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Matthew 9:14-15 meaning
The parallel accounts of this event are found in Mark 2:18-20 and Luke 5:33-35.
Matthew tells us that after Jesus responded to the Pharisees' challenge, that the disciples of John [the Baptizer] came to Jesus (v 14). John was Jesus's cousin. His ministry was initially located in the Judean wilderness, northeast of the city of Jerusalem, near the Jordan River. He lived a rugged lifestyle very similar to the ascetic group known as the Essenes. The Essenes had a desert monastery in a wilderness area of the Jordan valley at Qumran, the sight of the discovery of the Dead Sea Scrolls in the 1940s.
John may have been affiliated with the Essenes. He was an ascetic, which means he lived a strict life of self-denial. He ate locusts and honey for food and wore camel hair for clothing (Matthew 3:4). John preached and baptized people, calling on them to "Repent, for the kingdom of heaven is at hand" (Matthew 3:2). Many came to be baptized by him and some followed him as disciples. Matthew last mentioned John when he told us that he had been taken into custody (most likely by the Sadducees in Jerusalem) while Jesus was spending forty days and forty nights fasting in the wilderness (Matthew 4:12). Now John's disciples made their way to Galilee, perhaps because they relocated there to be further away from their enemies in Jerusalem.
John's disciples ask Jesus, "Why do we and the Pharisees fast, but Your disciples do not fast?" (v 14).
Fasting was seen as a practice that righteous people did. The intent of fasting was to forego a secondary good (like food) to become closer to the greatest Good (God). In the Jewish culture, it was widely assumed that if a person fasted, he was righteous; and if a person was righteous, he would fast. The contraries to these assumptions were also accepted. If a person did not fast, he was unrighteous; and if a person was unrighteous, he wouldn't fast.
Their question was in some respects similar to the question the Pharisees just asked Jesus's disciples in Matthew's home (Matthew 9:11). Both questions challenge the behavior of Jesus and His disciples, which do not align with the cultural standards for righteous behavior among the religiously observant in Judea.
The tone in which John's disciples asked their question is not clear. John's disciples may have come to Jesus in a spirit of humble curiosity, or jealous envy. It might have been different than the self-righteous tone of condemnation used by the opposing Pharisees when they approached Jesus's disciples, or it might have been similar.
If the disciples of John came with a spirit of honest curiosity, they are seeking to reconcile an apparent contradiction. In essence, they were asking Him, "Righteous people (like us and the Pharisees) fast, we believe You and Your disciples are righteous, but yet Your disciples do not fast (v 14). Can you please explain this to us?" This view could be supported by the observation that Jesus' response to them appears to be milder than His response to the Pharisees.
On the other hand, John's disciples could have been asking their question out of self-righteous jealousy as the Pharisees did. "Why do we [who are righteous] and the Pharisees [who are perceived as righteous] fast, but Your disciples [and perhaps by extension—You, Yourself, Jesus] do not fast? (v 14). In other words, "If You are so righteous, why do You not perform the acts of the righteous, as we do?" If this was in fact, the tone in which they asked their question, it would be reasonable to speculate that after the Pharisees were unable to sow doubt among Jesus's disciples because of His response, they came to John's disciples and were able to plant sufficient doubt among them that they would challenge Jesus.
If they were in fact antagonistic in their asking, Jesus's milder response to them might be explained by His respect for John and a realization that He is speaking to someone who is being manipulated.
In either case, Jesus spoke to them by a parable and said, "The attendants of the bridegroom cannot mourn as long as the bridegroom is with them, can they?" (v 15). The answer to this rhetorical question is "No. The friends of the bridegroom do not mourn while he is with them." A bridegroom is a man full of happiness who is celebrating a joyous occasion. To celebrate, the bridegroom surrounds himself with friends who attend him at the wedding feast. These attendants honor him by celebrating with the bridegroom. It would be improper for the guests of the bridegroom to say, "We have chosen this as a time to fast" and refuse to participate in the celebration. In this parable, Jesus is the bridegroom. His disciples are the attendants of the bridegroom (v 15). And they are celebrating together. Therefore, they are joyfully feasting with Him instead of fasting and putting on a face of mourning.
"But the days will come," Jesus continues, "when the bridegroom is taken away from them, and then they will fast" (v 15). There will be a time for Jesus' disciples to fast. But it is not now, Jesus tells the disciples of John. That time will come when Jesus is taken away from them and no longer with them (v 15). The phrase taken away from them is either an allusion to His crucifixion and death, or more likely His ascension into heaven. When Jesus is no longer physically present with His disciples, then will come the days for His followers to fast (v 15).