David in Bristol, Connecticut writes in and asks this, "Pastor John, over the last year, the Lord has taught me much about prayer, both by study of His Word and by lots of doing and failing at it. While I'm sure there will always be some mystery to prayer, the one thing that I've always struggled with is how to know if and when to stop praying for something, especially related to 1 John 5:14-17, since God's timing is rarely, if ever, ours, how do we know when to persevere in asking Him for something and when to stop, because nothing is changing and it seems to be God saying no?" Well, this is one of these questions where I'm going to see how much I can say when I don't know the answer.

And I hope it's not fog, and I'm saying it up front so everybody will know it's not, I'm not trying to hide it. I don't know for sure, but this may help. It helps me to think out loud like this. Isn't it significant? I think it is. That in the Bible, we have a statement, "You have not because you asked not," James 4:2.

But we don't have a statement, "You prayed too much or too long." We don't have a statement that says, "You have things I did not want to give you because you kept on asking me when it was time to quit." We don't have anything like that. In fact, all the emphasis in the New Testament is in the other direction.

Keep on praying. Don't lose heart. Ask, seek, knock. Wake up your friend at midnight if you must. Go back to the city judge over and over until he gives you justice, even though he just wants you off his back. I mean, those are amazing, horrible pictures of God. And the point is, he loves when we keep on coming and badgering him for something we want very badly according to his revealed will.

But here we have this difficult verse that was referred to in the question, John 5, 16. "If anyone sees his brother committing a sin not leading to death, he shall ask, and God will forgive him to those who commit sins that do not lead to death." There is sin that leads to death.

I do not say one should pray for that. All wrongdoing is sin, but there is sin that does not lead to death. That's 1 John 5, 16 and 17. Now notice, it does not say, "Don't pray about sin that leads to death." It says simply, "There is sin that leads to death.

I don't say that one should pray for that." It does amount, doesn't it, to a permission at least not to pray about sin that leads to death. And that's what makes the question so hard, like David says. How do we know? How do we know when a person has sinned unto death?

That is, there's not going to be any forgiveness. He's hardened himself so many times and so long, God has withdrawn from him, and there's not going to be any repentance on his part, and therefore not going to be any forgiveness on God's part. How do we know when that's happened?

It's not a particular sin. Get that out of the courtroom right away. It's not murder or rape or treason, because it doesn't say "the sin," like the unforgivable sin. That's not what this is about. It's not "the sin" or "a sin" that leads to death. It is sin or sinning unto death.

It's not the act. It's the depth and irreversibility of the act that a person has sinned so long they're not able to repent anymore. But how do we know that? And the answer is, "I don't know." But it might help to point to an analogy with a similar kind of difficulty.

Jesus said in Matthew 7, "Do not give dogs what is holy, and do not throw your pearls before pigs, lest they trample them under foot and turn to attack you." So there seems to be a kind of hardness and resistance and cynical attitude that you should not share the most precious truths with.

People are so utterly hard and cynical that they'll only trample your gospel words under their feet. How do we know when that is? I mean, Paul spoke to people who then threw him in prison and chanted songs for two hours to false gods. I mean, that's a lot of trampling going on in response to Paul's preaching.

And Jesus spoke, and people killed him. That's trampling the pearl of great price. So, in the one case, we don't have to pray for certain hardened sinners. In the other case, we shouldn't give holy things to the certain hardened sinners. And when does that apply? I don't know. But it may be that just knowing that such situations exist will help us, by the Holy Spirit, discern when we are in one.

And I'll just say, last thing, Tony, that this hit home to me for my grandmother. She's gone now, and in heaven, I frankly doubt. But she's the closest one I came to where I almost said to the Lord, "I'm not going to pray for her anymore." She is so cynical to everything I say.

She turns everything on its head. She's a terrible model for my grandkids, her grandkids, and actually her great-grandkids. I say grandmother, great-grandmother. My parents were not like that. She was my grandmother, and so she was a bad example. But frankly, I couldn't stop. I couldn't bring myself to stop praying for her conversion.

I've never, frankly, come to a situation where I've said, "That person is beyond my prayers." Excellent. That's very helpful, Pastor John. Thank you. And on this topic of prayer, be sure to check out episode #123 in this podcast, which is titled "How Food and Sex Are Made Holy," and also episode #124 titled "Mealtime Prayers--Necessary or Optional?" We will return on Monday with a new episode.

Until then, be sure to check out the Ask Pastor John app for the iPhone and the Android, and check out our website, DesiringGod.org, where you can find an archive of thousands of books, articles, sermons, and other resources, all free of charge from John Piper, and all intended to help explain why God is most glorified in us when we are most satisfied in Him.

I'm your host, Tony Reinke. Have a great weekend.