14 Then came to him the disciples of John, saying, Why do we and the Pharisees fast oft, but thy disciples fast not?
15 And Jesus said unto them, Can the children of the bridechamber mourn, as long as the bridegroom is with them? but the days will come, when the bridegroom shall be taken from them, and then shall they fast.
16 No man putteth a piece of new cloth unto an old garment, for that which is put in to fill it up taketh from the garment, and the rent is made worse.
17 Neither do men put new wine into old bottles: else the bottles break, and the wine runneth out, and the bottles perish: but they put new wine into new bottles, and both are preserved.
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The disciples of John the Baptist do not ask Jesus about fasting by chance: after all, among the Pharisees and among members of other religious brotherhoods, fasting was considered one of the basic religious rules, without the observance of which one could not speak of piety. At the same time, the original meaning of fasting had been thoroughly forgotten: fasting symbolized above all mourning, in particular mourning for dead relatives, as well, however, as mourning connected with events on a national scale.
Of course, in the course of the development of the Yahwistic, and later the Jewish, religious tradition, fasting acquired a new meaning, one connected with spiritual life proper: in religious life, fasting came to be associated with longing for God, with sorrow caused by the feeling of abandonment by God. And, of course, fasting became an expression of the fear and trembling that seize a person awaiting the near judgment of God; such, for example, was the fast of Yom Kippur.
But often in Gospel times fasting became simply a form of religious piety, an element of religious life obligatory for everyone and no longer connected either with concrete events in a person's life or with his spiritual state. This was the case, for example, among the Pharisees, who, judging by what we know of them today, fasted at least two days a week. The especially zealous members of the brotherhood did so even more often, and these fasts were often effectively public: those fasting demonstrated in every possible way their sorrow over their own sins, their fear and trembling before the approaching day of Judgment.
Jesus, however, restores fasting to its true meaning, not a religious meaning but a properly spiritual one. Fasting is not a religious obligation and not a rule of piety; it is the external expression of a particular spiritual state, especially abandonment by God. There is nothing here to imitate and no reason to do so: the time will come when fasting will become something completely natural, but for now there is no need for it, and it is not worth portraying a sorrow that does not exist.
Jesus, of course, does not frame the question this way by chance. After all, He is preparing His disciples and followers for life in the Kingdom. In the Kingdom there is no place for playacting and imitation, even if it is saturated with very important religious meanings. Here there is no longer any need for religion, just as there is no need here for symbols and allegories. Here is life itself, moving according to its own laws.