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At the first reading of Joh_16:23 there seems to be a contradiction in the words.
Christ tells them in the former part of the verse, that they shall ask him nothing in that day; and yet promises that whatever they ask shall be given them, in the latter part of the verse.
To resolve this, know that there is a two-fold asking, one by way of question, the other by way of petition.
The former is asking that we may know, or be informed in, what we doubt; the latter is asking that we may receive, and be supplied with what we want.
Now when Christ saith, In that day ye shall ask me nothing; it is as much as if he had said, "At present you understand but little of the mysteries of religion, and therefore ye put questions about many things: but, in that day, when the Comforter comes, ye shall be so clearly enlightened by him, that ye shall not need to ask me any more questions." But when Christ saith, Whatever ye ask of the Father in my name, he will give it; the meaning is, "In that day when I have left the world, and ascended to my Father, you shall not need to address your prayers to me, but to my Father in my name."
But what is it to pray in the name of Christ?
Answer, it is more than to name Christ in prayer: it is easy to name Christ in prayer, buy no easy thing to pray in the name of Christ.
To pray in the name of Christ, is,
1. To look up to Christ, as having purchased for us this privilege, that we may pray: for it is by the blood of Christ that we draw near to God, and that a throne of grace is open to us.
2. To pray in the name of Christ, is to pray in the strength of Christ, by the assistance of his grace, and the help of his Holy Spirit.
3. To pray in the name of Christ is to pray by faith in the virtue of Christ's mediation and intercession, believing that what we ask on earth, he intercedes for and obtains in heaven. To pray thus is no easy matter: and unless we do pray thus, we do not pray at all.
Hitherto have ye asked nothing in my name Joh_16:24; that is, explicitly and expressly in my name, or by me, as mediator betwixt God and man, and with respect to my merits. Do this after my death, resurrection, and intercession at the right hand of God, and you shall receive such answers as will fill you with joy; for the saints of God under the Old Testament, and the apostles themselves under the New, and hitherto put up all their petitions in the name of the Messiah, though not in the name of Jesus.
But now he exhorts them to eye his mediatory office in all their addresses to God, and promises them whatsoever he had purchased of the Father by his sufferings and satisfaction, they should obtain it for the sake of his prevailing intercession.
Learn hence, that it is a mighty encouragement to prayer, that now, under the gospel, the person of the Mediator is exhibited in our flesh, has satisfied divine Justice in our nature, and in that nature intercedes as mediator, for whatever he purchased as our surety.
Hence is the encouragemnt; Whatsoever ye ask the Father in my name, he will give it you.