When is "that day"? When the Ascended Lord makes you one with the Father. In that day you will be one with the Father as Jesus is, and "in that day," Jesus says, "ye shall ask Me nothing." Until the resurrection life of Jesus is manifested in you, you want to ask this and that; then after a while you find all questions gone, you do not seem to have any left to ask. You have come to the place of entire reliance on the resurrection life of Jesus which brings you into perfect contact with the purpose of God. Are you living that life now? If not, why shouldn’t you?
There may be any number of things dark to your understanding, but they do not come in between your heart and God. "And in that day ye shall ask Me no question" – you do not need to, you are so certain that God will bring things out in accordance with His will. John 14:1 has become the real state of your heart, and there are no more questions to be asked. If anything is a mystery to you and it is coming in between you and God, never look for the explanation in your intellect, look for it in your disposition, it is that which is wrong. When once your disposition is willing to submit to the life of Jesus, the understanding will be perfectly clear, and you will get to the place where there is no distance between the Father and His child because the Lord has made you one, and "in that day ye shall ask Me no question."
Bible in One Year: 2 Chronicles 4-6; John 10:24-42