Jesus, Simon, and a Sinful Woman (Luke 7:36-50)

Intro: Have you ever been in an uncomfortable situation by the company of worldly people? At times, when we find ourselves among the lost of the world, things can be a bit awkward. Gardner Hall (preaches in downtown Manhattan) relates the time when he went to open the door of the building in Upper Manhattan. A woman, obviously a prostitute was sitting on the front step. He said he thought of Jesus and tried to be polite. He considered inviting her in for our study as he did with others whom he found hanging around at the time of assembly. But he also thought how embarrassing, or at least awkward, it would be if she accepted the invitation and came in and study with the brethren dressed as she was, knowing what kind of woman she was!

One of the points of controversy between Jesus and the Pharisees centered on how the righteous should view the unrighteous. How involved should we be with the world? Jesus has some lessons for us in the context of the controversy.

Read Luke 7:36-50. Sometimes we need to be uncomfortable to learn the needed lessons. Jesus used several uncomfortable situations like this to teach great truths. This is the story of Jesus, Simon, and a sinful woman.

Customs that help us understand this event: (David Padfield)

  •  When a Rabbi was at a meal in a house with a courtyard, all kinds of people came in to listen to the words of wisdom that fell from his lips.
  • According to custom, when a guest entered such a house the host placed his hand on the guest’s shoulder and gave him the kiss of peace. That was a mark of respect that was never omitted in the case of a distinguished Rabbi. This helps us to understand why Judas betrayed Jesus with a kiss (Matt. 26:48-49).
  • Cool water was also poured over the guest’s feet to cleanse and comfort them, and either a pinch of sweet-smelling incense was burned or a drop of rose oil was placed on the guest’s head. These things good manners demanded.
  • In the east the guests did not sit at a table — they lay on low couches, resting on the left elbow, leaving the right arm free, with the feet stretched out behind; and during the meal the sandals were taken off — this explains how the woman was standing beside Jesus’ feet.

Analyzing the Characters:

I. Simon, the Pharisee: At the beginning of the story we only see him as “the Pharisee” who invited Jesus into his house. Later in verse 40 Jesus called him by his name, Simon.

A. Even though Simon doesn’t look too flattering here, doubt he was a “bad guy.

1. He was hospitable in the sense of the invitation. “It seems he was interested in knowing more about Jesus and possibly learn from Him. Jesus recognizes Simon ability and willingness to learn the lesson He teaches here. (Sometimes Jesus refuses to even respond to the Pharisees’ hypocrisy).

B. Why would Simon withhold common courtesies? Was Simon testing Jesus as to the public opinion that He was a prophet from God. After Jesus raised the widow’s son, “…fear came upon all, and they glorified God, saying, “A great prophet has risen up among us”; and, “God has visited His people.”, 17 And this report about Him went throughout all Judea and all the surrounding region. Luke 7:16-17 There is no indication that Simon invited this woman to his house for this purpose, but the circumstance became a test for him in his decision about Jesus…( If He were a prophet…”)

1. Was Simon being careful not to honor Jesus too much for fear of angering his fellow Pharisees?

II. A Sinful Woman: vs. 37 – “a woman in the city who was a sinner”.There some who suppose that she was a prostitute, but that is not certain. Adam Clark indicates the many times where this word “sinner” (hamartoolos) Is used to describe those who were Gentiles, and thus viewed as sinners by the Jews. (Matthew 9:10-11 – Jesus sat down with “tax collectors and sinners.”) Zacchaeus is described with the same word.) She is obviously a woman with a bad reputation. It was not Mary Magdalene, Nor is it Mary, sister of Martha and Lazarus. Her anointing occurred later.

A. Why would she have wanted to come in? She may have heard Jesus teach and been drawn to become a follower. Jesus’ statement about why she did what she did would point to her previous conversion and repentance. Some place this event immediately following Jesus’ invitation in Matt. 11:28“come unto me all you that labor and are heavy laden and I will give you rest.” She is confident that Jesus will accept her.

B. Alabaster flask of perfume (NAS). This oil was much more expensive than common oil. She showed a lot of emotion: Crying, kissing his feet, touching Him.

1. You can easily imagine the discomfort of the people to what they would have considered an embarrassing outburst. Have you ever been in a situation where someone else was showing too much emotion for you? There was probably an uncomfortable silence, eyes rolled upward. Simon is thinking, “Why in my house?”

2. And yet as most in the house cringing with discomfort, Jesus calmly accepted this display of emotion and affection as something acceptable and appropriate.

III. Simon’s Critical Thoughts: vs. 39– Now when the Pharisee who had invited Him saw this, he spoke to himself, saying, “This Man, if He were a prophet, would know who and what manner of woman this is who is touching Him, for she is a sinner.” Is he just going to let her act this way?

A. The Pharisee expected Jesus, as a wise rabbi and a religious leader, to reject the woman’s attention as insulting. The rabbis of that time never talked with a woman in public if they could help it.

1. Simon questions in his mind Jesus’ credentials as a true prophet. The literal rendering of his thought is… “If he were a prophet-but that he cannot be”.

IV. Jesus Simple Illustration: (Vs. 40-43) Simon had not voiced his objection, so Jesus’ words may have first appeared as simple dinner conversation, or Jesus’ desire to seek Simon’s input on a question concerning stewardship. I think He considered Simon sincere, worthy of this simple yet profound illustration. So he uses this awkward moment to teach him a lesson.

A. Two debtors who cannot pay, so the master forgives them both. One owes 10 times more than the other. The analogy is between a material debt and sin. There may be some implied lessons here:

1. We all owe God, and none can pay. He forgives sin freely. We do not pay it off. In that sense our debts are equal, even though our sin is not. But what is Jesus’ application?

B. vs. 42 – “Tell Me, therefore, which of them will love him more?” Jesus is relaying to Simon why this woman would react with such an emotional display of gratitude. She had been forgiven. And her debt was great (Simon would certainly have no problem putting her in that category – She owed God a lot.)

Some Other Applications

1. One element of this story that we should not miss is the ability of Jesus to know what is in everyone’s heart.

  • He knows why this woman is doing this. He knows why she is crying, and what she feels toward Him
  • He also knows what is in Simon’s heart. His initiation and pleasantry cannot hide what he was thinking from Jesus. He confronts Simon subtlety, yet directly.
  • God knows our hearts, and He sees our motivations. Does Jesus see Me as good as I see myself?

2. Some people associate with Jesus for ulterior, insincere reasons. Simon wanted Jesus to eat in his home, but he had no perception of needing Jesus. He was only casually interested. He did not even offer the customary courtesies of the day. The woman, however, knew exactly why she was there. She was there to honor Jesus in a display of emotion. He felt a real spiritual need for Jesus.

  • Some people act interested in Jesus but really aren’t motivated by deep spiritual need. They may pray at meals, attend services, read Bible, and enjoy the company of good people but aren’t devoted. They allow other things to take precedence. There is no genuine sense of what god has done for them. she does not hesitate to do the work of a servant. She is not embarrassed.
  • The woman was not embarrassed to weep or do the work of a servant. Simon, however, seemed embarrassed to offer even basic hospitality.
  • He withheld water, she used tears; he withheld a kiss, she kissed His feet; he did not anoint Jesus with common oil but she rubbed His feet with expensive, perfumed oil.
  • Some people are hesitant to be baptized in front of others; they carefully measure their response so as to retain their dignity. But when we realize that our sins make us God’s enemy and forgiveness makes us His friend, then we will gladly render uninhibited obedience.

3. Our ability to love God as we should is rooted in our recognition of our forgiveness. Those who are forgiven much love much. Spiritual development hinges on this point. 2 Peter 1:5-95 But also for this very reason, giving all diligence, add to your faith virtue, to virtue knowledge, 6 to knowledge self-control, to self-control perseverance, to perseverance godliness, 7 to godliness brotherly kindness, and to brotherly kindness love. 8 For if these things are yours and abound, you will be neither barren nor unfruitful in the knowledge of our Lord Jesus Christ. 9 For he who lacks these things is shortsighted, even to blindness, and has forgotten that he was cleansed from his old sins.

4. Pride leads us to misjudge ourselves and others. Simon’s self-righteous pride caused him to misjudge Jesus. That was a critical mistake. Jesus was more than a prophet. He was one who could forgive sins! He also misjudge the woman. He saw her as a hopeless sinner to be avoided. Jesus showed her to be one was right before God – forgiven of all of her sins.

  • we may allow our vaulted opinion of ourselves convince us that those who are not like us cannot be right with God. We ignore that sinners who are seeking to be forgiven, or who have been forgiven by Jesus.
  • But Simon’s first misjudgment was about himself – He did see himself as a debtor who need to be thankful for being forgiven.

5. Two opposing approaches to Jesus: These two individuals: Simon the Pharisee, and the woman represent two ways to approach Christ.

a. Simon’s approach was through a sense of obligation alone. It was courtesy mixed with concern for what others think. His approach was careful and calculated.

b. The sinful woman’s approach was through a true hunger and thirst for forgiveness. It was a display of enormous gratitude and love that could not be hidden and was not concerned with what others thought.

We see these two forms represented today.

  • Some come, like Simon in a sense of obligation; “I’m a Christian, have to go to services,” . Worship often becomes routine and has not impact on real life. (This attitude is often seen among second, third generation Christians)
  • Others come like the woman, with an unstoppable desire to be close to the One who saved them. They do not have to chided to give their best to the Lord –They do it out of love.

The main difference between the two approaches?

  • Simon had no sense of forgiveness. He didn’t realize how much he needed Christ. There was no love.
  • The sinful woman realized she was nothing without Christ and His forgiveness. She was truly “poor in spirit” (Matt. 5:3) She realized she was spiritually bankrupt. She loved Jesus much.
  • God’s Kingdom is made up of people like her. This is the true key to spirituality. If we want to approach Christ like the woman, we must constantly consider our need for Him. Even though we’ve been baptized, attend services, know issues, when we compare ourselves with Christ, we are nothing.
  • Sincere, unabashed love that comes from a true appreciation for forgiveness is worth more to God that a long list of obeyed rules. A broken heart is worth more than a good checklist! Of all the people crowded into that house, one went away forgiven. Who? The ones who had faithfully attended synagogue many years, never missed service? The ones who strove all their lives to interpret the law correctly? Doctors, professors, knew the law from cover to cover? The one forgiven, was the one with the bad reputation, the sinful woman!

Conclusion: Can you see yourself in this story? Do you more easily fit the part of Simon or the sinful woman? I am humbled and stricken by the answer. Let us leave behind pride, self sufficiency, and self righteousness and come in true contrition to anoint the feet of Jesus with our love and gratitude.