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; 2Sa 12:20; 2 Samuel 14:2; Psalms 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.”