Jesus makes the application of the simile from the preceding verse. Notice that Jesus says that “now” is their time of grief. He knows that their pain is already present.

In (16:19) He had said that they would see Him, but now He says that He will see them. Westcott observes that this shows “that we are the objects of God’s regard.” Our loving, compassionate Lord always has us in His sight. Why? Because He takes great delight in us (Zeph 3:17). He looks for us and is looking for opportunities to bless us. Even though He had abandoned them for a while, He would return to them (Isa 54:7).

John 16:19  Jesus saw that they wanted to ask him about this, so he said to them, “Are you asking 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’?

Zephaniah 3:17  The LORD your God is with you, he is mighty to save. He will take great delight in you, he will quiet you with his love, he will rejoice over you with singing.”

Isaiah 54:7  “For a brief moment I abandoned you, but with deep compassion I will bring you back.

The disciples will rejoice and that rejoicing will be a permanent thing (Luke 24:52,53). This does not mean that they will never experience sorrow again, but that the joy they will receive will be deep and independent of the world and the circumstances of their lives. McGarvey says it this way: “The joyful hopes which come to us through the resurrection of Jesus are beyond the reach of the despoiling hand of man.” Again, this is a promise to us, too (Ps 30:5,11). Note that the same thing happened to Jesus (Heb 12:2).

Luke 24:52-53  Then they worshipped him and returned to Jerusalem with great joy.  And they stayed continually at the temple, praising God.

Psalms 30:5  For his anger lasts only a moment, but his favour lasts a lifetime; weeping may remain for a night, but rejoicing comes in the morning.

Psalms 30:11  You turned my wailing into dancing; you removed my sackcloth and clothed me with joy,

Hebrews 12:2  Let us fix our eyes on Jesus, the author and perfecter of our faith, who for the joy set before him endured the cross, scorning its shame, and sat down at the right hand of the throne of God.

Much of our joy in this life depends upon the people around us and the circumstances we find ourselves in, but for the Christian, it doesn’t stop there. Our joy comes from a deep well that will never run dry and which no enemy can ever approach. That well runs deep into the bedrock of an eternal, unchangeable God Who loves us, wants the best for us, and has proven it by sending his very own Son to die for us. Neither people nor circumstances have any power to separate us from that joy (Rom 8:35-39), but they can tempt us to try to keep us from drinking of it. The answer is, again, to love Jesus with all of our hearts, fix our eyes upon Him, and receive all He has for us in faith, dwelling not upon the sorrow, but anticipating the joy.

Tis good for thee to walk by faith and not by sight;
Take it on trust a little while;
Soon shalt thou read the mystery right,
In the full sunshine of His smile.

John Keble

Romans 8:35-39  Who shall separate us from the love of Christ? Shall trouble or hardship or persecution or famine or nakedness or danger or sword?  As it is written: “For your sake we face death all day long; we are considered as sheep to be slaughtered.”  No, in all these things we are more than conquerors through him who loved us.  For I am convinced that neither death nor life, neither angels nor demons, neither the present nor the future, nor any powers,  neither height nor depth, nor anything else in all creation, will be able to separate us from the love of God that is in Christ Jesus our Lord.