My head with oil - The custom of pouring oil upon the head was universal among the Jews. The oil used was sweet oil or oil of olives, prepared in such a way as to give an agreeable smell. It was also used to render the hair more smooth and elegant. See Ruth 3:3; 2 Samuel 12:20; 2 Samuel 14:2; Psalm 23:5.

With ointment - This "ointment" was a mixture of various aromatics, and was therefore far more costly and precious than the "oil" commonly used for anointing the head. Her conduct, compared with that of Simon, was therefore more striking. "He" did not give even the common oil "for his head" used on such occasions. "She" had applied to "his feet" a far more precious and valuable "unguent." "He" therefore, showed comparatively "little" love. "She" showed "much."

My head with oil thou didst not anoint - Anointing the head with oil was as common among the Jews as washing the face with water is among us. See Ruth 3:3; 2 Samuel 12:20; 2 Samuel 14:2; 2 Kings 4:2; and Psalm 23:5, where the author alludes to the Jewish manner of receiving and entertaining a guest. Thou preparest a table for me; anointest my head with oil; givest me an overflowing cup. See Matthew 5:17.

Mine head with oil thou didst not anoint,.... No not with common oil, so usually done at feasts, see Psalm 23:5

but this woman hath anointed my feet with ointment; even "with ointment" "of spices", as the Syriac version renders it. There is, throughout the whole account, an opposition between the conduct of Simon, and this woman: he gave him no common water to wash his feet with, she shed floods of tears, and with them bathed his feet, and then wiped them clean with the hairs of her head; he gave him not the usual salutation by kissing his head or lips, but she kissed his feet, and that over and over again; he did not so much as anoint his head with common oil, when she anointed his feet with costly ointment brought in an alabaster box. These several ceremonies to guests were used by their hosts, in other nations, such as washing, anointing, and kissing (c).

(c) Vid. Apuleii Metamorph. i. 1. prope finem.

Oil (ἐλαίῳ)

In Luke 7:37, Luke 7:38, the word μύρον, liquid ointment, is used. This was the finer and costlier of the two. Christ means to say to Simon, "thou didst not anoint my head, the nobler part, with ordinary oil. She hath anointed my feet with costly ointment.

My head with oil thou didst not anoint: but this woman hath anointed my feet with ointment.

7:44-46 I entered into thine house. How strong the contrast between the indifference of the Pharisees and the earnestness of the penitent! He withheld water; she gave precious tears, the blood of her heart, says Augustine. He gave no kiss to his cheek; she covered his feet with kisses. He grudged even a drop of oil; she broke the box of rare ointment for her Lord. He treated him with despite as an underling; she adored him as a prince. The water for the feet, the kiss and the oil for the head were ordinary Oriental courtesies.

46. with oil . not anoint-even common olive oil in contrast with the woman's "ointment" or aromatic balsam. What evidence was thus afforded of any feeling which forgiveness prompts? Our Lord speaks this with delicate politeness, as if hurt at these inattentions of His host, which though not invariably shown to guests, were the customary marks of studied respect and regard. The inference is plain-only one of the debtors was really forgiven, though in the first instance, to give room for the play of withheld feelings, the forgiveness of both is supposed in the parable.

7:36-50 None can truly perceive how precious Christ is, and the glory of the gospel, except the broken-hearted. But while they feel they cannot enough express self-abhorrence on account of sin, and admiration of his mercy, the self-sufficient will be disgusted, because the gospel encourages such repenting sinners. The Pharisee, instead of rejoicing in the tokens of the woman's repentance, confined his thoughts to her former bad character. But without free forgiveness none of us can escape the wrath to come; this our gracious Saviour has purchased with his blood, that he may freely bestow it on every one that believes in him. Christ, by a parable, forced Simon to acknowledge that the greater sinner this woman had been, the greater love she ought to show to Him when her sins were pardoned. Learn here, that sin is a debt; and all are sinners, are debtors to Almighty God. Some sinners are greater debtors; but whether our debt be more or less, it is more than we are able to pay. God is ready to forgive; and his Son having purchased pardon for those who believe in him, his gospel promises it to them, and his Spirit seals it to repenting sinners, and gives them the comfort. Let us keep far from the proud spirit of the Pharisee, simply depending upon and rejoicing in Christ alone, and so be prepared to obey him more zealously, and more strongly to recommend him unto all around us. The more we express our sorrow for sin, and our love to Christ, the clearer evidence we have of the forgiveness of our sins. What a wonderful change does grace make upon a sinner's heart and life, as well as upon his state before God, by the full remission of all his sins through faith in the Lord Jesus!