SCRIPTURE: Luke 7:36-50 (ESV)
DATE: 8-16-26
As always, it’s a joy to be with all of you this weekend at Gateway Church. And there’s one thing I want you to know — and this is true whether you’re worshiping with us for the first time or if you’re joining us at our North Main Campus — I want you to know that God loves you and that I love you too.
PASTORAL PRAYER
INTRODUCTION
We’re continuing our Gospel Project series this weekend. During the summer we’re syncing up our sermons with our Kidway ministry curriculum, which is called the Gospel Project. We thought this would be a good way for those of us without kids in our Kidway ministry to understand what the kids are being taught each week. And they happened to be in the gospels learning about Jesus this summer, which is a great place in the Bible for all of us adults to be — because — the whole Bible is ultimately about Jesus. So what better way to spend our summer than to get to know him better?
And we’re going to be in the gospel of Luke today. We’ll be in chapter seven — looking at verses thirty-six through fifty. Again, that’s Luke chapter seven — beginning in verse thirty-six. There we read…
Luke 7:36–50 ESV
36 One of the Pharisees asked him to eat with him, and he went into the Pharisee’s house and reclined at table. 37 And behold, a woman of the city, who was a sinner, when she learned that he was reclining at table in the Pharisee’s house, brought an alabaster flask of ointment, 38 and standing behind him at his feet, weeping, she began to wet his feet with her tears and wiped them with the hair of her head and kissed his feet and anointed them with the ointment. 39 Now when the Pharisee who had invited him saw this, he said to himself, “If this man were a prophet, he would have known who and what sort of woman this is who is touching him, for she is a sinner.” 40 And Jesus answering said to him, “Simon, I have something to say to you.” And he answered, “Say it, Teacher.” 41 “A certain moneylender had two debtors. One owed five hundred denarii, and the other fifty. 42 When they could not pay, he canceled the debt of both. Now which of them will love him more?” 43 Simon answered, “The one, I suppose, for whom he canceled the larger debt.” And he said to him, “You have judged rightly.” 44 Then 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. 45 You gave me no kiss, but from the time I came in she has not ceased to kiss my feet. 46 You did not anoint my head with oil, but she has anointed my feet with ointment. 47 Therefore I tell you, her sins, which are many, are forgiven — for she loved much. But he who is forgiven little, loves little.” 48 And he said to her, “Your sins are forgiven.” 49 Then those who were at table with him began to say among themselves, “Who is this, who even forgives sins?” 50 And he said to the woman, “Your faith has saved you; go in peace.”
In this gospel passage, we discover two approaches to Jesus — two ways to view him, to think about him, two ways to approach him. And we’re also forced to ask ourselves which way we’re approaching Jesus. But this is a beautiful story from the life of Jesus, which I hope will compel all of us — Christian or not — to love him even more than we do right now. Two approaches to Jesus and how you’re approaching him. That’s where we’re headed today.
TWO APPROACHES TO JESUS
Beginning with two approaches to Jesus. The two approaches to Jesus are highlighted by the two people interacting with him in this story: Simon, the Pharisee, and the unnamed woman. Let’s look at Simon’s approach to Jesus first. We’re in verse thirty-six.
Luke 7:36 ESV
36 One of the Pharisees asked him to eat with him, and he went into the Pharisee’s house and reclined at table.
We’ll skip to verse thirty-nine, where in response to the woman’s approach to Jesus…
Luke 7:39 ESV
39 Now when the Pharisee who had invited him saw this, he said to himself, “If this man were a prophet, he would have known who and what sort of woman this is who is touching him, for she is a sinner.”
There’s more we’ll see about Simon’s approach to Jesus, but for now, let’s make a few observations. Let’s start with a positive observation: Simon invited Jesus to his house to have a meal. That’s a good thing! Simon’s going to take a beating here in a moment, but I don’t want to miss this positive observation. Unlike many of the Pharisees, who wanted nothing to do with Jesus, Simon — in quite a bold move — invites Jesus to his home for a meal.
Now — he hasn’t been the best host — as we’ll see in a minute — but there’s at least some curiosity on Simon’s part when it comes to Jesus. He’s intrigued. He’s not out simply to trap Jesus, as other Pharisees try to do. In fact, Simon had no idea that a woman, who becomes the center of his conversation with Jesus, would disrupt his meal. All that to say, many people have a similar curiosity about Jesus. They’re not completely turned off by him — as others are — but they’re not completely convinced either.
- This may be your son or daughter — they’re not antagonistic towards Jesus, but they’re not in love with him either.
- This may be your co-worker, your roommate, your sibling, your spouse — they’ll show up to church with you, talk about Jesus with you; the door isn’t shut, but it feels like it’s barely pried open.
- This may even be you.
But this seems to be where Simon’s at in his approach to Jesus. He’s curious, but not much more. Thus, when he sees Jesus’s reaction to the woman’s behavior, Simon thinks to himself, “If this guy was really a prophet, he wouldn’t let her touch him.” This tells us that Simon’s not even convinced that Jesus is a prophet, much less the Son of God and Savior of the world.
One has to wonder — though — why would Simon have invited Jesus to his house for a meal? Being a Pharisee, Simon was a well-educated individual. So maybe he had questions for Jesus about his ministry or something he’d heard Jesus teach. Maybe he wanted to test Jesus’ knowledge of the Bible. Who knows, but Simon — though curious — still has serious doubts about Jesus.
Now — let’s turn to the woman — and then we’ll let Jesus highlight the difference in both of their approaches to him. We’re in verse thirty-seven.
Luke 7:37–38 ESV
37 And behold, a woman of the city, who was a sinner, when she learned that he was reclining at table in the Pharisee’s house, brought an alabaster flask of ointment, 38 and standing behind him at his feet, weeping, she began to wet his feet with her tears and wiped them with the hair of her head and kissed his feet and anointed them with the ointment.
A few observations about her. First, Luke doesn’t come out and say it, but in describing her as a “woman of the city who was a sinner” — most likely he’s indicating that she was a prostitute. Again, we’re not certain about this, but that’s what many scholars believe Luke is describing.
Second, she wasn’t invited to the meal, but she barged in anyway. Something helpful to know about meals in this culture is that homes had more of an open floor plan than many homes today. Doors were often left open to let air in, and meals would take place in what would’ve felt more like a public space than in a private home. So it wasn’t uncommon for neighbors or others to be uninvited participants in meals like this.
But what would’ve been unusual was for a prostitute to show up. As you can tell from Simon’s remarks about her, prostitutes were not favorably looked upon. Yet this woman approaches Jesus from behind and begins to weep. And the word Luke uses is sometimes translated as rain. So this was no insignificant shedding of tears — she’s crying so much that Jesus’s feet, which would’ve been behind him because of how they sat around the table — she was crying so heavily that his feet got wet because of her tears. And knowing she needed to do something, she dried his feet with her hair, then kissed them and anointed them with the ointment from the alabaster flask that was hung around her neck.
These flasks were fairly common in the culture of the day. Women, in general, would wear them — but prostitutes in particular wore them as a way to allure men. And when she took down her hair to dry Jesus’ feet — well, doing so was considered so inappropriate that a man could divorce his wife for behaving in such a way. A woman with her hair down, culturally, meant that she was a loose woman — a promiscuous woman — she’s the kind of woman you didn’t want your husband being around. And, in the culture of the day — a culture much different than our own — a woman’s honor was based on her reputation for sexual modesty and chastity, and any appearance of sexual indecency would bring dishonor to her husband. You may disagree with that kind of thinking — but that was the reality of the day in which she lived. And she knew all of this, and yet she let down her hair to dry Jesus’s feet, which were wet with her tears.
And then she takes that flask of ointment — an item of value — an item that, in many ways, was her identity, for she’d given her life to prostitution — and what does she do with it? She uses it to anoint Jesus’ feet. To anoint something or someone is to set them apart as holy and sacred. And she anoints Jesus with her most valuable possession. It’s like she’s giving herself to him as she realizes that this ointment — as well as herself — can be used for a better purpose.
Later, Jesus compares the two — Simon and the woman — when…
Luke 7:44–46 ESV
44 Then 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. 45 You gave me no kiss, but from the time I came in she has not ceased to kiss my feet. 46 You did not anoint my head with oil, but she has anointed my feet with ointment.
Simon didn’t give Jesus the culturally appropriate and common courtesy of offering him water to wash his feet upon entering Simon’s house. The woman washed his feet with her tears and hair. Simon didn’t greet Jesus warmly — that’s the kiss being referred to. The woman, however, kissed Jesus’s feet. Simon didn’t anoint Jesus’ head with oil. She anointed Jesus’s feet with her expensive ointment.
Two vastly different approaches to Jesus.
WHAT THE WOMAN KNOWS THAT SIMON DOESN’T
Those are the facts that Luke records for us as he describes this moment in Jesus’ life. And now we turn to the reason why there’s such a difference in their two approaches to Jesus. Why do Simon and the woman respond to Jesus the way they do — why are their responses to him so drastically different? We’re in verse forty — right after Simon thought to himself, “I guess Jesus isn’t a prophet, for he doesn’t even know what kind of woman she is.”
Luke 7:40–43 ESV
40 And Jesus answering said to him, “Simon, I have something to say to you.” And he answered, “Say it, Teacher.” 41 “A certain moneylender had two debtors. One owed five hundred denarii, and the other fifty. 42 When they could not pay, he canceled the debt of both. Now which of them will love him more?” 43 Simon answered, “The one, I suppose, for whom he canceled the larger debt.” And he said to him, “You have judged rightly.”
Someone’s said, “Anytime Jesus says, ‘I have something to tell you’, you better run. He’s about to throw you a spiritual grenade.” And that’s what Jesus does when he tells Simon this parable — a parable’s a short story meant to teach a truth — and the point of this parable is pretty straightforward.
There are two people who both owe a debt to their lender. Neither can pay back their debt. And, in Jesus’ day, that meant you went to prison until you could pay your debt off. But being in prison meant you weren’t making any money, which meant you still couldn’t pay your debt off — so you stayed in prison. You get the idea. If you can’t pay your debt — essentially — you go to prison for life.
So there are two people in debt. Since denarii mean nothing to us, we’ll keep this simple. One person owes two years’ worth of pay while the other owes two months’ worth of pay. Both are large amounts — but one is ten times larger. But — again — the point is that they both owe money and neither can pay it back. Don’t focus on the difference in the debt they owe — focus on the fact that neither can pay back the debt they owe.
After setting the scenario, Jesus says, “Then the lender cancels both of their debts.” So both debts are forgiven. Both people were facing life in prison, and now they’re both debt-free.
So Jesus asks Simon, “Simon, of the two, who would love the lender more after having their debt forgiven? Who’d be rejoicing more? Who’d be more relieved?” That’s Jesus pulling the pin on the spiritual grenade as he hands it to Simon. And what does Simon say? He says, “I suppose the one who had the bigger debt.” And Jesus tells him he’s correct.
And the grenade goes off in verses we looked at earlier.
Luke 7:44–46 ESV
44 Then 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. 45 You gave me no kiss, but from the time I came in she has not ceased to kiss my feet. 46 You did not anoint my head with oil, but she has anointed my feet with ointment.
That’s where we stopped earlier, but look at what Jesus says next. He says…
Luke 7:47 ESV
47 Therefore I tell you, her sins, which are many, are forgiven — for she loved much. But he who is forgiven little, loves little.”
Do you see what Jesus did? He tells Simon that he and the woman are the two debtors in the parable. Essentially, Jesus says to Simon, “Simon, you’re in the same boat that she’s in. You’re unable to make good on your sin debt. Yes, yes, I know. It’s a much smaller sin debt than hers, but it’s still a debt you can’t pay. You’re just as condemned as she is.”
And I know how offensive this can be to our ears. But if you don’t understand this view of sin — you really don’t understand the gospel. For no matter the sin we’ve committed — none of us can pay back the debt we owe. Even the most moral among us have a sin debt we can’t repay. Your pile of debt may be nowhere near as big as others — but it’s still too much for you to pay back. Even with an eternity before us — there’s still not enough time for any of us to repay our sin debt to God.
And, honestly, not understanding this is the cause of much anxiety in people’s lives — not all anxiety — but much of it’s caused by living under the guilt of the sin debt you owe. A lot of the anger you experience is because you’re mad that God’s not saying “paid in full” because of what you’ve done for him. I wonder how you’re responding to the news that — because of your sin — you owe a debt to God that you can’t repay?
After his short illustration, Jesus then points out to Simon the difference between how both he and the woman have responded to Jesus. How they’ve both approached him. “Simon, she’s responded by showing me love. She’s adored me. She washed my feet with her tears and wiped them dry with her hair when you didn’t even show me the courtesy of basic hospitality by offering me water to wash my feet. You didn’t give me a kiss of welcome. You showed me no such courtesy while she hasn’t stopped kissing my feet. You didn’t anoint my head with oil when I came into your home, but she’s anointed my feet. Simon, your own words condemn you. For everything she’s done shows that she recognizes that her sins — which are many — can be forgiven — not because she can pay back her debt, but because she’s found the one who can. While your response to me, well, your response suggests that you still think you can pay back God for your sin debt.”
CONCLUSION: HOW ARE YOU APPROACHING JESUS?
So how are you approaching Jesus? Simon and the woman both wanted to see Jesus. Both wanted to be in his presence. Both wanted to be near him. And they both heard his words about sin and forgiveness.
She’s transformed while Simon isn’t. She shows obvious love and joy — because of Jesus — while Simon — at best — keeps Jesus at arm’s length. And look at how the story ends. We’re in verse forty-eight.
Luke 7:48–50 ESV
48 And he (Jesus) said to her, “Your sins are forgiven.” 49 Then those who were at table with him began to say among themselves, “Who is this, who even forgives sins?” 50 And he said to the woman, “Your faith has saved you; go in peace.”
Her sins are forgiven. But what about Simon’s sins? Luke doesn’t tell us, does he? Though he doesn’t tell us, it seems like Luke wants us to conclude that her sins were forgiven while Simon’s weren’t. So — again — how are you approaching Jesus?
Simon kept Jesus at arm’s length. He didn’t want Jesus to get too close to him. He definitely didn’t want Jesus to be someone to whom he owed a debt of any kind. He’s willing to listen to Jesus, yes. Have a conversation with him, sure. For many people — when it comes to Jesus — it’s OK for your mind to be involved, but — like Simon — he’s never going to have your heart.
The woman, on the other hand, gave all of herself to Jesus. Her mind, yes. But even more than her mind. She wasn’t going to keep Jesus at arm’s length. She not only wanted Jesus close, but she went to him to get close to him. And she knew that, if there’s anyone in the world to owe a debt to, Jesus is the best option. For he’s the one who forgives us of our debts.
But don’t miss this: they both want Jesus in their life, just in entirely different ways. Thus the warning to all of us is that you can be a very religious person, come to church, serve, be in a Life Group, support a church financially, read your Bible and pray — do all sorts of religious activities — all while keeping Jesus at arm’s length. You can be someone who doesn’t mind hearing what Jesus has to say; you may even say you believe what he’s said, but your relationship with him is solely intellectual. You agree with your mind, but you don’t love him with your heart.
For others it’s like this: You’re good with Jesus as long as you’re in control of the relationship. That was Simon — he was good with Jesus as long as he was the one asking the questions. But once Jesus started asking the questions — well — that was enough for Simon. Who asks the questions in your relationship with Jesus? Are you asking him all the questions, or is he asking you questions? Who’s changing who in the relationship? When you find yourself in a disagreement with Jesus, who’s right? Now we all know the answer is supposed to be “Jesus,” but is that how you’re living?
One pastor has described it this way. “Simon is approaching Jesus the way many…people do. Simon’s interviewing Jesus. In other words, Simon is sitting down and saying, “Jesus, I’ve been looking at you, and you do miracles. That’s very impressive. I’ve heard your teaching, and it’s remarkable. I’m trying to figure out right now whether it would be advantageous to me to have you in my life as a shepherd and guide. So would you fill out these forms in triplicate, please?” In other words, he’s in control. Jesus is the applicant. He’s interviewing Jesus to see what he thinks.”
I wonder if this describes any of our relationships with Jesus? Where you’ve asked him to fill out an application to be the god of your life, where you’re interviewing him — and probably a few other options — to see which god is the best option for you.
Friends know that Jesus can’t be approached this way. He’s not someone you interview — he’s the one who’s asking all of us to receive forgiveness. To respond to the gift he’s offered by giving his life on a cross to pay our sin debt in full. And for those who’ve been forgiven — just like the woman — for those who really see that their sin — no matter how small or insignificant or “not as bad as those other people” they think their sin is — just like the woman, all who truly respond to Jesus in faith — believing in him with their mind, yes, but with their whole being — see that they’ve been forgiven of a debt that — not only could they not repay — but the consequence of defaulting was an eternity in the prison of hell.
And, like the woman, the entire direction of your life will be changed. She knew that Jesus couldn’t be an add-on to her life. It was all or nothing. All of her tears or none of them. All of the ointment or none of it. All of her heart, mind, soul, and body — or none of her. There’s no getting Jesus partially into your life — where it’s like, “Jesus, I’ll take a little bit of you, but all of you would be too much. So how about we have a relationship where I still get some personal space?” To which Jesus says, “If personal space is what you want more than me, then you can have it without me.”
It’s not enough to just invite him over to your house for a meal. He’ll ask you why you didn’t offer him water for his feet, why you didn’t greet him with a kiss, or why you didn’t anoint his head with oil. And it’s not enough to invite Jesus into your heart — as we Christians like to say. He’ll ask you why you didn’t offer him that part of yourself that you think you can stay in control of. And when Jesus isn’t what you value and love most, like Simon, his questions will really get to you. They’ll irritate you. Because you’ll come to realize that Jesus won’t let you treat him like you treat everyone else because he’s completely different than the rest of us. He’s either your Savior and Lord, the Son of God and Creator of all things, the one whom every knee will bow before one day — or he’s — as C.S. Lewis said, “A liar or a lunatic.” Liar, lunatic, or Lord — those are your options.
Those who believe he’s a liar or a lunatic respond to him like Simon — he’s welcome to come over and hang out as long as he doesn’t expect you to go out of your way or anything. But those who believe that he’s Lord respond to him like the woman — they give Jesus all of who they are, anointing him with the ointment of their entire lives.
How are you responding to Jesus? Let’s pray.
PRAYER
Father in Heaven, you are holy, majestic, loving, and kind. You are the One who will judge every single one of us, and your judgment will be just. This should stir in us a holy fear because of our sin — no matter how insignificant we may consider our sin to be — we owe a debt to you that we can’t repay. And the consequence — the deserved consequence — is an eternity in hell.
Spirit of God, you are the Spirit who gives life to our spirits. You open spiritually blind eyes and deaf ears, and give new life to spiritually dead hearts so that we might respond to the Good News that God saves sinners. And that all who come to Jesus repenting of their sins and believing in him will be forgiven. For though the wages of sin is death — the free gift of God is eternal life. And this free gift is possible because Jesus paid our sin debt in full on the cross.
To you, Jesus, the payer of our sin debt and the One to whom we now owe our lives, we first thank you for your love for us. No mere lip service, your love is one of action. And, in response to being forgiven, our love for you is now one of action. Of anointing you with our lives as we live for you. Serving you. Sharing with others the news of your love. A life of loving you.
Father, Son, and Spirit — for any who came here today approaching Jesus like Simon once did — we ask that you would help them to see the better approach. The humble approach. The “I won’t hold anything back from you” approach that the woman displayed. For that is the approach of those who realize their need to be forgiven — who are then those whom you forgive. Jesus, forgive many who approach you today. And we pray all of this in your name. Amen.
BENEDICTION (Prayer teams available)
In response to who Jesus is and all that he’s done for you, may you go anointing him with your life. Amen.
God loves you. I love you. You are sent.