Matthew 6:17 But you, when you fast,

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Sermon on Mount, law and fulfillment, visible and hidden, debts and repayment, virtue and virtue signaling, 

KJV

Matthew 6:17 But thou, when thou fastest, anoint thine head, and wash thy face;

NIV

Matthew 6:17  But when you fast, put oil on your head and wash your face,

LISTENERS HEARD

You, however, abstaining? Oil your head! And your face? Wash up!

MY TAKE

To make a sacrifice, we must hide our sacrifice.

LOST IN TRANSLATION

The KJV adds words here to make a sensible written sentence out of what is clearly a verbal interchange. This verse works much better if we understand it as addressed to a specific person (see this article on the difference between written and spoken language). This is a change from the previous verse, Matthew 6:16,where the "you" was addressed to the whole crowd.

The Greek word for "head" also means the completion of a thing. In bathing, oiling your head and face was the final act.

MW -- Missing Word  -- The pronoun repeats the information in the verb so it should be repeated in English like "you yourself."

IW - Inserted Word-- The phrase "when" doesn't exist in the source.

WF - Wrong Form -  The "fast" is not an active verb but a participle, "fasting."

IW - Inserted Word-- The phrase "on" doesn't exist in the source.

MW - Missing Word -- The word "the" before "face" is not shown in the English translation.

EACH WORD of KJV

But -- The Greek word translated as"but" means "but". In the previous verse, this word was translated as "moreover." Since it appears in the second position, it works more like our word "however".

thou,  -- (MW) The pronoun is used here explicitly as the subject of the sentence. Since this information is already in the verb, the sense is repetitive as we say "your yourself."  There is no verb "to be" here in the Greek. However, when nouns, pronouns or adjectives appear in the form of a subject without a verb, the verb "to be" can be assumed.

when thou -- (IP) There is nothing that can be translated as "when thou" in the Greek source.

fastest,--  (WF) The Greek verb translated as "fastest" means the religious practice of abstaining. It is a present participle here, "fasting" or "abstaining," modifying the "you" that began the sentence.

anoint -- (WF) The word translated as "anoint" means putting oil on your skin after washing. This was a traditional Jewish practice to protect the exposed skin of the face and neck from the sun.  It was especially important to do on special occasions when it was considered part of good grooming. This is a command or request, not a statement.

thine -- The word translated as "thine" is the genitive form of the singular, second-person pronoun, which is most commonly the possessive form. This word comes before the definite article.

missing "the"  -- (MW) The untranslated word is the Greek definite article, "the." The Greek article is much closer to our demonstrative pronouns ("this", "that", "these", "those"). See this article for more. 

head, -- The term translated as "head", it means "head" and "top" but also the completion of a thing (as we say, "bringing it to a head"). It is also a metaphor for life ("losing your head" in Greek doesn't mean an emotional outburst, but being killed).

and -- The Greek word translated as "and" is used as the conjunction "and", but it also is used to add emphasis ("also"). The "and" here could be connecting the "wash" verb as in the KJV but it is more likely connecting "your head and your face."

wash -- The verb translated as "wash" specifically means washing up your hands and feet. It is not normally applied to bathing, which washed the whole body, including the head. "Washing up" was performed more frequently than bathing because the hands and feet got dirty more often. This word is the punchline, that is, the last word in the verse, which is unusual for a command.

thine -- The word translated as "thine" is the genitive form of the singular, second-person pronoun, which is most commonly the possessive form. This word comes before the definite article.

missing "the"  -- (MW) The untranslated word is the Greek definite article, "the." The Greek article is much closer to our demonstrative pronouns ("this", "that", "these", "those"). See this article for more. 

face; The word translated as "face" also means your appearance generally.

EACH WORD of NIV

But -- The Greek word translated as"but" means "but". In the previous verse, this word was translated as "moreover." Since it appears in the second position, it works more like our word "however".

when -- (IW) There is nothing that can be translated as "when thou" in the Greek source.

you,  -- (MW) The pronoun is used here explicitly as the subject of the sentence. Since this information is already in the verb, the sense is repetitive as we say "your yourself." 

fast -- (WF) The Greek verb translated as "fast" means the religious practice of abstaining. It is a present participle here, "fasting" or "abstaining," modifying the "you" that began the sentence.

put oil -- The word translated as "put oil" means putting oil on your skin after washing. This was a traditional Jewish practice to protect the exposed skin of the face and neck from the sun.  It was especially important to do on special occasions when it was considered part of good grooming. This is a command or request, not a statement.

on -- (IW) There is nothing that can be translated as "on" in the Greek source.

your -- The word translated as "your " is the genitive form of the singular, second-person pronoun, which is most commonly the possessive form. This word comes before the definite article.

missing "the"  -- (MW) The untranslated word is the Greek definite article, "the." The Greek article is much closer to our demonstrative pronouns ("this", "that", "these", "those"). See this article for more. 

head, -- The term translated as "head", it means "head" and "top" but also the completion of a thing (as we say, "bringing it to a head"). It is also a metaphor for life ("losing your head" in Greek doesn't mean an emotional outburst, but being killed).

and -- The Greek word translated as "and" is used as the conjunction "and", but it also is used to add emphasis ("also"). The "and" here could be connecting the "wash" verb as in the KJV but it is more likely connecting "your head and your face."

wash -- The verb translated as "wash" specifically means washing up your hands and feet. It is not normally applied to bathing, which washed the whole body, including the head. "Washing up" was performed more frequently than bathing because the hands and feet got dirty more often. This word is the punchline, that is, the last word in the verse, which is unusual for a command.

your -- The word translated as "your" is the genitive form of the singular, second-person pronoun, which is most commonly the possessive form. This word comes before the definite article.

missing "the"  -- (MW) The untranslated word is the Greek definite article, "the." The Greek article is much closer to our demonstrative pronouns ("this", "that", "these", "those"). See this article for more. 

face; The word translated as "face" also means your appearance generally.

COMPARISON: GREEK to KJV

σὺ (pron 2nd sg nom) "Thou" is from su which means "you" and "your."

δὲ (pronoun) "But" is from de which means "but" and "on the other hand." It is the particle that joins sentences in an adversarial way but can also be a weak connective ("and") and explanation of cause ("so") and a condition ("if").

νηστεύων (part sg pres act masc nom) "When thou fastest" is from nesteuo, which means "fast" and "to abstain from."

ἄλειψαί (2nd sg aor imperat mid) "Anoint" is from aleipho, which means "to anoint the skin with oil [as was done after bathing]", "anointing for gymnastic exercises", "of anointing [the sick]", "to supply oil for gymnasts", "to attend a gymnastic school", "to prepare as if for gymnastics,""to encourage", "to stimulate", "to instigate", "to daub", "to plaster", "to besmear,"and "to stop up ears."

σου (pron 2nd sg gen) "Thy" is from sou which means "you" and "your."

τὴν (article sg fem acc)  Untranslated is the Greek definite article, hos, ("the"). --

κεφαλὴν (noun sg fem acc) "Head" is kephale, which means "head of a man or beast", "an extremity", "the top", "the capital (top) of a pillar", "the coping of a wall", "the source of a rivalry," and, metaphorically the "crowning" or "completion" of a thing.

καὶ (adj) "And" is from kai, which is the conjunction joining phrases and clauses, "and," or "but." After words implying sameness, "as" (the same opinion as you). Used in series, joins positive with negative "Not only...but also." Also used to give emphasis, "even", "also," and "just."

τὸ (article sg neut acc)  Untranslated is the Greek definite article, hos, ("the"). --

πρόσωπόν (noun sg neut acc) "Face" is from prosopon, which means "face", "countenance." "in front", "facing", "front", "façade", "one's look", "dramatic part", "character", "in person", "in bodily presence", "legal personality", "person," and "feature [of the city, of a person]."

σου (pron 2nd sg gen) "Thy" is from sou which means "you" and "your."

νίψαι, (2nd sg aor imperat)"Wash" is from nipto, which means specifically "to wash hands or feet," and generally "to clean", "to purge," and "to wash off."

 

Wordplay

 The verbal image here is to appear as if for a feast while fasting. 

Unimportant Opinions and Imaginings

When the laughter died, the Master addressed the disheveled Messy Face directly.
“You yourself, however,” he said, waving for the youth to join him. “Fasting?”
We laughed because the answer was so obvious.
“Since sundown last night,” the youth answered as he walked through the crowd toward the speaker.
The Master smiled warmly and took the fasting youth’s hand as they met. The Master turned him around to face the crowd, displaying him for us. The Master then produced a small vial of oil from somewhere in his clothing and handed it to the young man.
“Oil your head!” the Teacher commanded him.
Many in the crowd applauded.
“Yes, Teacher,” the youth responded, happily taking the oil. He unstopped the vial, poured a little oil in his hand, and smoothed his hair.
The Master appraised his hair, nodded, and smiled approvingly. Then he produced a small rag and handed it to the young man.
“And that face of yours?” the Teacher continued. “Wash it!”
Again we laughed and applauded.

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