Luke 7:36-50 / The Cost of Sin and the Value of Forgiveness
It is an honor to be here today, and I thank you for that.
In 1991, I turned 16 and I got my driver’s license. I’ll let you do the mental mathematics on that one. At the age of 16, my parents handed me the keys to a car. Now, if you’ve watched any movies, you know it wasn’t the kind of car you’d probably expect. In the movies, everybody gets a Corvette with a big red bow on top, or a Lexus. My parents gave me the keys to a 1975 Chevy Malibu Classic. Oh yeah, you know the one.
It was seventeen and a half feet long. It had two doors—not two on each side, just two massive doors for a seventeen-and-a-half-foot car. The headlights, from some accident that took place before my time, were all cattywampus, so they were kind of looking at each other and then cross-eyed at the other drivers. Inside, it had bench seating for comfort and leisure. The three seats in the front had lap straps, because that was totally safe, and the three in the back had nothing—it was like, “Forget about them; they don’t need seatbelts.” Two benches meant six people legally, but we would usually cram in a few more for fun.
This car had survived brutal Ohio winters, so the road salt had completely eaten away at the paint and metal. The thing was rust from front to back, except where a little bit of “Sherman tank green” paint remained. I had my license before most students on campus, so that car became the car. I was the one driving everybody to lunch and to friends’ houses. Over time, it became known as the “campus clunker.” We crammed anything we could find into the rust holes—American flags shooting out of the sides, squirt guns mounted like gun turrets with people sitting on top. (All things I had my parents’ permission to do, by the way, students!) We caused a little havoc, but that car was loved in the roughest sense of the word. It was loved and abused.
The Cost Determines the Value
A couple of cars later, I drove a 1995 Geo Metro off the lot. I know, you’re impressed. It didn’t have two doors; it had three—one on each side and a hatchback. It wasn’t seventeen and a half feet long; it was about seven feet long. I’m not a huge guy, but I’m six feet tall, and I had to fold myself into that car every single time. Jen Bell affectionately called it “the blue Skittle with wheels.” I drove that thing for a long, long time.
Now, let me ask you: what was the difference between these two cars? We would all agree that the ’75 Malibu Classic, though rusted out, was arguably a much better car. Yet I took drastically better care of that ’95 Geo Metro. “Hey guys, when you get in, could you wipe your feet? Be careful. No, you can’t eat in here—this is a Geo Metro! Take care of this investment!” I kept my hands at ten and two, made sure the tires were rotated, and looked after it.
Why the difference? The Geo Metro cost me something. I paid for it. I put the down payment down, and I made those monthly payments. Every single month, I felt the cost of that car. Even though it was basically half a car, it mattered deeply to me.
It is true for all human beings: we assign value to things based on what they cost us. If something costs us nothing, it holds considerably less value. And that is the exact point Jesus makes to us in tonight’s parable. He wants us to see that if we have a low view of our sin—if we minimize what we have done against God and treat our sinful condition lightly—then His forgiveness will hold very little value for us. We simply won’t see it as important.
Tonight, we are continuing our summer series on the parables. As we’ve learned, Jesus’ parables always contain two key elements. First, as Dave Obald shared about a month ago, there is a shocking element. Jesus tells a story that seems obvious, and just when the listeners think it’s heading one way, He takes a sharp turn that completely blows their minds. Second, His intent is to shock people out of their existing value system, driving them toward genuine life change. He wants them to stop living according to the world’s standards and start living according to the Kingdom of God.
Tonight, Jesus is at it again. He tells a story addressing sin and its cost, challenging both His original listeners and us today: What do you truly value? What do you believe your sin has cost you—and what did it cost Jesus?
An Uncomfortable Dinner Party
Turn with me to Luke chapter 7, verses 36 through 50. We’ll read through this passage in sections and unpack it together.
Luke 7:36-40 (NASB)
Now one of the Pharisees was requesting Him to dine with him, and He entered the Pharisee’s house and reclined [at the table]. And there was a woman in the city who was a sinner; and when she learned that He was reclining [at the table] in the Pharisee’s house, she brought an alabaster vial of perfume, and standing behind [Him] at His feet, weeping, she began to wet His feet with her tears, and kept wiping them with the hair of her head, and kissing His feet and anointing them with the perfume. Now when the Pharisee who had invited Him saw this, he said to himself, ‘If this man were a prophet He would know who and what sort of person this woman is who is touching Him, that she is a sinner.’ And Jesus answered him, ‘Simon, I have something to say to you.’ And he replied, ‘Say it, Teacher.’
Before we look at the parable itself, let’s understand the setting. Jesus has been invited to a dinner party by a Pharisee named Simon. Jesus has already been making bold, earth-shaking claims that completely unsettled the religious leaders. He claimed to be sent by God, claimed to be a prophet, and stated that He did not come to abolish the Law, but to fulfill it. When He taught, He would say, “You have heard that it was said… but I say to you…” The Pharisees objected: “Nobody can live up to that!” And Jesus replied, “Exactly. You can’t. No human being can do it on their own, and that is why I am here—to fulfill the Law.”
These religious leaders had devoted their entire lives to studying the Scriptures, observing every rule, and building a system of self-righteousness. Jesus was turning their whole world upside down, and they were frustrated. So they invited Him over.
Mike did a phenomenal job two weeks ago explaining these kinds of cultural settings. While Mike spoke on a synagogue setting, tonight’s story takes place in the private home of a Pharisee. In that culture, prominent religious teachers would host dinner parties where they would debate the Torah back and forth. They would volley scriptures across the table, impress each other, puff out their chests, and feel good about themselves. These events were public spectacles, much like an open academic debate where students and onlookers gathered around the edges of the room to observe without joining the table.
Simon and his friends invited Jesus, but this was not an honest religious dialogue. This was a spiritual ambush—a religious mugging. They wanted to put Jesus in His place, demonstrate that He was not their equal, and give Him enough rope to hang Himself so they could prove He wasn’t a true prophet.
Their hostility was evident the moment Jesus arrived at the door. In that culture, when a guest walked dusty roads to your home, customary hospitality required three basic courtesies. First, you provided water and a servant to wash their hot, dusty, sweaty feet. Simon offered no water. Second, you welcomed them warmly with a holy kiss on the cheek, signaling brotherhood and affection. Simon gave Him no greeting. Third, you anointed their head with olive oil to refresh them and make the gathering pleasant. Simon offered no oil.
By intentionally withholding these basic courtesies, Simon and his friends publicly disgraced Jesus before He even sat down. They sent a crystal-clear message: You are unclean, you are inferior, and you do not belong among us. Yet Jesus quietly walked in and reclined at the table.
Tears, Hair, and Broken Alabaster
As the onlookers watched the debate begin, a woman from the city entered the room. Scripture identifies her as a “woman of the city, who was a sinner”—almost certainly a known prostitute. In that society, she was considered an outcast: unclean, despised, and rejected by polite religious company.
Yet the text tells us that when she learned Jesus was reclining at the Pharisee’s house, she came prepared. The Greek verb indicates she knew in advance where He would be. She had likely heard Jesus teach before. While the Pharisees told her she was hopeless and irredeemable, Jesus offered her forgiveness and life. She took an alabaster flask of expensive aromatic ointment and brought it to Simon’s house just to be near Him.
Standing behind Jesus at His feet, she watched the Pharisees dishonor Him. She saw that the only man who offered her real hope was being treated with cold contempt. Overcome with grief and love, her emotions broke open. Tears began pouring from her eyes onto Jesus’ dusty feet.
She hadn’t planned to wash His feet—that was the host’s job. But seeing His feet unwashed, she did the only thing she could: she fell to her knees, wet His feet with her tears, and unbound her hair to wipe them dry. In that culture, for a woman to let down her hair in public was scandalous, but she didn’t care. She showered His feet with kisses of deep gratitude, then broke open her alabaster flask and poured the costly ointment over them.
That flask represented her livelihood, her security, and her life savings. Once broken, the container could never be used again. In the eyes of the room, it was a shameful waste. But in her eyes, everything she had belonged at the feet of the only One worthy of it.
Simon looked on in disgust, thinking to himself: If this man were really a prophet, he would know who is touching him. He would know what kind of vile sinner she is, and he would never allow it.
Jesus, knowing Simon’s very thoughts, said, “Simon, I have something to say to you.”
Simon replied, “Say it, Teacher.”
The Parable of the Two Debtors
Luke 7:41-43 (NASB)
’A moneylender had two debtors: one owed five hundred denarii, and the other fifty. ‘When they were unable to repay, he graciously forgave them both. So which of them will love him more?’ Simon answered and said, ‘I suppose the one whom he forgave more.’ And He said to him, ‘You have judged correctly.’
To understand this parable, we have to understand what debt meant in the ancient world. Debt back then wasn’t a high credit card balance, a short sale, or filing for bankruptcy. Debt was a matter of life and death. If you could not repay a lender, he had the legal right to throw you into prison, take your life, or force you into indentured servitude.
When a debtor worked as a slave to pay off a balance, he still needed food, clothes, and shelter, which the master added to his account. As a result, debtors often accumulated more debt while trying to work it off, trapping entire families for generations.
Jesus uses two specific figures. The first debtor owes 50 denarii. A denarius was a standard day’s wage for a common laborer. Fifty denarii represents roughly ten weeks—about two and a half months—of wages. In modern American terms, that’s roughly $8,600. It’s a significant burden, but with strict budgeting and hard work, you could eventually pay it off.
The second debtor owes 500 denarii—nearly two full years of wages, or around $86,000 today. For a common laborer, that was an insurmountable, life-crushing debt.
When neither debtor could pay, the moneylender freely and graciously canceled both debts. Jesus looks at Simon and asks, “Which of them will love him more?”
Simon gives a somewhat reluctant, sarcastic answer: “The one, I suppose, for whom he canceled the larger debt.”
“You have judged correctly,” Jesus says.
Seeing the Woman
Luke 7:44-48 (NASB)
Turning toward the woman, He said to Simon, ’Do you see this woman? I entered your house; 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 she, since the time I came in, has not ceased to kiss My feet. ’You did not anoint My head with oil, but she anointed My feet with perfume. ‘For this reason I say to you, her sins, which are many, have been forgiven, for she loved much; but he who is forgiven little, loves little.’ Then He said to her, ‘Your sins have been forgiven.’
In a culture built on honor and shame, Jesus turns the tables. He turns His face toward the weeping woman at His feet, but directs His words to Simon:
“Simon, do you see this woman? I entered your house, and 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 I came in she has not ceased to kiss My feet. You did not anoint My head with oil, but she has anointed My feet with ointment. Therefore I tell you, her sins, which are many, are forgiven—for she loved much. But he who is forgiven little, loves little.”
Jesus exposes the hearts of everyone in the room. Simon believed his sins were trivial and manageable. Because he thought he needed very little forgiveness, he offered Jesus zero honor and zero love. But this woman knew the overwhelming weight of her sin. She knew she was drowning in a debt she could never repay. Because she received extravagant forgiveness, she responded with extravagant, reckless love.
Then Jesus looks down at her and speaks the words that shatter the room: “Your sins are forgiven.”
Extravagant Worship vs. Self-Righteous Comfort
Luke 7:49-50 (NASB)
Those who were reclining [at the table] with Him began to say to themselves, ‘Who is this [man] who even forgives sins?’ And He said to the woman, ‘Your faith has saved you; go in peace.’
The guests at the table immediately began whispering among themselves in shock: “Who is this, who even forgives sins?”
They understood the theological weight of what Jesus just did. Only God can forgive sins. By forgiving her, Jesus was directly claiming divine authority. For the Pharisees, this was another nail in the coffin—more fuel on the fire leading Him straight to the cross.
Look at the contrast between these two postures. Simon and his fellow religious leaders tried to reason their way to God through intellectual gymnastics, moral performance, and social status. They treated God like an abstract concept or a system to master. Because they felt no weight of sin, Jesus held no value for them.
This woman had reached the absolute end of herself. She knew that moral performance couldn’t save her. She didn’t look around the room comparing herself to others, thinking, Well, at least I’m not as bad as that person. She brought her brokenness, her shame, and her most prized possession, and laid them entirely at the feet of Jesus. Her faith saved her, and she walked away in true shalom—in the deep, abiding peace of God.
My friends, if you are still living in a place where you look at others and say, “Well, at least my marriage isn’t as messy as theirs,” or “I struggle with things, but at least I’m not hooked on what that guy is doing,” you are missing the heart of the Gospel. As long as you compare your righteousness to other people, Jesus will have very little value to you.
If we are honest with ourselves, we usually want to claim we are like the woman. We know that’s the “right” church answer: “I’m a great sinner, and Jesus is a great Savior.” But do our lives reflect that reality? Or do our everyday attitudes look far more like Simon—comfortable, self-sufficient, and cold toward Christ?
We have to wrestle with the question asked at that dinner table: Who is this who even forgives sins?
We answer that question not just with our theology, but with our lives. Is Jesus merely a moral teacher, a nice Sunday routine, and a good suggestion? Or is He the Lord of glory who stepped into our depravity, paid an insurmountable debt on a Roman cross, and washed our souls clean?
At The Well, we always say: You are welcome here. Come as you are. You are deeply loved by the God of the universe. But we also say that we love you too much to let you stay where you are.
My prayer for us is that we would become a people who love God with reckless extravagance. May our worship reflect the immense debt we have been forgiven. As Jesus taught, may we love the Lord our God with all our heart, soul, mind, and strength, and love our neighbors as ourselves. May our appreciation for Jesus grow deeper every single day as we comprehend the true cost of our sin—and the infinite value of His forgiveness.
Let’s pray together.
Father, it is humbling to realize we can even approach Your throne. We have no inherent right to demand Your favor, Your mercy, or Your love. The debt of our sin was overwhelming, yet in Your grace, You chose to cancel it completely through the sacrifice of Your Son. Forgive us for the times we treat our sin lightly and minimize Your cross. Break our pride, Lord. Make our lives an extravagant display of love and devotion for our Savior. In Jesus’ name we pray, Amen.