Please understand that this is not the same event that took place in Bethany, on the hill east of Jerusalem close to the Crucifixion. Luke places this in the context of working in Galilee some time earlier, and the details are different enough that we can’t collate the two. It’s not hard to imagine how people would react similarly to Jesus’ ministry, particularly if they heard someone had done something they wanted to mimic. Equally, it shouldn’t surprise us that Jesus would repeat some teachings in different contexts.
We can’t be sure of the exact details, but this passage makes very little sense unless the host who invited Jesus to dine was quite wealthy and prominent. Further, the man had taken on some distinctly Roman habits.
The dining room was equipped with a large central table. There were either Roman style couches raised off the floor, or a raised central platform with Hebrew style pads around a low table. Either way, the idea was to recline on the left side at an angle to the table and eat with the right hand. Knees were typically bent some so that feet were then well away from the table. Further, there was a substantial shadowy space along the walls where servants could move and where the general public could slip in and hang out unobtrusively and watch this formal meal with important discussions taking place among notables. This was how the wealthy and powerful flaunted it for the curious.
It’s obvious from the context that Jesus was not the guest of honor here. The most likely point of inviting Him was Simon’s own curiosity, and perhaps to allow the other quests to query this controversial rabbi. The meal setting symbolized a non-hostile setting in Hebrew culture in particular, and it smacks of yet another attempt to manipulate Jesus.
No Jewish women were present; this was typically a men-only occasion. But this prostitute had no trouble slipping up behind Jesus and engaging in her bizarre ritual. To top it off, no self-respecting Pharisee would tolerate such physical contact in public, but she didn’t actually interrupt anything. You’ll notice no one shooed the woman away. So once this woman began her ministrations, Simon thought to himself that Jesus couldn’t be much of a prophet, tolerating this ultimate sinner among Jews.
Jesus asked if He could say something, and Simon as master of ceremonies at this lavish dinner invited Him to proceed. The parable of loans requires us to understand that debts between Jews were typically limited to kin, either by blood or marriage. They were very personal in nature, with none of the formal and legal provisions we expect today. The debtor didn’t owe some impersonal corporation, but his own kin. Failure to repay hurt everyone dependent on the creditor.
But while perhaps rare, it wasn’t unheard of for such debts to be forgiven. Who would be more grateful and more likely to try doing favors in return for the mercy, the one who owed two months’ wages, or the one who owed two years’ worth? When Simon responded with the obvious answer, Jesus sarcastically noted how wise he was.
This a delicious irony here in what Jesus said. A prostitute was a parody of good moral hospitality. Yet here this woman provided the most lavish hospitality to Jesus in place of Simon’s scandalous lack of it. The obvious implication is that Simon never saw himself much indebted to God for his sins. That’s what it means to be “self-righteous” as Simon clearly was. That perfume was obscenely expensive. This woman spared no expense in offering all she had for her sins, taking great risk to do so. She groveled extravagantly where Simon was frankly rude. She wasn’t trying to cultivate another client. She was a penitent worshiping Jesus whose ministry was a very loud call to repentance.
Jesus announced that her sins were forgiven regardless of how great and numerous they were. What was left unsaid is that Simon’s sins were not forgiven. Now the others at the table wondered who Jesus thought He was to announce forgiveness of sins, but the answer was in Jesus’ final words: Your commitment to seeking God’s favor is precisely what wins that favor. The depth from which you have to crawl to enter His Presence isn’t much of a factor, but nobody has a prior claim on God’s mercy.