A few years ago, my wife served at Vision of Hope, a residential treatment center for women at risk. During her time on staff, we met many gals from backgrounds of horrific abuse, numbing addictions, and life-debilitating decisions. These gals came wrecked and desperate for change. Miraculously many of those gals intersected with Jesus, began listening to the Bible, and transformed from inside out. You would never know today the history many of these gals had because Jesus had forgiven them and set them free. Jesus loves rescuing risky women.

In the gospel of Luke, we see Jesus mingling with some risky characters like Levi the tax collector who invites Jesus to a party with his buddies (5:27-32), a leper (5:12-26), and a crazed demon possessed man (4:31-44). Jesus reaches out to people most would consider keeping at a distance. In Luke 7:36-50, Jesus intersect with a risky woman in the oddest of places, a religious leaders home. This story begs us to ask the question, which character do I most resemble?

Let’s meet Simon. Simon is a Pharisee. He’s an elite Jewish leader who is known for being a stickler about the law, sort or like the religious rules police. For an unknown reason he invites Jesus over to his house for a meal. Jesus accepts. As Jesus arrives Simon insults Jesus by ignoring to greet Him or give Him water to wash His feet. Simon has a some chip on his shoulder.

It’s not just Jesus he disrespects, he labels a woman. Sure, she’s an unexpected guest and a ‘woman of the city’ who would never be invited to Simon’s house or these kind of parties. He makes a rash judgment about the woman saying, “She is a sinner.” (v.39) Simon has no sympathy for sinners.

Religious people are slow to see others needs, but they are quick to spot others sins before their own

Simon thinks that since he keeps the rules he’s a good man. Compared to his uninvited guest he appears pretty good. Simon is good; good at seeing the flaws in others. He can spy a sinner miles away, all the while camouflage his soul to the public. He does not see himself as a sinner nor his own need of forgiveness. However, Jesus has x-ray vision and sees the condition of Simon’s heart. It’s inhospitable, unloving, irreverent, and unforgiven.

In what ways are you like Simon the Pharisee? Be honest. Is your standard of goodness comparing yourself to others? Have you held back the gospel from ‘sinners’? Are you quick to judge and slow to compassion? If you answered ‘yes’ to any of those questions you have some similarities to Simon.

Simon blew an opportunity to show grace and compassion to this woman. He could have said, “Welcome! I want to be the first to introduce you to Jesus!” Instead, he labels, judges, and belittles her. He despises both woman and Jesus. He despises her despicable reputation and Jesus’ growing reputation. He despises the way the woman worships Jesus because he doesn’t know who Jesus really is.

Those who know who Jesus really is are not ashamed to respond to Him with humble, generous, repentant worship

This woman has a lot to be ashamed about, but she unashamedly approaches Jesus at Simon’s house. She risks her pride and already diminished reputation to see Him there in public, of all places. It is obvious she put thought her actions. She kisses Jesus’ feet, washes them with her tears, and puts ointment on them (vs.37-38). It might appear to be an awkward or offensive situation, but to Jesus it’s beautiful, generous, humble, repentant worship.

Jesus does not rebuke the woman, instead He approves of her humble extravagance. Jesus loves worship. The only thing that matters in worship is God’s approval. He created you for His glory and praise. “For of Him and through Him and to Him are all things, to whom be glory forever.” (Romans 11:36) “For by Him all things were created that are in heaven and that are on earth…All things were created through Him and for Him.” (Colossians 1:16) “Everyone who is called by My name, Whom I have created for My glory.” (Isaiah 43:7)

In response to the woman, Jesus shows love and gives her the most hopeful words, “Your sins are forgiven” (v.48). Can you imagine what those four words meant to her? How life-altering they would be?

In what ways are you like the woman of the city? She does not hold back from worshiping Jesus. She knows who Jesus is and what He can do for her. What she needs is forgiveness. She faces her sin. She does not run or hide. She finds forgiveness in Jesus.

Jesus came to earth to challenge the religious status quo and transform you from the inside out

As I said in the beginning, this story begs us to ask the question, which character do I most resemble? It is common to compare yourself with Simon or the woman, but in what ways are you like Jesus? Jesus is the main character of this story. He’s the star of the whole Bible. In this particular story there is a lot to be learned from Jesus. He accepts both the sinner and the saint. He gives both what they need. To the sinner He gives her forgiveness and assurance. To the one who thinks he’s a saint he gives truth in love. Jesus challenges the the religious status quo. Here’s how:

First, Jesus challenges our flawed perception of our own goodness (vs.41-42). Simon thought he was a good man, especially compared to the woman, but compared to Jesus he looked quite putrid. Jesus reveals the condition of Simon’s heart: polished on the outside, but tarnished on the inside. By the worlds standard’s the Simon is a good man and the woman is bad, but Jesus sees them both equally as sinful and needing forgiveness. Remember, Jesus is our standard of goodness not another sinner.

Second, Jesus challenges our shallow values (vs.44-47). The Pharisee sees himself as an important person. In contrast, the woman humbles herself to show what she deems important. The woman gives Jesus her most precious object in the world because she believes Jesus is the gift of forgiveness will be the most precious gift to her. By breaking the alabaster flask, she is handing over everything that is important to her. Jesus becomes her most valued treasure.

Third, Jesus challenges our sense of safety and certainty (vs.48-50). Simon finds safety and security in his religious system. Following rules is the easy part, but it settles for a lesser status quo than following the way of Jesus. Jesus sets the bar. He shows how you can love the law, yet love others who don’t measure up to it. Jesus’ love for the woman trumps the label Simon puts on her.

If you are into safety and certainty, you will miss God and will miss an opportunity to speak the gospel into a persons life. Religious systems call for conformity to the system, but the gospel calls for transformation through Christ alone. The one thing that is certain in this world is Jesus. He is the way, the truth, and the life. No one gets to God but by Him. He is the standard of goodness. And no one measures up. But by His grace you can be saved because Jesus took all your badness on the cross. Come to Him and be forgiven. Let Him change you from the inside out.

Who do you most resemble in this story? You are the pharisee when you forget you are like the woman. Do you believe you are a sinner, or do you think you’re basically a good person? Do you know that Jesus has forgiven your sins? If so, how can you be loving and serving Jesus, at home, at school, in your neighborhood?