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What the Fathers say
Eastern Fathers
John Chrysostom
As therefore, when He said, "Let not thy left hand know what thy right hand doeth," it was not of hands that He was speaking, but of the duty of being strictly concealed from all; and as when He commanded us to enter into our closet, not there alone absolutely, nor there primarily, did He command us to pray, but He covertly intimated the same thing again; so likewise here, in commanding us "to be anointed," He did not enact that we positively must anoint ourselves; for then we should all of us be found transgressors of this law; and …
Theophylact of Ohrid
"But thou, when thou fastest, anoint thine head, and wash thy face; that thou appear not unto men to fast, but unto thy Father Who is in secret: and thy Father Who seeth in secret shall reward thee openly." Men of old would anoint themselves with oil after bathing as a mark of their joy and well-being. So you also, O reader, should appear joyful when you fast. The oil used to anoint we also understand to mean almsgiving. …
Western Saints
Augustine of Hippo
A question is here wont to be raised; for none surely would literally enjoin, that, as we wash our faces from daily habit, so we should have our heads anointing when we fast; a thing which all allow to be most disgraceful. (ubi sup.) Or; by the head we rightly understand the reason, because it is preeminent in the soul, and rules the other members of the man. Now anointing the head has some reference to rejoicing. …
Jerome
But when you fast, anoint your head and wash your face, so that you may not appear to be fasting to men, but to your Father who is in secret: and your Father who sees in secret will repay you. He is speaking according to the custom of the province of Palestine, where they usually anoint their heads on festive days. Therefore, he commanded us to show ourselves joyful and festive when we fast. Those reading it from the Psalmist: The oil of the sinner shall not anoint my head (Ps. …
Gregory the Dialogist
For God approves that fasting, which before His eyes opens the hands of alms. This then that you deny yourself, bestow on another, that wherein your flesh is afflicted, that of your needy neighbour may be refreshed.
Translation