Simon had not extended to Jesus even the common courtesies offered to guests. He had not called for a servant to wash the dust from His feet. He had not greeted Jesus with a kiss on the cheek, which was the normal custom for welcoming a guest into one’s home. How would you feel if you visited my house during the winter and I did not offer to take your coat or even shake your hand? The absence of such customary courtesies would make you feel unwelcome.
What is obvious is that Simon did not love Jesus. He did not think he needed Jesus. Jesus did not let Simon off the hook. He pointed out that, had this woman not come in, His feet would have gone unwashed and His cheek unkissed. He also reminds Simon that he had not anointed His head with oil.
In poorer homes, inexpensive oils would be used, but a man like Simon would often pour a bit of extravagant perfume from exotic herbs and spices on the head of his guests. The hair and clothing of the guests would exude the sweet fragrance of the oil for days and they would remember their gracious host and the wonderful hospitality he had offered.
Simon did not think Jesus deserved to have His cheeks kissed, His feet washed and certainly not His head anointed with costly perfume. He had treated Jesus the way a spoiled child might treat a nerdy cousin his mother made him invite to his birthday party. Oh, but not the woman from the streets! She washed His feet with her tears, continually kissed them and brought her own perfume to the party. To me, the lesson is not to get caught up in myself and tradition; love extravagantly.