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Matthew 6:16
ESV "And when you fast, do not look gloomy like the hypocrites, for they disfigure their faces that their fasting may be seen by others. Truly, I say to you, they have received their reward.
NIV "When you fast, do not look somber as the hypocrites do, for they disfigure their faces to show others they are fasting. Truly I tell you, they have received their reward in full.
NASB Now whenever you fast, do not make a gloomy face as the hypocrites do, for they distort their faces so that they will be noticed by people when they are fasting. Truly I say to you, they have their reward in full.
CSB "Whenever you fast, don’t be gloomy like the hypocrites. For they make their faces unattractive so that their fasting is obvious to people. Truly I tell you, they have their reward.
NLT And when you fast, don’t make it obvious, as the hypocrites do, for they try to look miserable and disheveled so people will admire them for their fasting. I tell you the truth, that is the only reward they will ever get.
KJV Moreover when ye fast, be not, as the hypocrites, of a sad countenance: for they disfigure their faces, that they may appear unto men to fast. Verily I say unto you, They have their reward.
NKJV “Moreover, when you fast, do not be like the hypocrites, with a sad countenance. For they disfigure their faces that they may appear to men to be fasting. Assuredly, I say to you, they have their reward.

What does Matthew 6:16 mean?

Jesus has already taught His disciples not to call attention to themselves in public when they give to the needy (Matthew 6:3–4) and when they pray (Matthew 6:6). He has called attention-seekers hypocrites who act out worship God for the praise of other people (Matthew 6:2).

Now He begins to apply the same basic lesson to fasting. Fasting involves abstaining from food and other activities in order to focus on worship, confession, or specific prayers to God (Matthew 4:1–2). Fasting was a regular part of worship for faithful Israelites. The law required fasting once a year on the Day of Atonement (Leviticus 23:27–32), though other seasons of fasting had been added to the Jewish calendar over time. In addition, individuals might fast in order to indicate repentance before God or to bring special requests to Him in times of great need.

The Old Testament commands to fast can be translated with the words "afflict yourself" (Numbers 29:7). In Jesus' era, it seems some religious leaders made a point to do this very publicly. The group known as the Pharisees had a reputation as the most strictly religious people in Israel. They were intensely proud of that status. Scholars suggest the Pharisees fasted two days every week. Jesus says in this verse they disfigured their faces in some way and looked "gloomy" to make sure that everyone who saw them knew they were fasting.

This quest for publicity worked. People saw them, understood they were fasting yet again, and gave them credit for being highly devout. Jesus says here that human approval is the only reward attention-seekers will receive for their fasting. Since their effort was not about God, God will not respond or reward them for it. God said the same to their ancestors about fasting with no real heart change (Zechariah 7:5–6; Matthew 5:20; 6:16–18).
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