It is amazing that John’s disciples had joined the Pharisees and challenged Jesus too! But it is possible that John’s disciples had been taught by John to avoid feasting and wine (Luke 7:33). John apparently was an esthetic and as a result his own disciples probably avoided feasts and the drinking of wine. Now that John was in prison, they would not have been able to get his advice and know how to respond to Jesus’ conduct. This could help explain why John’s disciples also asked Jesus the same question.

But it is not surprising that the Pharisees asked this question. The Mosaic Law taught that they were supposed to fast on the day of Yom Kippur, the Day of Atonement (Lev. 16:29-34). But the Pharisees had added to God’s command and required that every Jew fast on Monday and Thursday of each week.

Thursday was selected for a fast because they believed that Moses had climbed Mount Sinai on a Thursday. Monday was selected because they believed that Moses had come down the mountain on that day. Therefore according to the rabbis, every Jew was expected to fast two times each week (Luke 18:12). So it appears that Matthew’s party occurred on either a Monday or a Thursday. If this is true, then Jesus and His disciples were feasting on a day when, according to the Pharisees, they should have been fasting. If so, they were in direct violation of the Pharisees’ rules.

The rabbis had decreed that no one could eat anything larger than a date on the Day of Atonement. Also, they were to avoid such things as eating, drinking, bathing, anointing oneself, wearing sandals, and having sexual relations on fast days (Mishna Yoma 8.1).

We will discuss fasting in more detail when we come to the Sermon on the Mount, but for now we will simply say that the Jewish fast involved the avoidance of many things and not just food. They had added many days of fasting and a long list of prohibitions not required by God. When the Pharisees fasted, they also put on a gloomy face and looked shabby. That is why Jesus said this to a crowd of people during the Sermon on the Mount,