Jesus wants us to ask the Father. We should not be shy. In fact, boldness helps. If what we ask for is consistent with God’s principles for His World (Kingdom), asked in His name and His will, He will give it to us. We must ask in faith. We must believe God will act.
God delights in giving me what He has in heaven. It tickles Him pink!!!
Wow, what joy that is when it happens.
So also, you have sorrow now, but I will see you again, and your hearts will rejoice, and no one will take your joy from you. In that day you will ask nothing of me. Truly, truly, I say to you, whatever you ask of the Father in my name, he will give it to you. Until now you have asked nothing in my name. Ask, and you will receive, that your joy may be full. 
It is important to note that the text uses two different words for “ask,” although they can be used interchangeably.
- The word used in John 16:19, 23a, and 26 means “to ask a question” or “to ask a request.” It is used when someone makes a request of someone equal.
- The word translated “ask” in John 16:23b, 24, and 26b (“pray”) means “to request something of a superior.”
- This latter word was never used by Jesus in His prayer life because He is equal to the Father.
- We come as inferiors to God, asking for His blessing; but He came as the very Son of God, equal with the Father.
What period of time did Jesus mean by “in that day”? I think He was referring to the time after the coming of the Spirit. He promised them in John 16:22 that He would see them again, and He kept His promise. He spent forty days with them after His resurrection, teaching them clearly the truths they needed to know in order to take His place and minister on earth. “That day” cannot refer to the day of His return for His church, because there is no evidence in Scripture that we shall pray to Him after we get to heaven.
Jesus knew that they wanted to ask Him a question. He assured them that a day would soon come when they would not ask Him questions. Instead, they would pray to the Father and He would meet their needs.
- This was the promise that they desperately needed to believe: that the Father loved them and would hear their requests and meet their needs.
- While Jesus was on earth, He met all the needs of His disciples.
- Now He would return to the Father, but the Father would meet their needs.
- Here is the wonderful promise and privilege of prayer.
Our Master and the Messiah Jesus had mentioned prayer many times in His ministry, and He had set the example for prayer in His own life. He was indeed a man of prayer. In His Upper Room message, Jesus emphasized prayer. He made it clear that believing prayer is one of the secrets of a fruitful discipleship life.
James, the brother of Jesus got it.
If any of you lacks wisdom, let him ask God, who gives generously to all without reproach, and it will be given him. But let him ask in faith, with no doubting, for the one who doubts is like a wave of the sea that is driven and tossed by the wind. For that person must not suppose that he will receive anything from the Master [Lord]; he is a double-minded man, unstable in all his ways. 
God’s Goal: The key is to ask in faith. We cannot doubt. Not at all. If we doubt, we can be sure we will receive nothing. Not. A. Thing.
 The Holy Bible: English Standard Version. (2016). (Jn 16:22–24). Wheaton, IL: Crossway Bibles.
 Wiersbe, W. W. (1996). The Bible exposition commentary (Vol. 1, p. 365). Wheaton, IL: Victor Books.
 The Holy Bible: English Standard Version. (2016). (Jas 1:5–8). Wheaton, IL: Crossway Bibles.