16:1 “All this [the words about His own persecution and theirs] I have told you so that you will not go astray [stumble; to be caught off guard; Jesus wanted His followers to be ready for the difficult times to come; warning of persecution prepared them to face it].
16:2 They will put you out [expel; excommunication; loss of fellowship] of the synagogue [cf. Jn. 9:22; 12:42]; in fact, a time is coming when anyone who kills you will think [suppose] he is offering a service [priestly service] to God [cf. Acts 7:57—8:3; 22:3-4; 26:9-12 re: Saul of Taursus].
16:3 They will do such things [persecute, excommunicate, kill] because they have not known [ignorance; cf. 1 Tim. 1:13] the Father or me.
16:4 I have told [forewarned] you this [message concerning hatred and persecution], so that when [indicates the certainty of persecution] the time comes you will remember that I warned you. I did not tell you this at first because I [Jesus Himself had been their protection; He had deflected criticism and opposition away from disciples] was with you.
16:5 “Now I am going to him who sent me, yet none of you asks [what could have helped them realize that Jesus’ departure was for their good] me, ‘Where are you going?’
16:6 Because I have said these things, you are filled with grief.
16:7 But I tell you the truth: It is for your good [it is expedient; it is of an advantage; it is profitable] that I am going away. Unless I go away [Jesus’ presence on earth was limited to one place at one time], the Counselor [lives in every believer in the whole world] will not come to you; but if I go, I will send him to you.
16:8 When he comes, he will convict [cross-examine for purpose of refuting an opponent; expose the facts, convince someone of the truth, accuse, refute] the world of guilt in regard to  sin [step one is to convince people that they are guilty of sin; must know you are lost before you can be saved] and  righteousness [people need to know that they fall short of God’s standard of righteousness (Rom. 3:23); Holy Spirit legally convicts people of their sin, representing the righteous judgment of God] and  judgment [people must be convinced about the reality of a coming judgment]:
16:9 in regard to sin, because men do not believe [greatest sin is refusal to believe in Jesus (cf. Jn. 3:18)] in me;
16:10 in regard to righteousness [Spirit shows people that Christ alone provides the standard of God’s righteousness; Spirit shows the world the futility of self-righteousness and the inadequacy of works, rites, rituals, religion], because [Spirit would continue work of Jesus] I am going to the Father, where you can see me no longer;
16:11 and in regard to judgment [Spirit shows that through Jesus’ death and resurrection Satan has already been condemned; convicts us of our impending judgment if we fail to believe in Jesus], because the prince of this world now stands condemned.
16:12 “I have much more to say to you, more than you can now bear [grasp; understand; basic idea is that they cannot understand now; cf. Mk. 4:33].
16:13 But when he, the Spirit of truth, comes, he will guide [to show the way; the figure of a guide who introduces the traveler into an unknown country; the Spirit would expand the apostles’ partial understanding of Christ’s life and mission; cf. 2 Pet. 1:21; 1 Cor. 2:13; 2 Tim. 3:16] you into all truth [the truth about Jesus’ identity, the truth of His words and actions, the truth about all that was to happen to Jesus; cf. 1 Jn. 2:20]. He will not speak on his own [what the Holy Spirit speaks is consistent with what Jesus taught]; he will speak only what he hears, and he will tell you what is yet to come [the outworking of God’s redemptive purpose; insights given to the apostles regarding the Crucifixion, Resurrection, Ascension, and perhaps the second coming of Christ or the body of Christian truth and doctrine communicated by the apostles].
Note: You are never alone…
• when you live day to day. As a believer, the Holy Spirit lives in you. You can count on the Holy Spirit to help you face life with confidence.
• when you share your faith. You can count on the Holy Spirit to work in the lives of unbelievers and to convict them of their guilt before God.
• when you study God’s Word. You can count on the Holy Spirit to guide you as you study and seek to apply Christ’s truths in your life.
16:14 He will bring glory to me [even as Jesus brought glory to the Father; Spirit always points people to Jesus] by taking from what is mine and making it known [to proclaim; cf. Jn. 15:26] to you.
16:15 All that belongs to the Father is mine [unity between Father, Son, and Spirit]. That is why I said the Spirit will take from what is mine and make it known to you.
16:16 “In a little while [in a few hours] you will see me no more [refers to Jesus’ death], and then after a little while you will see me [refers to Jesus’ resurrection].”
16:17 Some of his disciples said to one another, “What does he mean by saying, ‘In a little while [in a few hours] you will see me no more [reference to His death], and then after a little while you will see me [reference to His resurrection],’ and ‘Because I am going to the Father’ [cf. John 16:10]?”
16:18 They kept asking, “What does he mean by ‘a little while’? We don’t understand [means “to see” and signifies perception and knowledge] what he is saying.”
16:19 Jesus saw [to know, perceive, understand] that they wanted to ask him about this, so he said to them, “Are you asking [implies search for something hidden] one another what I meant when I said, ‘In a little while you will see me no more, and then after a little while you will see me’?
16:20 I tell you the truth, you will weep and mourn [reference is to the loud wailing and lamentation that is the customary reaction to death in the Near East] while the world [people who opposed/hated Jesus] rejoices [because of death of “madman” or troublemaker]. You will grieve, but your grief will turn to joy [at the sight of their resurrected Lord].
16:21 [analogy] A woman giving birth to a child has pain because her time has come; but when her baby is born she forgets [joy of childbirth overshadowed memories of pain] the anguish [trouble (cf. 16:33)] because of her joy that a child is born into the world.
16:22 So with you: Now [at the present moment and over the next couple of days] is your time of grief, but I will see you again and you will rejoice [because they would see Jesus again], and no one will take away your joy [a permanent joy, unlike the fleeting joy of Jesus’ enemies; cf. Ps. 30:5b; Acts 5:41].
16:23 In that day [refers to the time subsequent to the day of Jesus’ resurrection; the time the Spirit would be available to teach them (cf. 16:12-15)] you will no longer ask [cf. Jn. 16:19; primarily means to ask by way of inquiry, and then by request; time would come when the disciples would not need to ask Jesus anymore questions] me anything [but instead the disciples could take their requests directly to the Father]. I tell you the truth, my Father will give you whatever [limited by “in His name”] you ask [to ask by way of petition; make requests directly to the Father, who would answer requests in Jesus’ name (cf. 14:13-14; 15:7)] in my name [requests that the believer knows Jesus would be pleased to answer and that are in accordance with the Father’s will].
Note: To ask or pray in Jesus’ name means…
• to acknowledge that He is the means of our access to God.
• to base our requests on who Jesus is and on what He has done for us.
• to ask on His authority and in keeping with His will and character.
16:24 Until now you have not asked for anything in my name. Ask and you will receive, and your joy [answered prayer brings joy] will be complete [cf. 1 Jn. 5:13-15].
16:25 “Though I have been speaking [refers to what Jesus had taught in the final hours before His crucifixion and perhaps the things He taught throughout His earthly ministry] figuratively [or in parables, metaphors, similes; cf. 16:12-13], a time is coming when I will no longer use this kind of language but will tell you [through the Holy Spirit; cf. 16:13-15] plainly [clear and fresh understanding] about my Father.
16:26 In that day you will ask [direct, personal access to God] in my name. I am not saying that I will ask the Father on [concerning] your behalf [instead, disciples would go straight to God, asking in Jesus’ name; cf. Heb. 4:16].
16:27 No, the Father himself loves you because you have loved me [the Son whom the Father dearly loves] and have believed that I came from God.
16:28 [description of Jesus’ entire mission] I came from the Father [preexistence] and entered the world [incarnation; to secure salvation for human beings]; now I am leaving the world and going back to the Father [resurrection and ascension; cf. Jn. 17:5].”
16:29 Then Jesus’ disciples said, “Now you are speaking clearly and without figures of speech.
16:30 Now we can see that you know all things and that you do not even need to have anyone ask you questions. This makes us believe that you came from God.”
16:31 “You believe at last!” Jesus answered.
16:32 “But a time is coming, and has come, when you will be scattered, each to his own home. You will leave [forsake] me all alone. Yet I am not alone, for my Father is with me.
16:33 “I have told you these things [the things shared in the hours before arrest and crucifixion], so that in me you may have peace. In this world you will have trouble [tribulation, persecution, affliction]. But take heart [have courage, be courageous; be of good cheer]! I have overcome [military term; to conquer (perfect tense denotes abiding spiritual victory)] the world [Satan’s system that is opposed to God].”