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Throwing Caution to the Wind
Luke 7:36-50 (Matthew 26:6-13)

This morning we’ll be reading and studying in Luke, chapter 7, beginning at verse 36. It’s a remarkable encounter; one which teaches us the relationship between forgiveness and love, and which illustrates the contrast between arrogance and humility. It’s also a stirring example of faith and throwing caution to the wind.

In terms of the context, just a short time earlier, in Luke 5, Yeshua cleansed a leper, and instructed him to go and present himself to the priest and fulfill the Torah’s requirements “as a testimony to them” – testimony of cleansing, and of Yeshua’s power/Messiahship. We’re not told who that leper was, but there’s something fascinating that I want to point out to you before we dive into our passage this morning.

It seems that God likes to set things up like bookends. Parallel incidents that might otherwise might seem coincidental I take to be a sign of God’s fingerprint on the Scriptures. For example, the first three chapters of Genesis and the last three chapters of The Revelation have remarkably similar and parallel details. The beginning and the end of Yeshua’s earthly ministry had striking parallels. At the beginning and at the end He was alone, with no disciples around, being tested and overcoming temptation. At the beginning and at the end He went into the Temple and drove out the money changers and the merchants, and each time the Jewish leaders challenged His authority to do so.

And there’s another remarkable set of “bookends”. Near the beginning of Yeshua’s ministry and again near the end, He entered the homes of men named Simon, and each time a woman came to Him and anointed His feet with costly perfume. And each time, people took offense. Two different homes, two different Simons, two different women. But the parallel is remarkable.

Actually, it was this week’s parasha, M’tzora – “lepers” – that got me thinking about this. You see, the first of these homes belonged to a Pharisee named Simon, and the last belonged to a leper named Simon. Now, of course, Simon (or Shimon) was as common a name in Israel as “Jim” would be here in America. But the parallel is, I believe, God-intended. This morning we’re going to study the first of these encounters; the one that took place in the home of Simon the Pharisee.

Luke 7:36-50

Now one of the Pharisees was requesting Him to dine with him, and He entered the Pharisee’s house and reclined at the table.

It is completely understandable why one of the Pharisees, whose name we later learn is Simon, would want to have Yeshua come to his home for a meal. After all, this young carpenter-turned-rabbi had only recently begun His public ministry of teaching and healing, and already had cured a leper, restored a paralyzed man, cast out demons, healed a centurion’s servant who was about to die, and raised a man from the dead in Nain. Word on the street was that this rabbi had the power of God at work in Him, and yet was gentle and kind-hearted. Wouldn’t you be curious to meet someone like that?

What do we know about Pharisees? We know they were the pious, ultra-religious sect of Judaism. They were the machers – the big shots, fancying themselves the “gatekeepers” of Judaism. People held them in a mixture of reverence for their piety, and yet disdain because they could be harsh, hypocritical and egotistical. It would be unfair to say that all Pharisees were like that. Some were sincere in their faith, kind and genuinely devout. But because Yeshua so frequently took them to task for hypocrisy, we’ve come to view them rather cynically.

Many Pharisees were well-to-do. It is likely that Simon was among them. He hosts a meal at his home, and invites Yeshua to come. To have a rabbi come into your home was considered a high honor in ancient Israel. Yet, as we’ll find out in a few minutes, no honor was accorded Him. And that’s where our narrative continues. Yeshua has accepted the invitation, come into the home, and reclined at the table with the others.

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.

We aren’t told the name of this woman, but Luke gives us a bit of a description. She was regarded as a sinful person – in Greek, hamartolos. Most likely it was sin of a sexual nature. Very likely she was a prostitute, though there is a Greek word for that, and it isn’t used here. On the other hand, the word “prostitute” (pornei) only appears twice in the entire New Testament. “Sinner” could just be a more generic, perhaps even euphemistic expression.

But here’s the salient point: she heard Yeshua was in town, and dining at the home of this Pharisee, and she wasted no time going there to see Him. But what I want you to consider is the depth of her determination. She’s a woman with a reputation, so to speak, and she’s walking into a Pharisee’s home. She knows who she is, and she knows they know who she is. But she isn’t going to let anything stop her. She knowingly walks into an embarrassing situation out of sheer determination to see the One about whom she had heard so much. This Rabbi isn’t like the others. This One doesn’t point fingers. This One welcomes sinful people to come to Him, and in the process, they leave their sin behind! So what’s a little embarrassment in exchange for that kind of opportunity? She threw caution to the wind.

That is precisely the kind of courage and determination that pleases God.

Her faith is revealed in her actions. She comes despite the humiliation, and she doesn’t show up empty-handed. She has with her an alabaster vial of ointment – the Greek word for it is muron, from which we get the word myhrr. And at one point she is overcome with emotion and begins weeping heavily.

Now Yeshua and Simon the Pharisee (and presumably others) weren’t just sitting there, eating. No doubt they were discussing the Torah and the Prophets and the things of God. There is a rabbinical saying (Pirke Avot 3:3), if three eat at a table and do not speak words of Torah, it is as if they have eaten the meat of idolatrous sacrifices. Perhaps as Yeshua spoke about the Kingdom of God, explaining God’s Word, God’s ways, and God’s mercy, the woman broke down. Is it possible that mercy was something with which she had very little personal experience? The Greek construction of this sentence suggests she was weeping very deeply, perhaps uncontrollably.

Luke says, 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. Those were not wasted tears. But perhaps she’s embarrassed that her tears have fallen on Him. And so she kneels down and uses her hair to wipe His feet. What we are seeing is an act of great humility and faith. Assuming this is the first time this woman has seen Messiah Yeshua, she can only trust that He is as kind and merciful as the reports she has heard, and that she will not be rebuked by Him. Yeshua’s own words come to mind, Blessed are those who have not seen and yet believed. As we will see in a few minutes, her courageous act and her faith will be greatly rewarded.

But in contrast to this woman’s adoration, Yeshua is disdained by His host.

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.”

We can glean from this that on account of Yeshua’s many miracles, people were already heralding Him as a prophet. And that He was… though much, much more. But the Pharisee is indignant. He thinks to himself “Is this guy clueless? Doesn’t he know who and what this woman is that he’s letting touch him? Yeah, some prophet!”

How did Luke, writing this narrative of the life of Yeshua, know what Simon the Pharisee had been thinking? Now remember that in the opening words of this Gospel, Luke says that he had thoroughly investigated all the stories that had been handed down to them. So there are two possibilities here. Either Yeshua revealed that fact to the disciples who were there with Him that day, and they confirmed it, or else – and this would be very cool – Simon the Pharisee eventually became a disciple himself, and admitted to Luke what he had been thinking.

But for the moment, the Pharisee has only contempt in his heart; contempt for the woman for her sinful lifestyle (and who knows what series of misfortunes may have led her to such a life?), and contempt for Yeshua Himself, whom he presumes doesn’t know who this woman is. Simon didn’t verbalize his thoughts, but then again, he didn’t need to. It’s possible that he had a look of disgust on his face and that gave it away. But then again, consider that the guest in his home was the One through whom the universe was created. Messiah knows all things. And now He addresses His host.

And Yeshua answered him, “Simon, I have something to say to you.” And he replied, “Say it, Teacher.” “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.”

Indeed, a denarius was a day’s pay; so fifty denarii would be the equivalent of a month and a half’s wages. That’s still a pretty hefty sum of money. But five hundred denarii? That was the equivalent of a year and half’s wages!

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.”

Notice that Yeshua doesn’t attempt to whitewash the fact of this woman’s sin. Her sins, He acknowledges, are many. By comparison, Shimon the Pharisee has lived a life of religious devotion. Yet according to Yeshua, the greater sin between the Pharisee and the prostitute was the absence of love. Reckoning himself righteous, not particularly needing forgiveness, the Pharisee lacked mercy, and completely missed the significance of the One sitting right there at his table.

Hospitality in the ancient world, and especially in the Ancient Near East, was a sacred responsibility. Even today, to be invited to a Jewish home and not to be offered something to eat and drink is a sign of disrespect. In ancient Israel, when you invited someone to your home, it was customary to provide water for your guest to wash their dusty, tired feet. It was customary to welcome them into your home with a kiss. If you had sufficient means it was customary to anoint their head with a little oil. Simon had done none of those things for Messiah. Inviting Him to his home seems to have been an act of condescension, as though he was doing Yeshua a favor, and so he had dispensed with the usual politeness.

You see, it wasn’t just Simon’s lack of love compared to the woman generally that earned him the rebuke. It was his lack of love for Yeshua – this is all about Him. And we must not miss that. The extent to which you either love Him and give Him your very best, or treat Him with indifference, will be the determining factor in the disposition of how you spend eternity!

When was the last time you were on your knees before Him? Kneeling has become almost foreign to our culture. It is a sign of submission, and can also be a posture of adoration. If a billion followers of Islam can bow down 5 times per day, misguided as they are, certainly we ought to gladly bow before the Lord God of Israel and Messiah Yeshua the Son of God.

Messiah tells Simon the Pharisee that the woman’s many sins, in view of her love for and faith in Him, are forgiven. And now Yeshua turns to the woman directly and declares it.

Then He said to her, “Your sins have been forgiven.” 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 forgiven sinner comes away from this encounter joyful and with a clean slate and a fresh start. The self-righteous come away from this encounter critical of Yeshua and even more hard-hearted. And that is the nature of things with Messiah. He is the “Stone of stumbling” and the “Rock of offense” to the self-satisfied. But to the humble, He is the Fountain of Living Water. Yeshua the Messiah is the most pivotal individual in all of human history. How we approach Him is the single most important decision each one of us will make in this life.

Let me close with these thoughts:

This encounter perfectly illustrates the difference between casual curiosity (the Pharisee) and sheer determination (the sinner). A woman with a reputation knowingly risks embarrassment by coming into a pious Pharisee’s home; just like Zaccheus, a hated tax-collector, scorned for being short, knowingly risked embarrassment by climbing up a tree – and for the very same reason: for just one opportunity to see Yeshua! And the outcome was the same! To Zaccheus it was said, “Today salvation has come to this home!” To the woman it was said, “Your faith has saved you!”

Seek out Yeshua at all costs! Don’t let anything stop you. Your eternal standing with God is far too important than to worry about what some people will think! And if you would learn from this forgiven woman, then where Messiah Yeshua is concerned, throw caution to the wind. Come to Him with reckless abandon.