church in the area – not hard. Can with God’s grace, be better!
Sundays, invite to life groups, most welcomed when you eat with others – even simple food. Around a table everyone is a friend and if not it’s immediately obvious and an opportunity to deal with it!

Unsanctified Compassion

When our compassion is not shaped by Christ, it will eventually stand in the way of Christ. Love that feels kind can still block the very growth, healing, and obedience God is working toward.
Speaker: Cameron Mathers,
Series: Hall of Mirrors
Date: 21st Jun, 2026
Download: Unsanctified Compassion
Plays: 0
Views: 18
Sermon notes: 

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Unsanctified Compassion

WHEN LOVE GETS IN THE WAY

Ungodly Compassion vs. God-Shaped Compassion

Sermon Outline & Discussion Guide  |  Matthew 16:13–23  |  Father's Day

Sermon Outline

Big idea: When our compassion is not shaped by Christ, it will eventually stand in the way of Christ. Love that feels kind can still block the very growth, healing, and obedience God is working toward.

Introduction: The Satnav Illustration

  • Picture a satnav set to an “avoidance” mode — no left, no right, no motorways, no people — until it can no longer find any road at all.
  • Love that avoids every cost, risk, or discomfort can do the same thing to a person’s life: it blocks the very path God is offering.
  • Definition: ungodly compassion — love that protects people from the very thing that would make them stronger. Not because love is bad, but because it can be misdirected.

Scripture: Matthew 16:13–23

  • Jesus asks the disciples, “Who do people say that the Son of Man is?” and then, “But who do you say I am?”
  • Peter answers, “You are the Christ, the Son of the living God” — and Jesus blesses him and names him the rock on which the church will be built.
  • Jesus then tells the disciples he must go to Jerusalem, suffer, be killed, and on the third day be raised.
  • Peter rebukes him: “Far be it from you, Lord. This shall never happen to you.”
  • Jesus turns and says, “Get behind me, Satan. You are a hindrance to me. For you are not set on the things of God, but on the things of man.”

Lesson 1 — The Question That Reveals the Heart

  • If we don’t see Jesus clearly, we won’t love people wisely.
  • Everything begins with “Who do you say I am?” — a question about identity, not just religion.
  • How we see Jesus shapes how we see and love everyone else:
  • Only a gentle teacher → we avoid hard truths
  • Only a judge → we avoid compassion
  • Only a comforter → we avoid sacrifice
  • Only a rescuer → we avoid responsibility
  • Ungodly compassion hides truth to spare feelings; God-shaped compassion speaks truth to heal futures.
  • Jesus corrects Peter’s vision before he corrects Peter’s behavior — compassion always flows from who we believe Jesus is.

Lesson 2 — Revelation Builds True Compassion

  • Emotion may feel like love, but only truth knows how to love.
  • Peter is practical and well-meaning — the same instinct that drew his sword in the garden also made him resist the cross.
  • Peter was looking at the present; Jesus was looking at eternity.
  • Emotion reacts; revelation responds. Emotion protects people from discomfort; revelation prepares people for growth.
  • Illustration: a parent who ties a child’s shoe forever isn’t helping — they’re preventing strength.
  • Ungodly compassion gives comfort; only God-shaped compassion gives healing.

Lesson 3 — The Cross Tests Compassion

  • Real compassion must embrace the cross, not avoid it. If compassion avoids the cross, it becomes opposition.
  • Jesus reveals the road: following God involves real cost — loss, sacrifice, obedience that hurts.
  • Peter means well, but “meaning well is not doing well.”
  • “Get behind me, Satan” — Jesus isn’t calling Peter evil; he’s naming the role Peter has stepped into: an accuser pulling Jesus off God’s path.

Where Misdirected Love Shows Up Today

In personal relationships

  • Protecting people from consequences
  • Avoiding hard conversations
  • Rescuing people God is trying to grow
  • Prioritizing peace over truth

In the church

  • Avoiding hard truths and accountability
  • Avoiding calling sin what it actually is
  • Prioritizing attendance over transformation and discipleship
  • Weak compassion produces weak people; God-shaped compassion produces a whole person.

The “Get Behind Me” Moment

  • Peter tried to protect Jesus from the cross; Jesus embraced the cross to save Peter.
  • Jesus didn’t just die for us — he died instead of us.
  • Parenting illustration: stopping a toddler from touching an electrical socket, or letting go of the bike seat so a child learns to ride — love sometimes means allowing discomfort, not preventing it.
  • Reflection questions raised in the sermon: Where am I protecting someone from the growth God wants for them? Where am I resisting God’s path because it’s uncomfortable? Where has my compassion become a hindrance?

Closing Charge

  • Love people towards the cross, not away from it.
  • Love people into obedience, not out of it.
  • A child needs love and correction; an adult needs courageous truth — God gives both.
  • He loves us too much to protect us from the cross; he sent his Son to carry it and calls us to follow

Unsanctified Compassion

Cameron Mathers,
21st Jun, 2026 1:33 pm

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ABOUT THE AUTHOR - ANDY MOYLE

Andy planted the Gateway Church in Sept 2007. He and Janet love to gather different nations together to grow in Christ while eating good food! He also helps to shape and serve a couple of Relational Mission's church plants in mainland Europe. Andy and Janet run regularly, largely to offset the hospitality eating! He also runs a popular WordPress plugin Church Admin