“weep and mourn” combines the thoughts of a very deep grief and an outward expression of that grief (Luke 23:27, John 20:11). Both of these words are used of the loud lamentations found in the east. They were even then filled with sorrow and would be for quite some time. Even their sleeping in Gethsemane was because of their exhaustion from their sorrow (Luke 22:45). Their weeping and mourning was for him because they loved Him and they would be feeling His pain in the hours ahead; and it also was for themselves, because of their own loss and the anxieties they had about what was going to happen to them after He was gone. They had left everything to follow Him (Luke 5:11) and now He was leaving them. No wonder they were filled with grief!

Luke 23:27  A large number of people followed him, including women who mourned and wailed for him.

John 20:11  but Mary stood outside the tomb crying. As she wept, she bent over to look into the tomb

Luke 22:45  When he rose from prayer and went back to the disciples, he found them asleep, exhausted from sorrow.

Luke 5:11  So they pulled their boats up on shore, left everything and followed him.

There is an emphatic contrast between “you” and “the world” and thus between the way the world views the death of Jesus and the view of those who love Him. His enemies will certainly rejoice over His death (Luke 22:5). The world has a much different view of things than we do. We should not be surprised when they gloat and rejoice over the things that cause us to weep and mourn (Rev 11:10). Can you think of any present-day examples? (Sin would be one example.)

Luke 22:5  They were delighted and agreed to give him money.

Revelation 11:10  The inhabitants of the earth will gloat over them and will celebrate by sending each other gifts, because these two prophets had tormented those who live on earth.

“But” indicates that there is something unexpected in the joy the disciples will experience. Who could guess that such a tragedy could become so great a triumph?

The disciples’ “grief will turn to joy.” It is probably significant that He does not say that their sorrow will be “replaced” by joy. It will turn into joy. The very thing which causes them such sorrow (the cross) will later become their source of joy because of the resurrection. This corresponds to the illustration which follows in the next verse.

Notice the change from sorrow to joy that actually happened to them: (John 20:14-16, Matt 28:8, John 20:20, Luke 24:41). Praise God that His promises are still in effect today (Psalms 126:5, Rom 8:28)! Have you had anything in your life which caused you to weep and mourn but which God later turned into a source of rejoicing for you?

John 20:14-16  At this, she turned round and saw Jesus standing there, but she did not realise that it was Jesus.  “Woman,” he said, “why are you crying? Who is it you are looking for?” Thinking he was the gardener, she said, “Sir, if you have carried him away, tell me where you have put him, and I will get him.”  Jesus said to her, “Mary.” She turned towards him and cried out in Aramaic, “Rabboni!” (which means Teacher).

Matthew 28:8  So the women hurried away from the tomb, afraid yet filled with joy, and ran to tell his disciples.

John 20:20  After he said this, he showed them his hands and side. The disciples were overjoyed when they saw the Lord.

Luke 24:41  And while they still did not believe it because of joy and amazement, he asked them, “Do you have anything here to eat?”

Psalms 126:5  Those who sow in tears will reap with songs of joy.

Romans 8:28  And we know that in all things God works for the good of those who love him, who have been called according to his purpose.