SERIES: Jesus Loves People
MESSAGE: Jesus Loves Prostitutes
SPEAKER: Skip Heitzig
SCRIPTURE: Luke 7:36-50

It was Blaise Pascal who noted, "There is a God-shaped vacuum in the heart of every man which cannot be filled by any created thing, but only by God, the Creator, made known through Jesus." In our text today, we find a woman, the city prostitute who acutely felt the need to have the vacuum of her heart filled. She discovered that Jesus loved her with a wholesome love—the kind of love every woman is searching for.


Prostitution is mentioned frequently in Scripture; the word harlot is used seventy-six times (with primary references in Leviticus 19, Proverbs, and 1 Corinthians 6). Two prostitutes even appear in the genealogy of Christ: Tamar and Rahab. Jesus pointed out that prostitutes were among those who repented at the preaching of John the Baptist (see Matthew 21:32), and He shocked the religious leaders by telling them that "tax collectors and harlots enter the kingdom of God before you" (Matthew 21:31).

Research into modern-day prostitution is heartbreaking. The sex trade is big business; in Miami alone, it's a $235-million-a-year industry. One in ten men in the world have purchased a prostitute. The average age of entry into prostitution is thirteen, the overwhelming majority being girls. Most are recruited or coerced into prostitution and are especially targeted within forty-eight hours of running away from home. It's a deadly job; statistics for job-related fatalities measure 18 deaths per 100,000 for police officers, 70 per 100,000 for airline pilots, and 204 per 100,000 for prostitutes. Over 95 percent have been threatened with a gun or beaten, and over half have been assaulted or raped. Our text tells us of a meeting between Jesus and a prostitute at the house of Simon, a Pharisee. Three distinct interactions occurred that show us the pitfalls of self-righteousness and the power of forgiveness.

First, we consider the interaction between the patriarch—Simon—and the prostitute (see Luke 7:36-38). Most likely, Simon invited Jesus over in order to interrogate Him. However, when a prostitute barged in, the center of gravity shifted. It was unusual for such a woman, a "sinner" (in those days, this word could only mean a prostitute), to be at such a meeting, and only Jesus welcomed her. Weeping, she loosened her hair and kissed Jesus' feet, pouring oil on them. We don't know the depth of her pain or why she became a prostitute, but we can guess why she was there. It's possible that, shortly before this meal, she had heard Jesus preach, "Come to Me, all you who labor and are heavy laden, and I will give you rest. Take My yoke upon you and learn from Me...and you will find rest for your souls" (Matthew 11:28-29). She understood that Jesus was her best shot at a new start. A prostitute once said, "Prostitutes have very improperly been styled women of pleasure; they are women of pain, of sorrow, of grief, of bitter and continual repentance." Ignoring Simon's disdain, this prostitute rushed to Jesus, weeping from remorse and pain, desperate for hope. Read 2 Corinthians 1:3-7. Have you ever been desperate for God's forgiveness and love? How can that experience help you have compassion for someone like this woman?

Next, we see the patriarch and the preacher (see Luke 7:39-47). Simon mistook this woman's act of repentance and devotion for a sexual advance and criticized Jesus in his thoughts. Jesus read Simon's mind and replied to him out loud. The story Jesus then told revealed that Simon had a wrong view of everyone at the meal. In Simon's mind, Jesus was not a prophet, the woman was too sinful and filthy to be there, and he, Simon, was the most discerning person in the room. Jesus' story revealed that Simon's manner was inhospitable, his heart was judgmental, and his sin was invisible (hers was outward, and his was inward—until Jesus called him out on it). Like Simon, when we view life through the lens of legalism, we distort everyone and everything. Jesus rebuked him for not being as broken about his sin as she was about hers. Religion is the world's biggest blind spot in seeing our need for God; religion made Simon inhospitable to Jesus, judgmental toward this woman, and prideful in his attitude. The prostitute's sins were sins of the flesh; Simon's were of the spirit. Hers were overt and known to all; his were covert, known only to Jesus. What Simon saw insulted him, but what he heard should have convicted him. Describe a time when you have been unfairly judgmental. How did God bring you to a point of repentance?

Finally, we see the preacher and the prostitute (see Luke 7:48-50). Jesus was now face to face with this woman whose face was riddled with tears and shame, and He declared to her that her sins were forgiven. How wonderful she must have felt then! Jesus was not put off by her reputation, His knowledge of her past, or even Simon's judgment of her. Jesus knew that her heart was broken, filled with shame and remorse, and that she hated her lifestyle and wanted change. Others in the house were angry because Jesus told her that she was forgiven, but she was not angry—she was hungry. They were self-righteous; she was made righteous. The love she never found in all of her passionate encounters with men she now found in a single encounter with this unique Man, Jesus Christ. She learned that God has a big eraser. Simon's sin got exposed; this prostitute's sin got forgiven. Simon had years of theological training and yet no understanding of grace. She understood it after a few moments in Jesus' presence. Read Romans 5:20-21. What are the dangers of being self-righteous? How big is God's grace? How can you show grace when you meet someone who, on the surface, seems unworthy of it?

Here are three takeaways from this passage: First, everyone sins; face it. "All have sinned and fall short of the glory of God" (Romans 3:23), and the worst sin of all is self-righteousness—it's an affront to the cross of Christ. Second, God's business is forgiveness; seek it. This woman knew that she was a great sinner, and she came to Jesus as her great Savior. Finally, God's Word is true; believe it. Jesus spoke a promise to this woman that she was saved and forgiven. Your sin can be forgiven, too!

Adapted from Pastor Skip’s teaching

The BIG Idea We all need forgiveness. God stands ready to forgive any sin, from prostitution to self-righteousness.


  1. Introduction
    1. "Everybody is ignorant, only on different subjects"—Will Rogers
    2. The Bible talks about prostitution
      1. Speaks of harlotry seventy-six times
      2. Condemned as immoral
      3. Leviticus 19; Proverbs; 1 Corinthians 6
      4. Prostitutes were among those who listened to John the Baptist and repented
      5. Matthew 21:31-32
      6. Two prostitutes are in the genealogy of Christ
        1. Tamar and Rahab
        2. Hebrews 11:31
    3. The sex trade is a huge moneymaking enterprise
      1. Miami: $235-million-per-year industry
      2. 10 percent of American men buy sex; one in ten men worldwide
      3. Average age a girl gets involved: thirteen years old
      4. One in ten kids aged ten to eighteen run away from home
    4. Prostitution is one of the deadliest professions in the world
      1. Mortality rate of average American worker: 3.5 people per 100,000
      2. Police officers: 18
      3. Aircraft pilots: 70.6
      4. Deep-sea fishermen: 75
      5. Prostitutes: 204
        1. 95 percent are threatened with a gun or beaten
        2. Over half will be assaulted or raped
    5. Before we harshly judge an immoral lifestyle, we need to understand how someone was introduced to it, when they got into it, and what's currently threatening them
    6. Jesus Christ and a prostitute in the home of a Pharisee
    7. The Pharisee and the prostitute were drawn to the compelling person of Jesus Christ
  2. The Patriarch and the Prostitute (vv. 36-38)
    1. We don't know why Jesus was invited to the Pharisee, Simon's, house
      1. Perhaps out of curiosity
      2. Perhaps Simon wanted a feather in his hat by having Jesus over
      3. Simon wanted to trap Jesus
    2. What Martin Luther called "heart water" came from the woman
    3. It was not unusual to have uninvited people at dinners like this
      1. But it was unusual for this woman to be there, a "sinner"
        1. A female in that culture with the title "sinner" meant she was a prostitute
        2. New Living Translation: "a certain immoral woman"
      2. You couldn't get two more different people in one room than Simon and this woman
      3. The Talmud: for a woman to let her hair down in front of another man was grounds for divorce by her husband
      4. The Pharisee would have seen her touch as a sexual advance
    4. Why did the woman come?
      1. Because Jesus was there
      2. She must have heard who He was or even heard Him preach
      3. Matthew 11:28-29
      4. She wanted real love
      5. "I don't know what real love is. I don't know what it looks like, feels like, acts like. The only kind of 'love' I have ever had is the one-way kind, the kind that is paid for in goods and services, and evaporates like dew in the morning, or explodes into violence in the middle of the night. I don't know what it's like to love and be loved"—Laura Schulman
      6. We don't know the depth of pain and remorse this woman was experiencing, or when or why she got involved in prostitution
      7. "Prostitutes have very improperly been styled women of pleasure; they are women of pain, of sorrow, of grief, of bitter and continual repentance"—Anonymous prostitute
  3. The Patriarch and the Preacher (vv. 39-47)
    1. Simon mistook an act of devotion, worship, and repentance for a sexual advance
      1. The word for touching (v. 39) is a strong word meaning a sensual touch
      2. You have to be coldhearted to think that way
    2. Simon had a wrong estimation of everyone in the room
      1. He thought Jesus was no prophet, when He really was the Prophet
      2. He thought the woman didn't belong there with Jesus, when that's exactly where she belonged
      3. He maybe thought things like I wish others were as discerning as I am
      4. When you view life through the lens of legalism, everyone and everything you see is distorted
    3. The name Simon means one who hears
    4. Three things about Simon we get from Jesus' words
      1. Simon's manner was inhospitable
        1. Common protocol was to wash the feet of guests
        2. Kiss on both cheeks
        3. Give them a scented olive oil
      2. Simon's heart was judgmental
        1. Rabbis loved to tell stories
        2. Neither Simon nor the woman could owe the debt they paid to God
        3. Why? Because of his religion
        4. Religion is the world's biggest blind spot when it comes to people knowing their need for God
      3. Simon's sin was invisible
        1. Her sin was outward: a sin of passion; his sin was inward: a sin of pride
        2. Hers was sin of the flesh; his was sin of the spirit
        3. Hers was overt; his was covert
        4. In Western evangelicalism, we have socially acceptable sins: gluttony, greed, gossip
    5. What Simon saw of the woman insulted him, but what he heard Jesus say should have convicted him
  4. The Preacher and the Prostitute (vv. 48-50)
    1. Jesus was not put off by her reputation, her past, or by the judgment of others on her
    2. Others in the house were angry at Jesus promising forgiveness, but that woman was hungry for that promise of forgiveness
      1. They were disgusted; she was delighted
      2. The love she never found in all her passionate encounters with men she found in a single encounter with this unique Man, Jesus
    3. God has a big eraser
    4. Simon got his sin exposed; this woman got her sin forgiven
      1. Simon had theological training but didn't know anything about God's grace
      2. She spent a few moments in Jesus' presence and she knew more about God's grace than most believers today
  5. Closing
    1. Everyone sins; face it
      1. Romans 3:23
      2. We all flunk the righteousness test, but most people think God grades on a curve
      3. The worst sin is self-righteousness because it's an affront to the cross of Christ
      4. "A scab is a scab even if you smear honey over it"—Yiddish proverb
    2. God's business is forgiveness; seek it
      1. Simon was unaware of his need and therefore uninterested in forgiveness
      2. The woman knew that she was a great sinner and that Jesus was a great Savior
    3. God's word is true; believe it
      1. The woman had to walk away believing that what Jesus said was true
      2. The moment she said, "I believe what Jesus said," she became an ex-prostitute
    4. Tina Hoffman; Romans 5:8
    5. We've all fallen short of God's glory, and the only medicine is God's forgiveness; it does no good to keep the medicine on the shelf of heaven

Figures referenced: Will Rogers, Martin Luther, Laura Schulman, Tina Hoffman

Cross references: Leviticus 19; Proverbs; Matthew 11:28-29; 21:31-32; Luke 7:36-50; Romans 3:23; 5:8; 1 Corinthians 6; Hebrews 11:31

Topic: Forgiveness

Keywords: prostitution, harlotry, sex, sex trade, Pharisees, love, legalism, judgment, judging, religion, sin, sinner, passion, flesh, self-righteousness, forgiveness, grace

Jesus Loves Prostitutes - Luke 7:36-50 |
Page |