John 16:23-25

23 "And in that day you will ask Me nothing. Most assuredly, I say to you, whatever you ask the Father in My name He will give you. 

24 Until now you have asked nothing in My name. Ask, and you will receive, that your joy may be full.

25 "These things I have spoken to you in figurative language; but the time is coming when I will no longer speak to you in figurative language, but I will tell you plainly about the Father.

The first part of verse 23 belongs at the end of verse 22. I will see you again (His second coming) and you will ask (question) Me nothing. They will know as they are known. There will be no more questions.

The second part of verse 23 goes with verse 24, beginning with "Most assuredly." When the Spirit comes, they were to ask in Christ's name (pray — a different word for "ask" than the earlier use in verse 23).

in that day (v. 23) — Christ's resurrection and following

ask (v. 23, first usage) = familiar entreaty, as a loved one

ask (v. 23, second usage) = petition, as a supplicant

whatever (v. 23) — in accordance with God's will, for the Son's glory and in our own best interest.

Verse 24 marks the end of the period when prayer should be said in the style of the Lord's prayer.

figurative language (v. 25) — proverbs. He knew they couldn't understand it all. When the Spirit came, He showed the Father plainly and they understood — especially about the Fatherhood of God and the sonship of the believer (Galatians 4:6; Romans 8:15-16).

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