Superiority of the New

Setting and Overview
In the preceding verses, Matthew used the narrative of his own call and the subsequent banquet that he threw for Jesus to communicate Jesus’ message about discipleship and of changing expectations. As we come to Matthew 9:14-17, we once again have a group coming to bring a complaint related to banquet and Jesus responding to the complaint with teaching, but we see several things that are different as well. Before it was the Pharisees bringing the objection, here the focus is on John’s disciples. Before it was a complaint brought to the disciples about Jesus, now it is a complaint brought to Jesus about the disciples. Before, it was the nature of the guests at the party that brought out the conflict, here it is the party itself. Despite those differences, much still remains the same. Jesus is still challenging expectations, still showing how He fulfills the Old Testament, and still providing a radical picture of what it means to be one of His disciples.
Exposition
John the Baptist’s disciples seem like unlikely allies with the Pharisees, but they find some common ground in taking issue with Jesus’ disciples. Both groups likely followed the tradition of fasting on Mondays and Thursdays, although the Old Testament only commanded fasting on Day of Atonement. John himself is not shown as having any jealousy of Jesus (John 3:26-30) but perhaps his disciples feel differently (especially if he is now in jail and they resent the lifestyle of Jesus’ disciples versus their own - Matthew 11:18-19.)
In referring to Himself as the bridegroom, John’s disciples would have likely picked up on the Messianic claim, especially as it connected with John’s own statements (John 3:27-28), but the application goes even farther. In the Old Testament, God Himself is presented as the bridegroom of adulterous and rebellious Israel (Jeremiah, 2:1-3, 2:20, 24-25, 3:20, Hosea 2:2-13.) Furthermore, despite Israel’s wandering, God declares that He will pursue and bring back Israel (Hosea 2:14-23, 3:1-5, Isaiah 62:1-5.) Fasting should be done with a sincere and humble spirit, mourning sinfulness and expressing desire to draw nearer to God (Isaiah 58:4-7, Joel 2:12-14.) Now that Jesus has arrived, this period should not be one marked by mourning by His followers, therefore they don’t fast while He is with them.
Jesus also uses this opportunity to make a larger point about Judaism and its traditional practices. In the first analogy, He compares it to a garment with a hole. If you take a new piece of stronger, unshrunk cloth, and try to patch it onto the garment, it will only tear the old garment worse since the old garment will not be strong enough to handle the pulling. In the second analogy, He compares it to old wineskins. If you try to pour wine into old wineskins which have been stretched and weakened, then when the wine ferments and expands, it will tear the wineskins and the wine will be lost. Through both, Jesus is showing that the old practices of Judaism have weaknesses and holes, and they cannot contain His new revelation. To try to understand all that He is teaching within the structure of traditional Judaism, or to even try to “patch up” Judaism with some snippets of new practices will not work. His new revelation must be understood within an entirely new way, one which has continuity with the Old Testament, but cannot be contained by it.

Examination and Application
On this side of the cross, we do not need to mourn as the Jews once did, but that doesn’t mean that there is no place for fasting (Acts 13-14.) We can rejoice that Jesus has come and look forward to the promise that He will present the Church to Himself as glorious (Ephesians 5:26-27, 1:4, Revelation 19:6-8) but we should also lament our tendency to turn away from pure devotion (II Corinthians 11:2-3.) We should fast as a natural expression of our desperation to grow closer to Him when nothing else can satisfy us. We should also fast when we recognize that we have allowed earthly satisfactions to compete with the satisfaction that we have in Him and we need to remove any distractions that would pull us away from seeking Him fully.