"Then some of His disciples said among themselves, 'What is this that He says to us?'" (John 16:17). They questioned one another, likely whispering, as to the meaning of Jesus' prior statement. "We do not know what He is saying" (John 16:18). Truly, they are ignorant at this time, and they acknowledge such among themselves. However, they are reluctant to ask Jesus about the matter.
"Now Jesus knew that they desired to ask Him, and He said to them, 'Are you inquiring among yourselves about what I said, "A little while, and you will not see Me; and again a little while, and you will see Me"? Most assuredly, I say to you that you will weep and lament, but the world will rejoice; and you will be sorrowful, but your sorrow will be turned into joy. A woman, when she is in labor, has sorrow because her hour has come; but as soon as she has given birth to the child, she no longer remembers the anguish, for joy that a human being has been born into the world. Therefore you now have sorrow; but I will see you again and your heart will rejoice, and your joy no one will take from you. And in that day you will ask Me nothing. Most assuredly, I say to you, whatever you ask the Father in My name He will give you. Until now you have asked nothing in My name. Ask, and you will receive, that your joy may be full'" (John 16:19-24).
As predicted, the disciples did weep and lament because of Jesus' death (e.g., Mark 16:10; Luke 24:17; John 20:11), but their sorrow was transformed into joy upon learning of His resurrection (cf. Matt. 28:8). The world did rejoice at His death, thinking that the One who had condemned their ways would no longer bother them. Jesus does not directly explain the phrase His disciples are struggling to understand. Instead, He chose to allow subsequent events to make His meaning clear. In a couple months, much of what currently seemed incomprehensible to them would be crystal clear. Ultimately, His death, which initially produced great mourning, would become the factor that produced the greatest joy since it is through His death that forgiveness, peace, and a heavenly home are all made possible.
"A woman, when she is in labor, has sorrow because her hour has come; but as soon as she has given birth to the child, she no longer remembers the anguish, for joy that a human being has been born into the world" - This comparison is appropriate in a couple ways and is one that many can relate to personally. Although Jesus' death would be devastating to the disciples, their intense grief would not last long. They would not remember their "anguish" after Sunday because of the "joy" of seeing their Lord resurrected! When considering the imagery of this verse, it is interesting to note that Jesus is elsewhere referred to as "the firstborn from the dead" (Col. 1:18; Rev. 1:5).
"I will see you again and your heart will rejoice, and your joy no one will take from you" (cf. Luke 24:52,53). The resurrection of Christ brings a joyful hope to disciples that the world cannot take. In this regard, joy is much like salvation in that no one can take it from us. However, we can, through negligence and disbelief, give up both of these precious spiritual gifts.
The lives of the apostles after Pentecost aptly prove that they were fully convinced of Jesus' resurrection. The threats of wicked men and the persecutions they endured did not shake their faith or undermine their hope. Before Jesus' death, their faith was weak and wavering, but after His resurrection their faith was solid and strong.
"And in that day you will ask Me nothing" - The mysteries that currently perplexed the apostles would be fully explained and made clear through the Holy Spirit. Thus, there would be no need for them to ask Jesus anything. "Most assuredly, I say to you, whatever you ask the Father in My name He will give you" - During Jesus' ministry, the apostles had asked Him numerous questions. However, since Jesus was about to depart, this was about to change. They would not continue directing their inquiries toward Jesus but toward the Father in Jesus' name.
"Until now you have asked nothing in My name. Ask, and you will receive, that you joy may be full" - Jesus has set forth the conditions of their prayers in this context. They are to: (1) ask, (2) ask the Father, and (3) ask the Father in the name of Christ (i.e., by Jesus' authority). There is nothing in the New Testament that suggests that the above guidelines for prayer have changed. Christians today should likewise ask the Father by the authority of Jesus.