For the Jewish community of Jesus’ day, the three primary expressions of piety were charity, prayer, and fasting. In verses 16-18 the matter of fasting is discussed. The only official Jewish day of fasting was the Day of Atonement, when eating, drinking, bathing, and anointing with oil were forbidden. The Jews would also fast in connection with the celebration of days of national disaster, and it was frequently done on a private and individual basis as well.
As we said in the discussion of 4.2, fast means to deliberately go without food, usually as a way of honoring God or as part of a period of meditation and prayer. The custom is known in many parts of the world and poses no translation problem in such places. Where it is not known, translators can say “Whenever you go without food to honor God” or “On those occasions when you do not eat so you can worship God.”
Dismal (Good News Translation “sad face”) translates a word used in the New Testament only here and in Luke 24.17. It may be used of one who looks angry, sullen, or sad. In the Septuagint it is used to describe the chief baker and the wine steward of the king (Gen 40.1). A number of translations render it with the meaning “gloomy” (New Jerusalem Bible, New English Bible, An American Translation, Moffatt, Barclay). To look dismal can be “to go about looking pitiful (or sad, or gloomy).”
The word hypocrites is first used in Matthew 6.2 (see comments there). The real point is that the hypocrites are intentionally acting in such a manner as to draw attention to themselves. Translators may say “that is what the hypocrites do” or “that is how the hypocrites show (or, present) themselves.”
Disfigure their faces (so also New International Version, Barclay) is translated “neglect their appearance” by Good News Translation and “neglect their personal appearance” by An American Translation. Jerusalem Bible renders “pull long faces” and New English Bible “make their faces unsightly.” One commentator notes that the Greek verb translated disfigure appears not to be used elsewhere with “face” as its object, and he suggests that it was chosen here because it rhymes with the Greek verb rendered may be seen. For other occurrences of the Greek verb for disfigure, see verses 19, 20 (“consume”) and Acts 13.41 (“perish”). Some commentators limit disfigure their faces to the matter of leaving them unwashed. Others extend the meaning to include leaving their faces unwashed and their hair uncombed and the strewing of ashes on their heads. For English speakers the problem with disfigure is that it may imply a permanent action, whereas the reference is limited to things done during days of fasting.
It is important to show that when the hypocrites disfigure their faces, it is a deliberate thing. Thus the phrase can be rendered “they deliberately go with dirty faces (or, unkempt appearances),” “they make themselves appear to be suffering,” or “they allow themselves to look terrible.”
That their fasting may be seen by men is inverted by Good News Translation: “so that everyone will see that they are fasting.” In the context men is used inclusively of “people,” and so New English Bible translates “so that other people may see that they are fasting” (New American Bible “so that others may see they are fasting”).
Some translations make this a new sentence, as in “They do that so everyone can see they are fasting” or “They do that to make sure people know they are fasting.”
Truly, I say to you: see 5.18, where almost the precise form is used; see 5.20 for the exact words.
They have received their reward: see comments on Matthew 6.2.
Quoted with permission from Newman, Barclay M. and Stine, Philip C. A Handbook on the Gospel of Matthew. (UBS Handbook Series). New York: UBS, 1988. For this and other handbooks for translators see here .

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