Rejection vs Repentance
November 16, 2025
November 16, 2025
Luke 7:28-50 - Riley Boggs
The Christian life is a repenting life, from start to finish. To repent means to change your mind about something, and in the case of the Christian, it means to change your mind about sin. Instead of overlooking it, accepting it, or loving it, we begin to feel sorrowful about it, turn from it and hate it, and confess it the Lord. That’s what repentance is. When we first come to faith we repent and then the rest of our lives we repent, until one day, there is no need for repenting anymore because we will sin no more. The Christian life is a repenting life.
Not only is that true, but it’s also true that the devil hates when you repent. He wants to keep you from it. In C.S. Lewis’ The Screwtape Letters we get a picture as to why this is the case. For those who don’t know, The Screwtape Letters is a fiction book where Lewis creates a dialogue between a senior demon and his apprentice demon. It’s a book of imagined letters from the senior demon to his apprentice, discussing how he might draw a man away from God. For those who haven’t read it, I would highly encourage it. But the reason I bring it up is because in the letters they address the idea of repentance several times. And one thing that the senior demon often says is that we must keep the man from repenting of his sin. He says it’s good for him to feel guilty about and shame, and that might even help their case. But they must try their hardest to keep the man from true repentance.
In one of the letters the senior demon writes this to his apprentice. “The great thing is to prevent his doing anything. As long as he does not convert it into action, it does not matter how much he thinks about this new repentance. Let the little brute wallow in it. Let him, if he has any bent that way, write a book about it; that is often an excellent way of sterilizing the seeds which the Enemy plants in a human soul. Let him do anything but act. No amount of piety in his imagination and affections will harm us if we can keep it out of his will. As one of the humans said, active habits are strengthened by repetition, but passive ones are weakened. The more often he feels without acting, the less he will be able ever to act, and, in the long run, the less he will be able to feel (pages 66-67).”
Why is this the case? Why is repentance so dangerous to the enemy? Why do they want the man to feel all those feelings about his sin without actually repenting? The reason is because repentance is where freedom is found for the Christian. When we repent of our sin, when we acknowledge it, confess it to God, and receive forgiveness, we are set free from the shackles of our sin. And then, we are encouraged to follow closer to our Lord and to keep further from sin. On the other hand, if we feel guilt and shame about our sin, but choose to suppress those things rather than repent, we will find ourselves being bound by our sin, feel like we are distant from God, and sear our conscience to the point where sin no longer bothers us. The enemy knows all of this, and it’s why he wants you not to repent, which is exactly why we need to be a repenting people. We need to be sorrowful of our sin, quick to repent, and have great joy when we receive the forgiveness that God pours upon us.
In our text this morning, we get a comparison between 2 groups of people. Those who are rejecting and those who are repenting. The story goes back and forth and shows us multiples examples both sides. The comparison is made by Jesus himself, starting in verse 28. Jesus says, “I tell you, among those born of women none is greater than John. Yet the one who is the least in the kingdom of God is greater than he.” We looked at this verse last week and talked about how Jesus is saying that because John is going to die before He sees Jesus’ death, burial, and resurrection, all those who do see this stand in a greater place that John. They get to see the fullness of what Jesus’ accomplished, while John only had the promises to look to.
After that, Luke records how the people respond to what Jesus has just said. And He tells us that there are 2 groups, each responding differently. When the general listeners and tax collectors hear this, they declare God just. They had been baptized by John, showing that they believed what John had preached about the coming Messiah, and by declaring God just, they are showing that they believe what Jesus is saying. On the other hand, Luke tells us that the Pharisees and lawyers did not accept what Jesus was saying. Instead, they Luke reminds us that they had rejected what John had preached about and now, by denying this to be God’s plan, they are rejecting what Jesus is saying.
Jesus, seeing this, speaks about the pharisees and lawyers. He asks, “To what then shall I compare the people of this generation, and what are they like?” Then he gives an example of what they are like. And what he says is that they are like spoiled children who reject everything you suggest to them. He says they are like the child who pushes through their mountain of toys, looks up at their parents, and says, “I have nothing to play with!” He says that they are like the child who insist that they are simply going to die of boredom, and yet, everything you suggest to them gets shot down immediately. In other words, nothing satisfies them. That’s what I want you to see for our first point this morning.
1.) Those who reject Jesus will never be satisfied
Jesus continues on this and even shows them how they are like spoiled children. He says, starting in verse 33, “33 For John the Baptist has come eating no bread and drinking no wine, and you say, ‘He has a demon.’ 34 The Son of Man has come eating and drinking, and you say, ‘Look at him! A glutton and a drunkard, a friend of tax collectors and sinners!’ 35 Yet wisdom is justified by all her children.” In other words, nothing satisfies you! For them, John was too disciplined and stern, while Jesus was too indulgent and gentle, and so, neither will do. This truth isn’t certainly not restricted to these people, in this place, in this time. In fact, I would argue that this has been, and forever will be, true of all people who reject Jesus, they will never be satisfied.
To be satisfied means to be pleased or to be content. It means that we don’t need more, we have enough. And in this case specifically, we are saying that Jesus doesn’t have to be anything less or anything more for us to be satisfied with Him. When we say we are satisfied with Christ, we are saying that He doesn’t have prove Himself anymore. We are content with who He is, what He has done, what He has promised, and all the rest. That’s where the tax collectors, the “worse sinners” were. They accepted what Jesus was saying, they trusted His Words, and they declared God just. But the Pharisees and lawyers, the ones who really knew what’s up apparently, needed more. John was too this, and Jesus is too that.
I’m sure you’ve heard this from unbelievers. They say, “I would believe in Jesus if…” They say, “I would believe in Jesus if there was indisputable evidence” or “I would believe in Jesus if He showed up in front of me.” In other words they are saying, “I would believe in Jesus if He met my demands on what I need in order to believe something. Until I’m satisfied, I can’t believe.” But see the issue is that there will never be enough for them, they can’t be satisfied. My chief example of this being true are the Pharisees who are standing right here in front of the Lord Himself. They have seen Him heal people, forgive people sins, and have ever listened to Him show from the prophets that He is the Messiah, and yet, they deny Him.
And for those unbelievers who do make those kinds of claims, what you’ll find is that nothing satisfies them. They spend their life on a never-ending search to fill a void that can’t be filled by the things of this world. At times that feeling is dulled a bit, in other times it feels all-consuming, but at all times it is present. Ask someone what they want most in life and they will tell you things like, “Happiness, purpose, or pleasure.” Then ask them if they have it, and if they don’t, ask how will they ever get it. Their answer will likely be future time where they foresee all of those things finally being their reality. But you all know as well as I do, once they get there, that future time will still feel a bit further down the road.
What a person in this situation needs is not different circumstances. They need something, or someone, that grants satisfaction despite circumstance. They need to repent of their sin and to trust in Christ. Because it is in Him and Him alone that there can be joy in sorrow and peace in times of trouble. It is in Him alone that there can be contentment now and hope for tomorrow. It is in Christ alone that a sinner can be satisfaction.
In the second story of our text, we see a woman who understood this truth. Starting in verse 36 we read that one of the Pharisees, whose name was Simon, who just to be clear is not Simon the discipline who Jesus renamed Peter. This is a Pharisee whose name was also Simon, and the man who invited Jesus to his house to eat a meal. Jesus, as we see, accepted the invitation, went to his house, and reclined at the table to eat. And as was custom at these kinds of meals, people would often come and go throughout the meal. And we read in verse 37 that a woman, who Luke identifies as a sinner, which likely meant she was a prostitute, heard that Jesus was eating at Simon’s house. And when she heard this, she decided to go.
So she heads to Simon’s house, bringing an alabaster flask of ointment. She gets to the house, goes to Jesus, and begins to weep. She weeps and wets Jesus’ feet with her tears. She uses her hair to wipe his feet, kisses them, and anoints them with oil. She’s honoring Jesus. Simon sees this happening and thinks to himself, “If Jesus really was a prophet, if He knew who this lady was, there is no way He would let this happen. If He knew what she has done like I do, He wouldn’t allow this to continue.” But what Simon doesn’t realize is that Jesus knows exactly who this woman is, and He knows exactly what she has done, and yet, He gladly allowed this. Why? Our second point this morning.
2.) Jesus knows our sin and still forgives us
Simon was sure that Jesus was just ignorant as to who this lady was and what she had done. He couldn’t conceive of a situation where He knew all of that and allowed such a thing to happen. But Simon was wrong. This is another one of those contrasts that I was talking about earlier, Simon and the sinful woman. One understanding the weight of their sin and the grace found in Jesus, and one hardened by his own sin and blinded by his pride.
Jesus perceived what Simon was thinking and says, “Simon, I have something to say to you.” And begins to tell him a story. You can see the story in verse 41. He says, “A certain moneylender had two debtors. One owed five hundred denarii, and the other fifty. 42 When they could not pay, he cancelled the debt of both.” And then He asks Simon, “which of them will love him more?” Simon responds and says, “The one, I suppose, for whom he cancelled the larger debt.” Jesus says, “You have judge rightly.” But while Simon judge rightly in that example, he was yet to see why Jesus is saying this.
Then, Jesus turns to the woman and asks 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.” And then, He turned to her, and said, “Your sins are forgiven.” Everyone at the table began to ask, “Who is this, who even forgives sins?” And so, He turns to her one last time and says to her, “Your faith has saved you; go in peace.”
Think of the contrast between these two people. On one hand, you have a woman who is broken over her sin. She is sorrowful for what she has done. And yet, she knows that if she repents of her sin and comes to Jesus, she can be forgiven. I’m sure it wasn’t easy for her to walk in that house of Pharisees. I’m sure she felt the shame pressing down on her as people watched her walk to Jesus. And yet, she did it because she knew that she must show honor to the one who can forgive her of her sins, and so she does. On the other hand, you have a man who felt above things kinds of these. We don’t know why Simon invited Jesus to his home to eat, but we do know that he did not show Him honor at his coming. And not only that, but he was appalled at this woman giving him the honor that he neglected to.
When it comes to our own sin, we have a decision to make. We can choose to respond like Simon the Pharisee, or we can choose to respond like the sinful woman. Let me show you what this might look like. Let’s say one day you falter and find yourself acting or thinking in sinful ways. In a way that you thought you would never sin, and yet, you did. In that moment, you might feel some regret about what you have done, but you continue on your day. However, as your day goes on, what you did keeps coming to your mind over and over again. And now that regret has turned to guilt and that guilt is starting to turn into shame. It feels like it’s hanging over you the rest of the day, all day, until finally you get home and sit down. And as you sit there, you know what you should do, but you’re having a hard time doing it. You want to confess what you did to the Lord, and you want to repent, but you feel like God is so disappointed in what you’ve done that you can’t. You think about how no one else knows what has happened but yourself and God, and He can’t believe you would do that. He doesn’t want to be near you, so you won’t even bother. That is exactly how Simon acted. Except when we see Him do this, it looks arrogant. But for some reason when we do it to ourselves it feels humble and deserving. Well, it’s not.
In times like this, we need to respond like this sinful woman. When the sin has been hanging over us all day, and we get home and sit down, we confidently go to God in prayer. We are truly broken over our sin, so with tear-filed eyes, we confess our sin to Him. We ask that He comfort us with His Spirit, that He strengthen our fight against sin, that He increase our love for Him, and that He help us to walk in the forgiveness bought by the blood of Jesus. Though it may feel difficult to walk into the presence of our Lord, we do it because we know who He is. He is the friend of sinners, who isn’t ignorant of our sin, but knows the depths of it better than we do, and still chooses to forgive us.
It’s not that Jesus didn’t know who this woman was or what she had done. Jesus knew everything there was to know about this woman and chose to forgive her still. The same is true of each and every person here today. No matter who you are, God knows everything there is to know about you. And He has said that if you come to Him and repent of your sins, you will be forgiven. And once we do this, there is a right response. That response is one of worship, which is our final point this morning.
3.) True repentance leads to worship
One of the things on the infinite list of why Shelby is the greatest wife ever is how quick she is to forgive me. When I wrong her or treat her in a way she shouldn’t be treated, the moment I ask for forgiveness, she forgives me. Even when I do something that I said I wouldn’t do again, she forgives me. And what happens is that every time she is quick to forgive me, my love for her grows. I find myself wanting to show her more honor and love her better. I think about how gracious she’s been to me, and it makes me want to serve her well. That same dynamic is true when it comes to our relationship with God, except infinitely more. As we come to Him with our sin, and as He is faithful to forgive us, it will lead us to love Him more and more And in the case of God, and not our spouse, that means it leads us to worship Him.
Jesus points this very thing out in the example He tells Simon about the two people who have their debt cancelled. The simple fact that He is trying to remind Simon of is that the one who is forgiven much, who has more debt cancelled, loves more. Why? Because they realize the great cost at which they have been forgiven. This is why the woman, who had sinned greatly, falls at the feet of her Lord to honor and worship Him. Her repentance has led her to worship because when as she repents, she is forgiven. And it’s also why Simon, who has refused to repent, withholds the honor and worship that Jesus deserves.
Us humans are good at finding loopholes. When it’s to our benefit, we are tempted to walk in the grey areas of life. The best example of this is when it comes to taxes. We’ll pay our fair, or unfair, share, but only after making sure there is not a single loophole left untested. We say things like, “Well technically I did mention my job while we played golf that day.” Anything we can do to make it a bit easier on us, right? Well, there is no loophole when it comes to repentance. There is no amount of feeling bad about what you’ve done that equates to repentance. There is no amount sorrow or tears that bring it about. Those things in and of themselves aren’t repentance. Repentance takes place when our brokenness from our sin leads us to Jesus, whereby we confess our sin, and are forgiven. The reason that this young woman was forgiven is not because she wept, it was because she believed that Jesus could save her. How do we know that? Because Jesus tells her that her faith has saved her, not her sorrow, not her tears, her faith. The same is true of us.
We can’t wallow in self-pity and think that is what repentance is. Because what will happen is that as you continue to feel worse and worse, refusing to repent, you will find yourself without peace and not actually worshipping God. That’s a tell-tell sign that you need to confess to the Lord and repent, when you aren’t worshipping. When you feel like you’re good to go, with nothing to take to the Lord. But the beauty is that when you repent, when you receive the forgiveness Christ bought for you, worship begins to flow out. You have a heart of thanksgiving and of joy, and so you sing and pray and work unto the glory of God, the one who cancelled your debt.
This morning, from this text, I want to remind us that we are to live a life of repentance. A life that acknowledges our failures and ours sins. A life not only sees them for what they are, but a life that then takes them to the Lord, trusting that He is who He says He is. Trusting that He knows our sin, all of it, and still forgives us. Trusting that He alone can satisfy us, nothing in this world. And I promise that as you do that, you will find yourself having every reason to praise the Lord. Amen.