So here, we have the situation of Simon, a Pharisee who welcomes Jesus into his home. He sees Jesus’ signs of healing and teaching and seeks to understand this Jesus who is causing a sensation wherever he goes.
This woman, discovering Jesus was at the Pharisee's house, sought Jesus out, slipping into this home without an invitation. At that time, people were crowding around Jesus wherever he went. Had this woman encountered Jesus previously? Perhaps she met him before or witnessed something he said or did. Either way, she somehow recognizes who he is.
The Pharisee is hospitable to Jesus but only half-heartedly. It must have been customary to offer water to honored guests to wash their feet before they came into a house since people at that time wore sandals and walked on dirt roads. And it also must have been customary to greet your guests with a kiss and anoint them with oil as a sign of honor and respect.
Being a Pharisee, Simon had studied since he was a young man and devoted himself to follow the Law and its traditions to the letter. Highly respected by his community, he is filled with pride and arrogance, analyzing everything with intellectual skepticism and control. He also knew all the Biblical laws broken by this woman that made her so sinful. She is his polar opposite. Uneducated of any religious knowledge she is scorned because of her sinfulness, her life run by her feelings and impulses. Just by being female she is a 2nd class citizen. She pours her heart out to Jesus in humility with only her belief in him. By contrast, Simon is cold and restrained toward her and Jesus, smug in his self-righteousness.
In this room full of people, this woman comes behind a reclining Jesus at his feet. She is too ashamed to look him eye to eye, but out of fear and humility, she cowers behind him on the ground, weeping, saying nothing, but honoring him the only way she could.
"What is SHE doing here?" Simon must have thought. Even though it is the woman coming to Jesus, he uses this to discredit him, saying to himself that if he really is a prophet, he would know this woman is a sinner and would never let her touch him, let alone cry on him. Simon found this scenario appalling and embarrassing. The room must have been hushed except for the woman's sobbing. Jesus gives Simon an opportunity to understand the vast difference between him and this woman, by telling him the parable.
“Simon, I have something to say to you.” And he replied, “Say it, Teacher.”
“A certain moneylender had two debtors: one owed five hundred denarii and the other fifty. “When they were unable to repay, he graciously forgave them both. Which of them therefore will love him more?” Simon answered and said, “I suppose the one whom he forgave more.” And He said to him, “You have judged correctly.” Turning toward the woman, he said to Simon:
“Do you see this woman? I entered your house; you gave me no water for my feet, but she has wet my feet with her tears, and wiped them with her hair. “You gave me no kiss, but she, since the time I came in, has not ceased to kiss my feet. “You did not anoint my head with oil, but she anointed my feet with perfume. “For this reason I say to you, her sins, which are many, have been forgiven, for she loved much; but he who is forgiven little, loves little.” And he said to her, “Your sins have been forgiven.”
Pharisees especially did not come into physical contact with Gentiles and sinners because their sin or something unclean they may have touched would transfer to them and defile them. By allowing this woman to touch him, Jesus has taken her sin onto himself and has cleansed her through his forgiveness. She didn’t ask for forgiveness. Jesus forgave her sins because that was what she needed. No one else forgave her, which is why she had her reputation. She might even have been kept out of the temple, unable to worship God. People branded her thus trapping and labeling her for the rest of her life. They were not allowing any way out for this woman who made mistakes in her life.
And Jesus beholds her make-up smeared face of mud and perfume and looking into her swollen eyes he says,“Your faith has saved you; go in peace.”
This immoral woman, whom everyone thought was the lowest of the low, was accepted by Jesus because she loved him. She didn’t say anything to Jesus, she didn’t change her ways before presenting herself, and neither did she take a vow to be perfect. She probably didn't even know what she wanted from Him. And Jesus doesn't ask anything of her.
