John 16:16-24 (ESV Strong’s Bible)
16 “A little while, and you will see me no longer; and again a little while, and you will see me.”
Jesus since chapter 15:18 until 16:16, has been telling His disciples that they will face persecutions for their faith. He is been preparing them and telling them to expect it. In verse 16 above, Jesus repeats what He has told them since chapter 7:33 and also in 14:19 that in a little while He will be gone and again in a little while He will be back. Jesus here is clearly reffering to His cruxifiction. The seeing him again can refer to either His resurrection or His second coming. Either of the events will bring Joy to the disciples.
17 So some of his disciples said to one another, “What is this that he says to us, A little while, and you will not see me, and again a little while, and you will see me’; and, because I am going to the Father’?” 18 So they were saying, “What does he mean by ‘a little while’? We do not know what he is talking about.”
The statement Jesus made confused His disciples, so they started asking each other what he meant.
19 Jesus knew that they wanted to ask him, so he said to them, “Is this what you are asking yourselves, what I meant by saying, ‘A little while and you will not see me, and again a little while and you will see me’?
Jesus, showing that He is God in a human form, He knew what they were asking themselves since He knows what is in men (John 2:25). Jesus told them what they wanted to ask him but were not doing it.
20 Truly, truly, I say to you, you will weep and lament, but the world will rejoice. You will be sorrowful, but your sorrow will turn into joy. 21 When a woman is giving birth, she has sorrow because her hour has come, but when she has delivered the baby, she no longer remembers the anguish, for joy that a human being has been born into the world. 22 So also you have sorrow now, but I will see you again, and your hearts will rejoice, and no one will take your joy from you.
Jesus in answering the question, He again tells them that they will cry and mourn while the world rejoices. This in my view, Jesus was reffering to when He has been killed, the world will rejoice because they would have finally gotten rid of him but the disciples will cry and mourn his death. Jesus then tells them that their crying and their mourning will turn into joy. He uses an example of a woman who is in labour pains. Jesus says just like when a woman gives birth, she goes through pain but when the child is born, she forgets the pain and rejoices. He says the same thing will happen to the disciples. They will cry and mourn for now but they will rejoice later when He sees them again. This will bring them joy that no one can take away. Again this could mean resurrection or the second coming. Either of these events will bring joy to the disciples.
23 In that day you will ask nothing of me. Truly, truly, I say to you, whatever you ask of the Father in my name, he will give it to you. 24 Until now you have asked nothing in my name. Ask, and you will receive, that your joy may be full.
Jesus then tells them that on that day when they see Him again, they will not ask him for anything but they will ask God directly in His name. When they see him again, they will be in a position to ask God directly anything in his name. Jesus told them that until that point, they had asked nothing from God in His name, but on that day when they see Him again, they must ask and they will recieve and that, will bring them full joy.
Something important to note here is that the word “ask” in verse 23 when reffering to Jesus is not the same word “ask” when Jesus reffers to asking God. When Jesus refers to asking himself, the Greek word used for the word ask means more of an inquiry and the Greek word used for the second ask is more of a request.