When examining the moment in Matthew 9:14 where John’s disciples questioned Jesus about fasting, it’s helpful to remember the historical context.
At this moment in time Jesus’ cousin, John the Baptist, languished in prison as punishment for doing pretty much the same things (minus the miracles) that Jesus was doing. John’s ministry had emphasized obvious elements of asceticism, including the traditional practice of fasting two days a week. His disciples mimicked that practice—considered a basic part of holy living—plus they fasted as a sign of mourning because their beloved leader had been cruelly taken from them.
Meanwhile, Jesus was favored with abundance and popularity. He moved about freely, working miracles, preaching and teaching, and challenging the religious elite. He carried on like he was oblivious to John’s predicament, eating and drinking as if life were a celebration. To John’s disciples, that seemed incongruent. If Jesus were indeed the Messiah—as John had seemed to declare—then it should’ve been natural for he and his disciples to fast as they did, including fasts in mourning over John’s imprisonment. It was an incongruence they couldn’t explain, so give them credit for asking Jesus about it instead of simply condemning him for it (as Pharisees did).
In that historical context, Jesus took time to help John’s disciples understand that both fasting and feasting were holy expressions. First, notice that Jesus didn’t condemn John’s followers for fasting; in fact, he acknowledged their expressions of mourning as appropriate in circumstances similar to theirs (see Matthew 9:15).
Next, Jesus pointed out that, unlike John’s followers who had been separated from their leader, his disciples were still in the presence of the, messianic “bridegroom”—a situation that warranted celebration, while it lasted. Emphasizing his point with parables of wine and cloth, Christ plainly explained to John’s disciples that fasting and feasting weren’t meant to be one-size-fits-all patches to place arbitrarily on anyone’s life. They were, and still are, tools meant to be applied in specific circumstances, to be used in the right times and places. In that way, both are suited to the lives of all holy followers of God.
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