What does Luke 7:43 mean?

A Pharisee named Simon had his banquet interrupted by a woman with an immoral reputation. She started washing his guest's feet with her tears and hair and anointing them with perfume. The guest was thought to be a prophet of some kind but made no move to dismiss the woman. According to Simon's way of thinking, if the guest doesn't even know what kind of woman this is, He must not be much of a prophet (Luke 7:36–39).

The guest, of course, is Jesus. He knows exactly who the woman is and what she has done (Luke 7:47). He also knows why the woman is acting this way. At some point, she heard Jesus' message and accepted forgiveness for those many sins. In response, she wants to extravagantly show love and gratitude. A banquet, where the door is open to those who want to listen in on the conversation, is much more convenient than trying to push through the crowds that follow Jesus wherever He goes.

Simon doesn't see things this way, of course. Rather than being confrontational, Jesus tells him a parable (Luke 7:40–42). Two men owe a moneylender. One man owes two months' worth of wages while the other owes two years' worth. The moneylender forgives both debts. Jesus asks Simon to deduce which debtor will love the moneylender more.

Roman culture relied on the patronage system. A wealthy and/or powerful man would do favors for those who needed help, often by loaning money. The client would in turn do the bidding of the patron. The system worked on honor and trust. Jesus, however, adds another element: sacrificial love that wants the best for another. Simon has likely never considered that a client would love a patron. And yet, the Mosaic law, which Simon is devoted to, says, "You shall love the LORD your God with all your heart and with all your soul and with all your might" (Deuteronomy 6:5). Simon's perspective doesn't allow for the idea that a sinful woman could obey the most important part of the Law better than a Pharisee.

Simon gives a half-hearted response. He may be grudgingly conceding the point. Or, perhaps rabbinical training, which values vague answers, is kicking in. Jesus approves as far as it goes: Simon correctly judged the human response to charity and forgiveness. However, he misjudged God's eagerness to give charity and forgiveness.