KJV 1 Cor 14:15 What is it then? I will pray with the spirit, and I will pray with the understanding also: I will sing with the spirit, and I will sing with the understanding also.Nearly always the meaning is that our singing/praying is to be done with a heartfelt sincerity, and with full understanding of what we're singing/praying about.
But this just highlights how easy it is to take Scripture out of context. If we read the verse above out of context, it sounds exactly how it is often used - that we're to be fully aware of what we're singing/praying at all times, and we're to be sincere about it.
But in context, that's not what the phrase says at all.
Throughout this entire chapter, Paul is contrasting the value of heart-felt sincerity in worship versus educational, church-strengthening information.
He's not saying we should do both at the same time; he's saying there's a time and a place for "brain-dead", "spirit-based" worship, and there's a time and a place for "brain fully-engaged" thinking. And he will do both. Not at the same time, but when each is appropriate.
His emphasis throughout the entire chapter is that in the assembly (i.e., when we "do church" with others), the spiritual worship is inappropriate, and only the understandable worship is appropriate.
Notice how he makes the contrast starting in the very beginning of the chapter, starting at verse 1 (I'm going to switch away from the KJV to a more understandable version, the Holman Christian Standard Bible):
Pursue love and desire spiritual gifts, and above all that you may prophesy. For the person who speaks in another language is not speaking to men but to God, since no one understands him; however, he speaks mysteries in the Spirit. But the person who prophesies speaks to people for edification, encouragement, and consolation. The person who speaks in another language builds himself up, but he who prophesies builds up the church. I wish all of you spoke in other languages, but even more that you prophesied. The person who prophesies is greater than the person who speaks in languages, unless he interprets so that the church may be built up.Notice that speaking in another language is not speaking to men, but to God, and is mysterious.
He continues with this thought, but I'll skip a fair portion of it and jump to verse 13:
Therefore the person who speaks in another language should pray that he can interpret. For if I pray in another language, my spirit prays, but my understanding is unfruitful. What then? I will pray with the spirit, and I will also pray with my understanding. I will sing with the spirit, and I will also sing with my understanding. Otherwise, if you praise with the spirit, how will the uninformed person say “Amen” at your giving of thanks, since he does not know what you are saying? For you may very well be giving thanks, but the other person is not being built up. I thank God that I speak in other languages more than all of you; yet in the church I would rather speak five words with my understanding, in order to teach others also, than 10,000 words in another language.Notice the context. He's talking about speaking in another language, which no man understands; even the speaker himself has unfruitful understanding. He says such prayer is perfectly acceptable worship ("you may very well be giving thanks"), but that it's of no value in the assembly. Such prayer builds up the one doing the praying (v. 4), but it doesn't build up the assembly, and everything in the assembly is to be geared toward "edification" (building up of the "edifice"), as he explicitly says in verse 26:
Whenever you come together ... [a]ll things must be done for edification.Paul is not saying that when he sings/prays, he'll do so with both spirit and understanding at the same time; he's saying that sometimes he'll sing/pray with the Spirit, when he has no understanding of what he's saying (brain-dead glossalolia, (either human or angelic language-speaking (1 Cor 13:1)), or perhaps moaning, chanting, etc, but in any case, nothing understandable), and in some cases he'll sing/pray with his brain engaged, with understanding. Singing/praying with the spirit is mutually exclusive to singing/praying with the understanding. Biblically, it's impossible to do both at the same time.
When we try to use this passage to teach that we are to sing/pray with the spirit at the same time that we sing/pray with the understanding, we have changed the meaning of "with the Spirit" to something other than what the Scriptures actually say. We have become unscriptural.
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