Continuing a Bible study of the Gospels:
(John 16:1) "These things I have spoken to you that you should not be offended."
In the last chapter, Jesus had told His disciples of His love for them, how He desired that they continue in that love and love one another as He had loved them. He told them that they would be persecuted for His name's sake, but that if they stayed connected with Him as branches to a vine, He would send His Holy Spirit to guide them in all truth. He now told them that He had told them all those things that they not be offended or discouraged by any persecution they might receive. By knowing that it would occur, they need not be taken aback and dissuaded from continuing their work.
(2) "They shall put you out of the synagogues; yes, the time is coming that whoever kills you will think that he does God service."
Jesus told His disciples that they could expect to be put out of the synagogues, and that the time was coming when someone could kill them thinking they were doing a good service to God. Just as the Pharisees had accused Jesus of blasphemy, they would be likewise accused and condemned as blasphemers.
(3) "And these things they will do to you because they have not known the Father nor Me."
Jesus explained they would do those things to them because they had not known God and His word nor their Messiah, Jesus Christ.
(4) "But these things I have told you that when the time shall come, you may remember that I told you of them. And these things I did not say to you at the beginning because I was with you."
Jesus again told them that He had told them these things that they not be shocked when persecution happened, and that they remember Jesus had forewarned them. He explained that He had not told them these things in the beginning because He was with them. He was the target of the persecution, but now that He would no longer be with them, they would be the targets because of their relationship with Him.
(5) "But now I go My way to Him who sent Me, and none of you asks Me, 'Where are You going?'"
Jesus said He was now going His way back to His Father, and none of them were asking Him where He was going. Peter and Thomas had asked Him before (John 13:36 and 14:5), but they had not pursued it to the point of understanding truly where He was going and why. And now none of them asked.
(6) "But because I have said these things to you, sorrow has filled your heart."
They did not ask Him for further explanation because they were too deep in sorrow that He was leaving them.
(7) "Nevertheless, I tell you the truth; it is expedient for you that I go away, for if I do not go away, the Comforter will not come to you, but if I depart, I will send Him to you."
The disciples had not asked Jesus to explain because they had yielded to their grief, but He wanted to explain anyway. He said it was good for them that He go away. If He didn't go away, His Holy Spirit could not come to them. However, they might wonder why the Holy Spirit would be better than having Jesus Himself. The Holy Spirit was of Jesus, of God, and could fill all of them at once, and could inhabit others who became followers of Jesus. Therefore He could be in many places at once, rather than just one human Jesus in one place at a time. His Holy Spirit would be with them always. Once He left them, He could send His Spirit to them.
(8) "And when He has come, He will reprove the world of sin, and of righteousness and of judgment."
The meaning of the original word "elegcho" which was translated as "reprove" also means "convict" or "convince" which is probably the best sense here. When the Holy Spirit came, He would convict the people of their sins, and of righteousness and judgment, as He explains:
(9) "Of sin, because they do not believe in Me;"
First, the Holy Spirit would convict people of their sins, primarily the sin of rejecting Jesus and not believing in Him.
(10) "Of righteousness, because I go to the Father, and you see Me no more;"
The Holy Spirit would convince people of Jesus's righteousness when they see He was resurrected back to heaven and sent back His Spirit of Truth that would guide them in righteousness and remind them of Jesus's words.
(11) "Of judgment, because the prince of this world is judged."
The people would be convinced of Jesus's righteous judgment in judging and overcoming Satan. The Holy Spirit would open the eyes and hearts of man to reveal what they had done to the Savior of the world, to the fact that Jesus was indeed from the Holy God in heaven, and that He was the righteous judge against the actions of Satan demonstrated in people. As Adam and Eve ate of the forbidden fruit and came to know good and evil (Genesis 3:22), the Holy Spirit would convict people of good and evil and would direct them to the path of their salvation through Jesus Christ from their condemned states which were the result of Adam's fall.
(12) "I have yet many things to say to you, but you cannot bear them now. (13) However, when He, the Spirit of truth, has come, He will guide you into all truth, for He shall not speak of Himself, but whatever He shall hear, He shall speak, and He will show you things to come."
Jesus said He had many more things to tell His disciples, but they would not be able to bear and understand them at that time. However, when the Holy Spirit came, after they had witnessed Jesus's death and resurrection and ascension back to heaven, they would be better able to understand the mysteries of Jesus's Gospel of salvation. The Holy Spirit of truth would tell them the things Jesus wanted them to know because He spoke not from Himself, but directly from Jesus, and He would tell them of things to come.
(14) "He shall glorify Me for He shall receive of Mine and shall show to you."
The Holy Spirit's purpose was to glorify Jesus by taking what was directly from Jesus, His commission and instruction, and communicating those things to Jesus's followers.
(15) "All things that the Father has are mine; therefore I said that He will take of Mine and will show to you."
Jesus asserted to His disciples His authority to give and receive everything as given and received by His Father. He had every nature and being of His Father. He and His Father were one, so He had the full authority and pleasure of God to tell the Holy Spirit how to communicate with and guide His followers.
(16) "A little while and you shall not see Me, and again, a little while and you shall see Me because I go to the Father."
Jesus told His disciples that in a little while they would no longer see Him, because of course, He was about to die. However, a little while after that, they would see Him again when He was risen from the dead, and that was possible because He was resurrected to ascend back to His Father in heaven.
(17) Then said of His disciples among themselves, "What is this that He says to us, 'A little while and you shall not see Me, and again, a little while and you shall see Me'? And 'because I go to the Father'?"
His disciples discussed among themselves what the meaning of Jesus's words could be.
(18) They said therefore, "What is this that He says, 'A little while'? We cannot tell what He says."
The disciples surely knew that Jesus was about to die soon, in a little while, but that they would see Him again in a little while? That made no sense to them, so they didn't understand what He meant.
(19) Now Jesus knew that they were desirous to ask Him, and said to them, "Do you inquire 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’?"
Jesus knew what His disciples were discussing among themselves and that they wanted to know what He meant, so He asked them directly if they were discussing His words to them, "A little while, and you will not see Me; and again, a little while and you will see Me.'"
(20) "Verily, verily, I say to you that you shall weep and lament, but the world shall rejoice, and you shall be sorrowful, but your sorrow shall be turned into joy."
Jesus told them that they would most assuredly weep and lament when they saw Him crucified and laid in a tomb, but the world would rejoice because they thought they had killed and eliminated Jesus. The disciples would remain sorrowful after His death, but their sorrow would be turned to joy when they saw that He had defeated death and rose again.
(21) "A woman, when she is in labor, has sorrow because her hour has come, but as soon as she has delivered the child, she no longer remembers the anguish, for joy that a man is born into the world."
Jesus said that just as a woman in labor had much pain and sorrow, as soon as she had delivered that new life into the world, she no longer remembered all the pain and anguish because of the joy she had for her child.
(22) "And you now therefore have sorrow, but I will see you again, and your heart shall rejoice, and your joy no man can take from you."
Jesus confirmed that He knew they had sorrow at that time, but He would see them again and then their hearts would rejoice and would be filled with joy that no man would be able to take from them from that point forward when they began to understand more fully Jesus's purpose on earth and the fulfillment of that purpose.
(23) "And in that day you shall ask Me nothing. Verily, verily, I say to you, whatever you ask the Father in My name, He will give you."
Jesus said that in that day, they would have no need to ask Him anything. For one, they would have a more complete understanding of all that Jesus had said; and they would then have direct access to the Father to ask anything of Him in the name of Jesus, because through Him the way was opened to the Father. And whatever they asked in Jesus's name, because of Jesus and for His purpose, the Father would give to them.
(24) "Until now you have asked nothing in My name; ask, and you shall receive, that your joy may be full."
Jesus explained that up to that point, they had not asked anything in His name, rather, they had asked Him directly. He would no longer be there to ask directly, but anything they asked in His name, because of Him and for His purposes, they would receive, and that was to increase their joy and confidence in their work.
(25) "These things I have spoken to you in proverbs, but the time comes when I shall no more speak to you in proverbs, but I shall show you plainly of the Father."
Jesus said He had up to that point spoken to them in proverbs or parables, in figurative language. However, the time was coming when He would speak to them plainly through His Holy Spirit about the nature and purposes of the Father.
(26) "At that day, you shall ask in My name, and I do not say to you that I will pray to the Father for you, (27) For the Father Himself loves you because you have loved Me and have believed that I came out from God."
At that time, they would ask the Father directly in Jesus's name. Before then, they did not have direct access to the Father, but Jesus would pray to the Father for them. However, because of His sacrifice and atonement for their sins, they would then have the ability to go directly to the Father because they had loved and believed in Jesus for their redemption from sin, knowing He came directly from God.
(28) "I came forth from the Father and have come into the world; again, I leave the world and go to the Father."
Jesus had come directly from Father God into the world, and He would leave the world and go back to His Father again.
(29) His disciples said to Him, "Lo, now You speak plainly, and speak no proverb. (30) Now we are sure that You know all things and have no need that any man should ask You; by this, we believe that You came forth from God."
Jesus's disciples told Him that He was then talking plainly so that they understood Him. They were sure that He knew all things, even men's very thoughts, so that there was no need for them to ask Him anything for He already knew what they wanted. They could plainly see that He had come from God.
(31) Jesus answered them, "Do you now believe? (32) Behold, the hour comes, yes, is now come, that you shall be scattered, every man to his own and shall leave Me alone; and yet, I am not alone because the Father is with Me."
I believe Jesus's point was to question whether or not they truly believed, because as much as they thought they had strong faith, the time was at hand when they would all scatter and leave Him alone. Yet He would not really be alone as His Father would be with Him. Or it could have been Jesus was suggesting that they now believed, but soon they wouldn't.
(33) "These things I have spoken to you that in Me you might have peace. In the world you shall have tribulation, but be of good cheer; I have overcome the world."
Jesus had told His disciples all those things that they not be taken by surprise. They might have peace when they unfolded because they knew the truth and the outcome. They would have tribulation and persecution in the world, but Jesus had overcome the world and death. What a beautiful end to this chapter and a blessing of great encouragement to His disciples!