As the woman of ill repute continues washing Jesus’ feet, He says to his host, the Pharisee, “Simon, there were two debtors. One owed a vast sum and one a pittance, but neither was able to repay their lender. So the lender forgave both men of their debt. Which of the two men will love the lender more?” With initial silence just for emphasis, Simon then declares, “The one who owed the most will love the most.” And with this answer Jesus’ spiritual trap is set.
“Simon, when I entered your home you failed to greet me properly. You did not kiss me, you did not anoint my head with oil, and you gave me no water to wash the dust from my feet. This woman has anointed my feet with perfume. She has washed them with her tears and has not stopped kissing them since she fell at them in humiliation.” And now Jesus closes the net. “Simon, the man who is forgiven a great deal, loves a great deal. The man who is forgiven only a little, loves only a little.”
Simon’s “small” failures, compared to the gross sins of the prostitute, blinded him to his own need. He believed his overall goodness, compared to the woman’s overall badness, gained him standing with God. Even his failures, such as they were, were of more value than this woman’s life of humiliating debauchery.
Who had the greatest need in the room that evening? The prostitute humiliated by sin or the Pharisee who believed even his failures were worth something to God compared to prostitution?