Summary: God absorbs a debtor’s default.
Read Luke 7.36-50. Pray.
So bad people need big forgiveness; as a result, when they meet Jesus, they love him much. Better people need less forgiveness, and so love little.
The woman was bad, “a woman of the city,” “a sinner.” To state it crassly, a streetwalker or prostitute. She needed big forgiveness, which she finds in Jesus; so she loves him greatly. Simon, on the other hand, was religious, an upstanding and respectable citizen, moral, a Bible student and theological expert, a elder in the Old Testament church. He has walked far on the road to godliness. With less sins to forgive, he is (understandably) less enamored with Jesus.
The parable of the two debtors seems to teach that. In the parable, Jesus is the moneylender; the woman owes five hundred denarii, Simon only fifty. When the debt of both is cancelled, the woman’s larger debt creates within in heart greater love, which explains her strange behavior.
Simon (on the other hand) is a Pharisee, and while we may feel negative connotations about members of that sect of Judaism, Pharisees were respected and honored in their towns. Simon’s invitation to dinner was a gift, a sign of admiration that Jesus rarely received. Like the mayor of Cincinnati inviting you to dinner, Simon says, “I am interested in what this rabbi teaches,” and everyone in town knew of it.
So Jesus enters Simon’s house and takes “his place at the table.” The implication, I think, is that this is a public, or at least semi-public event: one of the town leaders receives an itinerant rabbi. I would guess, though it is not said, that other dignitaries attend (like Turkey trip). Jesus takes his place, the one assigned, the place which all the other guests can see and easily point their questions toward.
They did not eat at chairs, but long couches, reclining, probably with one or both elbows resting on a pillow. Here is an artist’s picture of what it may have looked like:
Suddenly a woman enters the room. That in itself did not shock anyone; all of life was more public then than now. Additionally, Simon intentionally opened this dinner to visitors, since he was hosting a type of discussion forum with Jesus as the main attraction.
Nor does the scandal come from the woman’s seeking attention. She wanted to remain hidden from the crowd while she offered her most valuable possession to Jesus. She heard him preach earlier; she recognized in him God’s mercy and love, and she found forgiveness in his message of grace. She (earlier) accepted Jesus’ salvation; now she comes to give thanks for the freedom she found from the things she left behind.
The picture shows how she could “stand behind him at his feet.” Overcome with joy for forgiveness, she begins to cry. Unintentionally, her tears fall on the feet of Jesus. Without a towel, she instinctively pulls her hair around to wipe up the mess her tears made as they cut little rivulets in the dust clinging to his feet. Now overcome with emotion and touching the Lord to intimately, she kisses the feet she had just so tenderly bathed. Then in a rash act of devotion, she opens the alabaster flask and begins to rub Jesus’ cracked and worn feet with scented oil.