Since the Lord had been talking about the coming of the Comforter (16:7-14), the “day” of which He speaks (v.23) is “the Day of Pentecost” (Acts 2:1). That’s when they wouldn’t need to ask the Lord any questions, as they had been wanting to do (16:19). They wanted to ask questions because they didn’t understand what He had said, but at Pentecost the Spirit taught them all things (John 14:26; IJo.2:20) and they needed to ask Him “nothing” (John 16:23). I’d find that comforting, how about you?
Since the Spirit also controlled them (Ezek. 36:27) the Lord could promise the apostles all they asked for in prayer if they asked in His name (John 16:23) something they’d nev-er done before (v.24). We too pray in His name (Eph.5:20) but before Pentecost men prayed in Abraham’s name (Gen.32:9; IKi.18:36) because God made promises to him and his seed, so his seed prayed in his name to remind You.
The Lord had promised “ask, and ye shall receive” (Jo.16: 24) before (Mt.7:7-11), but only concerning “good things” connected with the Spirit (Lu.11:13). Good things like the “daily bread” (11:1-9) they’d need when the beast issues his mark and they can’t buy bread. God met their need of bread thru the saints at Pentecost and will meet it with manna in the Tribulation. They could also ask for “good things” like grace and glory (Ps.84:11) and truth and right-eousness (85:11,12), which they’ll get in the kingdom, along with a fruitful “land.” Since our land is not the land He meant, we can’t claim that promise, nor the the “good thing” of dwelling “safely” in the kingdom (Jer.33:14-16). They could also ask for and receive “wisdom” (James 1:5)
They were never promised to be given anything they asked for, which is never good for men (Ps.106:15) and won’t be until men are filled with the Spirit as they were at Pente-cost. Since we don’t know what to pray for (Ro.8:26) the worse judgment God could give us is to give us anything we ask for (cf. Pr.1:30,31). The world thinks that things like houses, cars and possessions bring joy, so that’s what they pray for, but the Lord said that these “good things” of the kingdom will bring joy (Jo.16:24), so that’s what Paul prayed for us. Things like wisdom & the knowledge of the truth (Eph.1:15-17) & righteousness (IICo.13:7; Ph.1:9-11).
A “proverb” (John 16:25) is “a short sentence often re-peated, as in Proverbs 4:5,7;16:16. But that can’t be what the Lord meant here, for He said the day would come when He would speak “plainly” and not in proverbs. What’s un-plain about a short sentence often repeated? Well, the Greek and English word “proverb” can mean parable, and the words are used interchangeably in Habakkuk 2:6. Numbers 23:7 is more of a proverb than a parable. Unplain speech is parabolic, whereas plain speech is not (John 11: 11-14). “A little while and ye shall not see Me” (16:16) is parabolic, so He had been speaking in proverbs and para-bles (16:21,22), but that would end at Pentecost when He would “shew” (i.e., tell, cf. ICor.15:51) the apostles things plainly through the Spirit, who taught them all things.
The Lord said He wouldn’t pray for things for them (John 16:26)—not because He didn’t want to, but rather because He didn’t have to. They didn’t need Him to since the Father loved them because they believed in Him (v.27). God loves all men (John 3:16) but believers are His “beloved”, whom He loves more (cf. Deut.21:15 cf. Gen. 29:30,31).
The apostles interrupted Him (v.28) to say He was speaking plainly (v.29) because now they were “sure” He was the Christ (v.30), and because He knew what they were think-ing (16:19 cf. I Ki.8:9). The Lord knew their hearts though (Jo.16:31) and knew they were about to forsake Him, and that would leave Him alone (v.32). But the Father was with Him (cf. Gen.22:8), the Father who justified Him (Isa. 50:6-9), just as He is with us justified ones (Ro.8:33,34).
The apostles were heading into the great tribulation (John 16:33), but the Lord promised to be their peace (v.33 cf. Micah 5:5). If they could have peace in the worst tribulation the world has ever known, surely you can have peace in yours—if you have Him. If you have Him, you can be more than just comforted in your tribulation, you can cheerful, you can “be of good cheer” (John 16:33).