What does Luke 7:44 mean?
After a sinful woman interrupts a banquet at the home of Simon the Pharisee to wash Jesus' feet and anoint them with perfume, Jesus tells a parable. His story demonstrates that loving God, which is the most important of all the laws the Pharisees claimed to follow, is most easily fulfilled by those who understand the weight of the sins of which God has forgiven them (Luke 7:36–43). Now, Jesus closes the interaction by comparing the woman's extravagant display of honor to Simon's bare minimum attentions.As in the case of the woman with the issue of blood (Luke 8:43–48), Jesus stops everything to affirm the actions of a desperate woman. In the home of Simon the Pharisee—a man who lives every day in incessant rituals meant to protect him from sin—Jesus presents a sinful woman as an example to follow. In so doing, Jesus publicly announces that her loving actions are a sign that God has already forgiven her. This implies that Simon, the other guests, and all the onlookers should no longer consider her a sinner when God has made her whole, and ought to learn from her example.
Scholars debate whether Simon was culturally obligated to give Jesus water for His feet, kiss Him, and anoint His head with oil (Luke 7:45–46). Considering the echo of "the city" in verses 11 and 37—the Greek is the same, even though English translations differ—this is could still be the town of Nain, where Jesus raised the dead man (Luke 7:14–15). If so, Jesus has been there for enough time for John's disciples to visit him near the Dead Sea and return, and Jesus has spent this time healing the people and expelling demons (Luke 7:21–22). Even if this is not Nain, Simon knows what Jesus has done (Luke 7:17).
Simon is interested enough in Jesus to invite Him to his home, and respects Jesus enough to give a banquet; the reclining diners describes a formal meal (Luke 7:36). If the courtesies Jesus lists, such as water for feet, kiss of greeting, and oil for His head, are cultural standards, Simon has disrespected Jesus. Considering the importance of hospitality and honor in that time and place, that's unlikely.
It's more likely that Jesus is noting the things Simon could have done if he loved and honored Jesus. Simon invited Jesus to a culturally appropriate meal and gave a culturally sufficient welcome. The woman Simon silently shamed (Luke 7:39) has shamed Simon by demonstrating what it means to truly honor Jesus.