The context for the Parable of the Cloth and the Wineskins begins in Luke 5:17, when a paralyzed man is brought to Christ. He recognizes the faith involved and tells him that his sins are forgiven (verses 18-20), a statement that the scribes and the Pharisees, of course, consider blasphemous (verse 21). They rightly understand that only God takes away sin, but they would not consider that the Man who was forgiving sin was God. In verses 22-25, Jesus gives proof that He had been given the power to forgive sins: The man had taken up his bed and was walking home.
After this incident, Jesus calls Levi, or Matthew, the tax collector (Luke 5:27), who becomes a disciple and subsequently prepares a feast in honor of Jesus (verses 28-29). In verse 30, the scribes and Pharisees object to His mingling with tax collectors and other sinners, but Jesus responds, “Those who are well don't need a physician, but those who are sick do. I have not come to call the righteous, but sinners to repentance” [New English Translation (NET)].
At this point, many translations insert a subheading about fasting, but the story continues. The Pharisees point out that John the Baptist's disciples made prayer and fasting a regular part of their lives, and they slip in the fact that their disciples did that as well (Luke 5:33). Then they contrast that with Christ's disciples, observing that they have a great penchant for eating and drinking. They imply that His disciples cannot really be serious about a holy life when all they do is have a good time, and in their minds, this reflects poorly on the Teacher. We know this because in Luke 7:34, Jesus quotes the Pharisees as saying that He—the Son of God—is a glutton and winebibber.
Jesus counters that it would be just as inappropriate for His disciples to fast at that time as it would be for the wedding party to fast when the bridegroom is with them (Luke 5:34-35). In other words, Christ's presence should be a cause for joy. Psalm 16:11 (NET) says, “I experience absolute joy in Your presence; You always give Me sheer delight.” Yes, Jesus was also a man of sorrow and acquainted with grief, but there was every reason for His disciples to be cheerful when they were in His presence. They had no need to draw closer to God through fasting because He was with them.
His example is clear enough on its own, except that a well-known Messianic prophecy speaks of Israel's God as her Bridegroom (Isaiah 62:5). He was already on the Pharisees' bad list for telling a man that his sins were forgiven, and now He follows that up by referring to Himself as the Bridegroom!
Luke 5:35 is pivotal when it comes to understanding the parable that follows: “But the days will come when the bridegroom will be taken away from them; then they will fast in those days.” We know how that played out. He was “taken away” first through His crucifixion and then later through His ascension. Jesus being “taken away,” however, resulted in a tremendous blessing.
David C. Grabbe
Clothing, Wineskins, and Wine