John's disciples saw a difference they could not explain. They fasted often, as the Pharisees did, yet the followers of Jesus, the One their own teacher had pointed to, did not. Barnes thinks it "probable that this question was put to him when John was in prison," and that his grieving disciples kept days of fasting. In Barnes' words, "they wondered that the followers of Jesus did not join with them in lamenting the captivity" of John. Gill reads it differently: he says it was asked "not so much by way of inquiry, as reproof," and gives two possible occasions: John's disciples were either offended at hearing "of the great entertainment made at Matthew's house," or "set on by the Pharisees." Their question presses Jesus to explain why His followers were not keeping the practice that both John's circle and the Pharisees counted as part of a serious life with God.

Jesus answered with a question of His own: "Can the children of the bridechamber mourn, as long as the bridegroom is with them?" (Matthew 9:15). He added that "the days will come, when the bridegroom shall be taken from them, and then shall they fast." He then gave two pictures: no one sews new cloth onto an old garment, and no one puts new wine into old bottles (Matthew 9:16-17). No further reply from John's disciples is recorded.

The law of Moses commanded one yearly day when Israel would "afflict your souls," the Day of Atonement (Leviticus 16:29), but the frequent fasts mentioned here went beyond that. Gill says these were "private fasts" kept "according to the traditions of the elders," and notes the Pharisees fasted "twice a week, on Monday and Thursday," besides fasts for droughts and other calamities. The Pharisee in Jesus' parable boasts, "I fast twice in the week" (Luke 18:12).

John the Baptist had been "cast into prison" (Matthew 4:12). If, as Barnes suggests, this question came while he was there, his disciples' fasting would have been an expression of sorrow. In Mark's account the question is put more generally (Mark 2:18), and in Luke it is asked by the Pharisees and their scribes (Luke 5:30, 33).

This question opens the way for Jesus to say who He is. John's disciples asked about a religious practice; Jesus answered by calling Himself "the bridegroom." John himself had already used that picture, saying he was only "the friend of the bridegroom" (John 3:29), a link Gill points out. The difference in practice came down to a difference in the moment: the Bridegroom had arrived.

Jesus did not say fasting was wrong. He said it would return "when the bridegroom shall be taken from them" (Matthew 9:15). Matthew Henry puts it simply: "When he is with them, all is well. The presence of the sun makes day, and its absence produces night." The practice had to fit the moment: mourning belongs to the Bridegroom's absence, not His presence (Matthew 9:15).