I am surprised over the many commentaries I read that wrote about this section of Scripture, saying that Simon needed forgiveness. Yet, when the Lord spoke privately to Simon and presented to him the parable of the two debtors, he revealed in the context of the parable that both were forgiven their debts forthrightly. It therefore follows that that both Simon and the woman were forgiven. Otherwise, the parable has little meaning for Simon. Therefore, it was not forgiveness that Simon needed but a greater capacity to love Jesus.
In previous studies I have shown that it is probably true that Simon was one of Jesus apostles, and he lived in Bethany with his wife Martha, and the unnamed woman in Luke 7 is his sister-in-law, Mary (who is also Mary Magdalene). In Matthew and Mark he is referred to as Simon, the leper (Matthew 26:6; Mark 14:3), implying Jesus must have healed him on some previous occasion. If this is true, then Jesus must have healed Simon prior to the meal he held in Jesus’ honor in Luke 7:36-50. The only specific healing in any of the Gospel records, where Jesus healed a man of his leprosy, is found very early in Jesus’ ministry in Luke 5:12-14 (cf. Matthew 8:2-4; Mark 1:40-45). While this doesn’t amount to proof that Simon, the leper, was healed in the first month of Jesus’ ministry, it stands to reason that, if Simon, the leper, was one of the Twelve, he would necessarily have been healed very early in Jesus’ public ministry, and Luke 5:12-14 may very well be that event.
Let’s consider now what Jesus said to Simon, the Pharisee, at the dinner he held in Jesus’ honor. Jesus would have taken his place at the table to Simon’s immediate right, the place of honor. Knowing this, when he spoke with Simon, Jesus would have leaned upon Simon’s breast and spoke softly and privately with him. Not even the woman at Jesus’ feet would have heard what Jesus said to him. Jesus mentioned that Simon didn’t kiss him when Jesus entered his home. A kiss was often given as a greeting or upon entering another’s dwelling (cf. Genesis 27:26; 29:13) and was a sign of one’s love or affection toward that person (Genesis 48:10). Luke doesn’t tell us why Simon didn’t do this, but it may have been because of the others at the table with them (cf. Luke 7:49). They may very well have been other Pharisees and perhaps rabbis, who were friends with Simon. In other words, Simon cared more for the esteem in which these men held him, than for Jesus who had healed him and called him to be an apostle. What a picture this is, and how often we, who have come to trust in Jesus, are guilty of doing similar things that reveal our care for men’s admiration over our love for our Lord.
On the other hand, the woman hadn’t ceased kissing the Lord’s feet, even weeping and letting her tears fall upon them, and drying them with her hair (Luke 7:44-45). Such a thing was a sign of her love or deep affection for Jesus (cf. Genesis 45:14-15; Ruth 1:9; 1Samuel 20:40-42).
Moreover, Jesus pointed out that neither did Simon offer Jesus the common courtesy of having a servant wash Jesus’ feet (Luke 7:44). One has to wonder if Simon was so tactless with all of his guests, or did he simply ignore this courtesy for Jesus. If so, Jesus probably arrived at Simon’s home later than the others, and Simon forgot to offer the courtesy, or, more probably, he didn’t want to keep his friends waiting at the table, so he had Jesus take his place immediately.
In such a context, Simon seems to have been caught up in pleasing the persons of men to the point of overlooking the opportunity to express his affection for Jesus. One might even say he was ashamed of his relationship with his Lord in the presence of those whose good esteem Simon desired (cf. Luke 9:23-26; Matthew 10:32-33; Mark 8:38). On the other hand, the woman, whom I have identified in a previous study as Mary, Martha’s sister, expressed shameless affection for Jesus, because of what he had already done for her (Luke 7:42, 48; cf. 8:2). If Simon knew her and thought of her as a sinner, certainly, at least most of Simon’s guests would have known her and believed likewise. So, Mary was not in friendly company, and she probably knew it. Yet, she had no regard for herself except to express her shameless love for Jesus.
 Mary’s sins were forgiven at some time previous to this dinner. Luke 7:42 puts them in the past (Aorist tense). Luke 7:48 is in the perfect tense and places the event in the past and doesn’t need to be done again at the dinner or any other time in the future. The forgiveness took place sometime in the past, and Luke 8:2 tells us that Jesus had cast out seven demons from her life. What Simon had forgotten was that healing amounts to forgiveness (cf. Luke 5:20-24), something his guests refused to admit (Luke 5:21, 7:49; cf. Luke 5:26; Mark 2:12).