The idea that sins are debts to God is well known in Judaism and appears elsewhere in the teaching of Jesus [e.g. Matt. 18:21-35]. Canceling of debts may have been subversive to some since it went against the inequality and hierarchy of the client-patron relationship, but it would not have been subversive to Jews familiar with Deut. 15:1-3 [about granting release of debts every seven years] and the year of Jubilee (Lev. 25:10-55), both of which call for canceling of debts. Jesus’ adaptation of Isaiah 61 recorded in Luke 4:16-21 is almost certainly to be understood as an announcement of the eschatological Jubilee, and this parable, like the Parable of the Unforgiving Servant, assumes that the Jubilee has begun and that God is in the process of canceling debts, i.e. forgiving sins. This parable expresses the grace and the goodness of God. When it comes to forgiveness, God is like a moneylender who does not care about money. (Stories With Intent: A Comprehensive Guide to the Parables of Jesus, p. 87)
NKJ Luke 7:36 Then one of the Pharisees asked Him to eat with him. And He went to the Pharisee’s house, and sat down to eat.
NKJ Luke 7:37-38 And behold, a woman in the city who was a sinner, when she knew that Jesus sat at the table in the Pharisee’s house, brought an alabaster flask of fragrant oil, 38 and stood at His feet behind Him weeping [Pres. Act. Part. > κλαίω, continually weeping]; and she began to wash His feet with her tears, and wiped [Impf. Act. Ind. > ἐκμάσσω, NASB appropriately has kept wiping] them with the hair of her head; and she kissed His feet and anointed them with the fragrant oil.
NKJ Luke 7:39 Now when the Pharisee who had invited Him saw this, he spoke to himself, saying, “This Man, if He were a prophet, would know who and what manner of woman this is who is touching Him, for she is a sinner.”
NKJ Luke 7:40 And Jesus answered and said to him, “Simon, I have something to say to you.” So he said, “Teacher, say it.”
NKJ Luke 7:41-42a There was a certain creditor who had two debtors. One owed five hundred denarii, and the other fifty. 42 And when they had nothing with which to repay, he freely forgave [χαρίζομαι, NASB has graciously forgave] them both.
Third, it is significant that both debtors were freely forgiven. Simon should have realized that, whether he viewed his own sins as being as great as the woman’s or not, forgiveness for both can only come as a free gift and not something that is earned. In fact, Jesus emphasized this idea with the very word He used to describe forgiveness, the Greek verb charízomai, which comes from the noun charís, meaning grace. It definitely carries the meaning, then, of freely forgiving or, as in the NASB, graciously forgiving.
NKJ Luke 7:42b-43 “Tell Me, therefore, which of them will love him more?” 43 Simon answered and said, “I suppose the one whom he forgave more.” And He said to him,“You have rightly judged.”
NKJ Luke 7:44-46 Then He turned to the woman and said to Simon, “Do you see this woman? I entered your house; you gave Me no water for My feet, but she has washed My feet with her tears and wiped them with the hair of her head. 45 You gave Me no kiss, but this woman has not ceased to kiss My feet since the time I came in. 46 You did not anoint My head with oil, but this woman has anointed My feet with fragrant oil.”
After Simon answers [Jesus’ question] correctly, Jesus asks if he sees “this woman.” Clearly Simon sees her reputation, not her, and is this not frequently still the problem, that we see systems and concerns but not people? This is not to say that concerns about sin or other issues are not important, but if Jesus did anything, he actually saw people. (Stories With Intent: A Comprehensive Guide to the Parables of Jesus, p. 87)
NKJ Luke 7:47 Therefore I say to you, her sins, which are many, are forgiven, for she loved much. But to whom little is forgiven, the same loves little.