Jn. 16:18. So they were saying: what is this that He says: "a little while"? We do not know what He is saying.
Therefore one might well wonder how they did not understand His words. Most likely, the grief that had taken hold of their soul was erasing from their memory what was being said, or a lack of comprehension came upon them due to the obscurity of the words themselves. And so a certain contradiction appeared to them in the words of Jesus: "If we shall see You, then where are You going? But if You are going away, then how shall we see You?" This seemed to them a riddle.
Jn. 16:19. Jesus, having understood that they wanted to ask Him, said to them: Are you inquiring among yourselves about what I said: "In a little while you will not see Me, and again in a little while you will see Me"?
The Lord saw that the disciples, burdened with sorrow, did not fully understand His words; therefore He offers them a clearer teaching about His death, so that, having grown accustomed to the words and deeds, they might bear it courageously.
Jn. 16:20. Truly, truly, I say to you: you will weep and lament, but the world will rejoice; you will be sorrowful, but your sorrow will be turned into joy.
"You," He says, "will weep and lament that I will die on the Cross, while the world will rejoice, that is, the Jews, who think in worldly terms, will rejoice that they have destroyed Me, their enemy; but your sorrow will be turned into joy, while the joy of the Jews, on the contrary, will be turned into sorrow for them, when after the Resurrection My name will be glorified."
You can understand the joy of the world not as the joy of the Jews, who rejoiced at the killing of the Lord, but as the salvation of the world, so that in these words the meaning will be as follows: you will be sorrowful, but these sufferings of Mine, over which you grieve, will be the joy of the whole world and its salvation.
Jn. 16:21. A woman, when she gives birth, endures sorrow, because her hour has come; but when she has brought forth the child, she no longer remembers the anguish, for joy that a human being has been born into the world.
Then He brings an ordinary example of a woman and childbirth. This comparison was also used by the prophets, using the severity of labor pains to denote the highest degree of sorrow. He speaks as if to say: "Sorrows will overtake you, like the pains of birth; but the pain is the cause of the birth."
At the same time He confirms the teaching about the resurrection and shows that to die is similar to coming out of the mother's womb into the light. Do not marvel, then, that you must attain joy through such sorrow. For a mother, too, through grief and pain attains to becoming a mother. Here He hints at something mysterious, namely: that He destroyed the pangs and death and brought it about that a new Man was born, one no longer subject to corruption, no longer subject to death, who is the Lord Himself. For look, He did not say "the woman no longer remembers her anguish because a child has been born to her," but — "because a man has been born into the world." He did not say this without purpose, but in order to hint enigmatically and covertly that He Himself is the Man who was born not for Hades, which travailed with Him, but for the world. For through the resurrection a new and incorruptible Man was born for us — Jesus Christ, our God.
So then, the example of a woman giving birth does not require full adaptation to the events of Christ, but only aims to show that sorrow is temporary, and that from these pains the benefit is great, and that the resurrection gives birth to life and a new existence. Everything else in the comparison has no application, and rightly so. For this is a parable, and a parable, if it is preserved in all its parts, is no longer a parable, but the very thing that it depicts.
Jn. 16:22. So you too now have sorrow; but I will see you again, and your heart will rejoice, and no one will take your joy from you;
So here too, by the pangs of birth we understand the sorrow of the apostles, and by the joy – their consolation after the resurrection, and again by the loosing of the pangs – the destruction of Hades, and by the birth – the resurrection of the Firstborn from the dead. But we no longer understand by the mother – Hades; for it was not Hades that rejoiced, but the apostles rejoiced, and they rejoiced with such joy that no one took from them. For when they were wronged, when they were dishonored for the name of Christ, even then they rejoiced (Acts 5:41).
By the words "your joy no one will take away," He also shows that He will no longer die, but, being ever alive, will grant them inexhaustible joy.
Jn. 16:23. And in that day you shall ask Me nothing.
"When," He says, "I rise again, and then the Comforter comes to you and guides you into all truth, then you will not ask Me anything, as, for example, you previously asked: 'Where are You going?' (John 14:5), 'Show us the Father' (John 14:8). For by the power of the Spirit you will know all things." Or "ask" is used in place of "request, demand."
Jn. 16:23. Truly, truly, I say to you: whatever you ask the Father in My name, He will give you.
So, when I, after the resurrection from the dead, send you the Comforter, then you will no longer ask Me, that is, you will not need My mediation, but it will be enough for you to utter My name in order to receive what you desire from the Father.
So here He shows the power of His name. Since they will not see Him and will not ask Him, but will only invoke His name, and He will perform such deeds.
Jn. 16:24. Ask, and ye shall receive, that your joy may be full.
"Until now you have asked nothing in My name," but from now on "ask, and" you will certainly "receive." Therefore it is more beneficial that I die; for from now on you will have greater boldness before My Father. Although I will be separated from you, do not think that you have been abandoned by Me; for My separation from you will give you greater boldness, and your joy will then be most complete, when you receive everything you ask for.
Observe then: he who asks in the name of Christ receives. But of those who desire worldly and soul-harming things, no one asks in the name of Christ, and therefore does not receive. For the name of Christ is Divine and salvific. But if someone asks for something ruinous to the soul, shall we really say that he asks in the name of the Savior?
Jn. 16:25. Until now I have spoken to you in figures of speech; but the time is coming when I will no longer speak to you in figures of speech, but will tell you plainly about the Father.
A parable is a speech that explains a certain subject indirectly, covertly, and comparatively. Since the Lord spoke many things covertly, and the discourse about the woman and childbirth was also parabolic, He says: "Until now I have spoken to you in parables; but the time is coming when I will no longer speak to you in parables, but will tell you plainly about the Father."
For after the resurrection, having shown Himself alive, "over the course of forty days" He imparted to them the most mystical and detailed knowledge about the Father (Acts 1:3). But before this they thought that God was His Father in the same way as He is ours, by grace.