Simon the Pharisee thinks he is an expert in judging people and he thinks there are two kinds of people – good people and sinners. The difference, in his mind, is that good people keep the law and sinners don’t.
He is trying to make up his mind about Jesus. Other people think Jesus is a prophet but Simon sees him breaking the law, allowing himself to be touched by a known sinner. So Simon thinks Jesus can’t be much of a prophet because either he doesn’t know what kind of woman is touching him or he doesn’t care. He thinks Jesus is not very good at reading people, but Jesus has read him perfectly.
Jesus is trying to teach Simon to see people differently, as God sees us. We are all sinners. Some of us pretend that we’re not and try to justify ourselves by observing the letter of the law and comparing ourselves with others who are clearly greater sinners than we are, so that we feel no need of forgiveness. Simon is one of those people. Because he has never acknowledged his sins, he doesn’t know what it feels like to be forgiven.
The unnamed woman in the story is also a sinner but somehow, through Jesus, she has come to know the boundless mercy of God, and that is why she is filled with an overwhelming desire to express both her sorrow and her love. The tears she sheds over Jesus’ feet are not tears of remorse, but tears of gratitude.
Jesus wants Simon to see this woman. Not just ‘this sort of woman’ as Simon has already identified her, but this actual woman, her tears, her hair, her kisses, her perfume and her extravagant love. Jesus holds her up as a mirror to Simon, contrasting each of her loving actions with Simon’s coldness, hoping that he will see himself as he is and as he could be. If only he would acknowledge his sins and accept the mercy of God, he too could be overflowing with love.
The gospel doesn’t tell us whether Simon learnt that lesson and responded to the forgiveness of God which is offered not just to judgmental hypocrites like him but even to murderers like King David, because that doesn’t matter now. What matters is whether we have learnt the lesson and opened our hearts to the forgiveness which is so powerful that it can call forth such extravagant love.