Jesus has said (16:7) that it is for their good that he is leaving them. In the first half of the chapter that “good” has been explained in terms of the gift of the Counsellor, the Holy Spirit. In this passage the “good” that becomes ours is joy – a joy that no one can take away (v.22), and a joy that is complete (v.24). A joy we can know even in this world where we will know trouble (v.33).
As the passage opens (vv.16-18) we are reminded of the disciples’ lack of understanding at that time. Jesus knows they face a rollercoaster ride in the coming few days: they will grieve at his death, which will seem a total tragedy. Their grief will be deep, but brief, turning to joy (v.20). The illustration of childbirth is helpful in showing how the pain and the joy are connected – the thing that caused their pain and sorrow will actually become the reason for their joy. Seeing him again (v.22) after his resurrection they would rejoice, but not simply because the cause of their grief (Jesus’ death) had been undone, but also because they would then see it with new eyes, with new understanding.
It is not obvious in the NIV translation, but verse 23 uses two different words for “ask” which have slightly different shades of meaning: asking about something and asking for something. In v.23a the sense is that they won’t be asking any more questions (as they were in vv.17,18), because then they will understand – understand the reason for Jesus’ death and all that it accomplished: preparing a home for us in heaven for eternity (14:2,3) and preparing a home for God in our hearts now (14:23).
These verses all speak of our relationship with the Father – knowing the Father (v.25) and being sure of His love (v.27) – a relationship expressed in confident prayer. That we ask in Jesus’ name is not to imply that our access to the Father is indirect, as though we ask Jesus and he asks God, as if God were just “a friend of a friend”. No Jesus says plainly (v.26b) “I am not saying I will ask the Father on your behalf” for the Father loves us. Our relationship with the Father is not second hand. And it is no longer distant, such that Jesus must speak in veiled terms (v.25), for we will know the Father. Jesus had said that he had revealed the Father to the disciples (14:9), but it is through the gift of the Spirit that we are helped to know Jesus and the Father properly (16:14,15).
Do unpack what it is to pray in Jesus name – a key phrase (vv.23,24,26). It means to come to the Father, not on our own merit, but on the basis of Christ’s merit: that should give us great cause to be bold and confident as we approach the Father. It must also mean praying in accordance with Jesus’ character and purpose, which of course qualifies the promise of v.23b, but not so as to empty it of its wonderful encouragement. And as we enjoy this relationship with the Father and come to Him in prayer, so we will know joy – complete joy. Perhaps for some of us, the reason for our joylessness is our prayerlessness.
The key word in this final bit of the chapter seems to be “believe” (which comes three times). What they are to understand and believe is stated in v.28: that Jesus is the eternal, incarnate Son of God, whose death is not the end of the road but his route to exaltation. The disciples think they’ve got it (v.29,30), but actually of course their faith is still pretty hazy and weak, and Jesus is probably being ironic in his reply – “You think you believe at last, do you? Sure you do. That’s why any moment you’re all going to scarper and abandon me”. But in him, as they believe and rest in him, they would know peace – even in the midst of trouble – because through his death Jesus has “overcome the world” (v.33). Believing who he is and trusting what he has done brings us peace, even when life is tough.