The Parable. . 41 “Two people were in debt to a certain creditor; one owed five hundred days’ wages and the other owed fifty. 42 Since they were unable to repay the debt, he forgave it for both. Which of them will love him more?” 43 Simon said in reply, “The one, I suppose, whose larger debt was forgiven.” He said to him, “You have judged rightly.”
The gist of the parable centers on the creditor who becomes a gracious benefactor, cancelling the debts of his clients. The clients have done nothing to repay debt – both seem beyond the capacity of the clients to payback. The dynamics of creditor/debtor would have been something well familiar to Simon (as it appears he is relatively wealthy in throwing a public dinner affair). He would have been quite familiar and comfortable in the quid pro quo to invitations, reciprocal invitations, and the inherent social status implied in the dynamic. The cancellation of such debts, strips away the “rules” by which interpersonal interactions were managed.
Jesus moves the parable to a new footing when he asks, not about indebtedness, but about love. Which of the two debtors will love more? I would suggest, that Simon, to his credit, engages the question honestly. Some commentators claim he is edging his bets with “The one, I suppose…” indicating a begrudging response or a cautious reply while he considers the implications. I would offer that because Jesus is moving the foundation of the relationship from honor/indebtedness to love, Simon is simply moving reflectively on this new foundation. His earlier response, “Tell me, teacher” is an honest one. Simon has taken a place, at least momentarily, as a student. And the teacher affirms him “You have judged rightly.”
Jesus continues his lesson: Then he turned to the woman and said to Simon, “Do you see this woman? Green  writes that as Jesus turns to the woman “while speaking to Simon momentarily reduces her from the role of central actor to that of object lesson. This is important for the rhetoric of the narrative, however, for in this way Jesus hopes to persuade Simon to adopt Jesus’ own view of matters concerning this woman. He wants to transform Simon’s view of the world and so to have Simon reconsider his premature judgment regarding this woman. Jesus’ opening query, “Do you see this woman?” is an invitation to enlightenment, the consequence of which would be acceptance of both her (i.e., no longer viewing her as a ‘sinner’ but as one who loves extravagantly) and of new behaviors modeled on those of this woman.”
Our narrative began, not with Jesus’ reception into Simon’s house, but with the scandalous actions of the woman. It is only now that we learn about Simon’s actions – and in comparison to the woman’s. When I entered your house, you did not give me water for my feet, but she has bathed them with her tears and wiped them with her hair. 45 You did not give me a kiss, but she has not ceased kissing my feet since the time I entered. 46 You did not anoint my head with oil, but she anointed my feet with ointment.
Perhaps too much is made of the demands of hospitality: water with which to wash his feet, kiss of welcome, and oil for anointing his head. None of these was required, but they were gracious gestures of hospitality attested elsewhere (foot-washing: Genesis 18:4; 19:2; Judges 19:21; 1 Samuel 25:41; John 13:3–5; a kiss of greeting: 2 Samuel 15:5; Luke 15:20; 22:47–48; anointing with oil: Psalms 23:5; 133:2; Mark 14:3). None of them were expected of the woman, but she was the one who provided them. We should not think, however, that the woman’s actions simply substituted for Simon’s. Instead, her ministrations on Jesus’ behalf are notable for their lavishness. Why?
The focus is not on fulfilling requirements, but gratitude as the foundational reason for the action. The effect of Jesus’ words is to connect the Simon’s right answer to Jesus’ parable to Simon’s wrong judgment of the woman who anointed Jesus’ feet. [Culpepper, 172]
Each of the people in the narrative – Simon and the woman – are debtors, and Jesus then makes clear that the parable is not about the reconstruction of social norms or first century economics, but about sin, forgiveness, and love.