(Luke 7:36-50)
When Luke writes of Jesus' relationship with the Pharisees, it was not to cast doubt on the theological position of the Pharisees, but to contrast the difference between how they, and Jesus, approached the Old Testament Scripture in relation to daily living. Jesus and the pharisees agreed more than disagreed on their interpretation of the Pentateuch (first five books of the Old Testament). Many Pharisees were pious, God-fearing Jews looking for the deliverance of the Messiah. Jesus was a loyal Jew, who accepted the authority of the Torah. Jesus had many friendly encounters with the Pharisees (Luke. 7:36; 11:37; 13:31-33; 14:1; Mark 12:28-24; Matthew 23:1-2).

The title "Pharisee" should not be synonymous with "hypocrite." Jesus' contention with the Pharisees was their self-righteous separation from outsiders, pride in sole accomplishment, and lack of charity and sympathy. They represented both the best and worst of Jewish religious thought and practice.
(William Benton, Pub., The New Encyclopedia Britannica in 30 Volumes, S.V. "Biblical Literature" by R.M.A. Everett Ferguson, Backgrounds of Early Christianity, 2nd Edition Grand Rapids, Michigan, William B. Eerdmans Publishing Co., 1987, 483-4.) (James Hasting. DD ed. Dictionary of The New Testament: Christ and The Gospels, S.V. "Pharisees" by H. M. Scott.)

Hebrew Law and Custom

The custom of the day was that the host would greet his male guest with a kiss on the cheek, and often anoint his head with olive oil or perfume. When a dinner party was planned, the host would provide for the washing of the feet of the guest. Sandals were the footwear of the time and the majority of the roads were unpaved, so the feet of the traveler would often be dusty or muddy. As told later in the narrative, Simon failed to provide his guest, Jesus, with any of these courtesies. Simon may have invited Jesus to his home for dinner, but it was not to honor Him or learn from Him--most likely to look for a means to entrap or discredit Jesus.

For special dinner parties, small couches were brought in for the guests to recline on while eating. Jesus' feet would have been away from the table and He would have removed His sandals upon entering the house. Neighbors and uninvited guests were allowed to attend a party and stand along the wall or crouch down and listen to the guest rabbi or teacher, but were not expected to intervene or interact.

The arrival of the woman, who was characterized as a sinner (probably a prostitute) was unexpected. It was unheard of for such a person to come into the home of a Pharisee at such an occasion. Her tears, anointing, and kissing of His feet instead of His head demonstrated a humility and feeling of unworthiness to approach Jesus formally. The woman's respect and submission to Jesus' authority most likely pointed to a desire for forgiveness for her many sins.
(J. Vernon McGee, Thru The Bible With J. Vernon McGee, Nashville, Tennessee, Thomas Nelson, Inc., Publishers, 1983, 4:278-80.) (John F. Walvoord, Roy B. Zuck, ed. The Bible Knowledge Commentary, Wheaton, Illinois: Victor Books, 1983, 223-4.)