The most afraid I’ve ever been was the time I got lost in the woods after dark. My brother and I were out with some youth group friends playing a game of paintball in the pine forest of East Texas. As a moonless night fell, my heart rate rose. Being surrounded by the blinding dark and knowing that there were unseen others in the dark hunting us was a hair-raising experience.
Darkness is often used in the Bible to describe a range of different things. In this chapter, we are going to look at two different uses of the concept of darkness. The first use, as we will see, represents eternal condemnation in Hell. Let’s take a look at Jude 1:12-13.

…they feast with you without fear, serving only themselves. They are… wandering stars for whom is reserved the blackness of darkness forever.⁠1

These verses are discussing the actions and final destiny of a group of unsaved persons. Here it says that the “blackest of darkness” is reserved for them, and that this blackest of darkness will be an eternal experience. In case we have any doubt that he is talking about the destination of the unsaved in Hell, he clarifies toward the beginning of the chapter.

…the Lord, having saved the people out of the land of Egypt, afterward destroyed those who did not believe. And the angels who did not keep their proper domain, but left their own abode, He has reserved in everlasting chains under darkness for the judgment of the great day;⁠2

This illusion to everlasting chains and once again darkness is referenced for both, unbelievers and fallen angels. Clearly, Jude is using the concept of darkness to illustrate Hell. It’s by the grace of God that those who believe in his Son, will never have to experience this blackest darkness. Therefore, the black darkness described by Jude, and avoiding it, is a matter of salvation.
However, it’s important to know that the Bible doesn’t always use darkness as a metaphor for Hell and a call for salvation. In fact, the Gospel of Matthew has a handful of references to darkness, but he is not speaking of Hell.
In this encounter, a non-Jewish military man comes to Jesus to ask that his servant be healed. The Roman Centurion demonstrates great faith, even though he is not of the Jewish religion. Jesus is impressed and delivers these amazing words.

“Assuredly, I say to you, I have not found such great faith, not even in Israel! And I say to you that many will come from east and west, and sit down with Abraham, Isaac, and Jacob in the kingdom of heaven. But the sons of the kingdom will be cast out into outer darkness. There will be weeping and gnashing of teeth.”⁠3

Here, Jesus contrasts the faith of a gentile with the lack of faithfulness of some Jews. He teaches that gentiles, those from east and west, will sit down with Abraham, Isaac, and Jacob. The image he gives here is one of a banquet or possibly some other honor ceremony in the Kingdom of Heaven. The most important humans who ever lived will be at this feast or ceremony. There will be gentiles there as well, given similar places of honor.
After explaining that, he teaches that the sons of the Kingdom will be cast out into outer darkness. Before we define the outer darkness, let’s find out what it means to be sons of the kingdom. The title is used by Jesus a few chapters later and he defines the term very clearly. He gives a parable in which he explains that believers will be separated from unbelievers. He uses an agricultural analogy to explain that the good seeds are saved people and weeds (called tares) are not.

…the good seeds are the sons of the kingdom.⁠4

Here we find that the sons of the kingdom are saved. The parable of the wheat and the weeds doesn’t indicate how faithful these sons of the kingdom are, only that they have everlasting life.
So, what then does he mean when he says,

But the sons of the kingdom will be cast out into outer darkness. There will be weeping and gnashing of teeth.”⁠5

Obviously many have assumed that, being cast into outer darkness is a description of being cast into Hell, but that doesn’t work with the context.
First notice where this event is taking place.

“…many will come from east and west, and sit down with Abraham, Isaac, and Jacob in the kingdom of heaven.”⁠6

This feast is taking place in the kingdom of heaven. It then says that,

“…But the sons of the kingdom will be cast out…”⁠7

If I threw you out of my house, doesn’t that mean you would have been inside my house first? If they are to be cast out of something, they must first be inside that same something. So what are they inside of before they can be cast out? Well, for one they are inside the kingdom of heaven since that is where the feast is taking place. There is no other way to read it. By that we know that they must be saved because Jesus said that no one will see or enter the kingdom of God unless they are born-again.⁠8
Now here’s a twist that you may not have noticed. It doesn’t actually say they are cast out of the kingdom of heaven. The grammar indicates that they are cast out of the feast or ceremony. See how Jesus says,

“…But the sons of the kingdom will be cast out into…”⁠9

He says they are being cast out of one area but into another. What is it that they are being cast into? It’s called outer darkness. It does not say they are cast out of the kingdom. Instead we see that they are cast into what is defined as, “outer.” It’s outer, not out. If I visited the outer edge of the United States, would I still be in the country? Yep. For something to be the outer part, it must still be inside the whole. So, these sons of the kingdom, who are saved, are tossed out of the feast or ceremony but are still inside the kingdom of heaven. We will get more clarity on what the outer darkness is with the next parable that we look at.

“For the kingdom of heaven is like a man traveling to a far country, who called his own servants and delivered his goods to them. And to one he gave five talents, to another two, and to another one, to each according to his own ability; and immediately he went on a journey. Then he who had received the five talents went and traded with them, and made another five talents. And likewise he who had received two gained two more also. But he who had received one went and dug in the ground, and hid his lord’s money. After a long time the lord of those servants came and settled accounts with them.
“So he who had received five talents came and brought five other talents, saying, ‘Lord, you delivered to me five talents; look, I have gained five more talents besides them.’ His lord said to him, ‘Well done, good and faithful servant; you were faithful over a few things, I will make you ruler over many things. Enter into the joy of your lord.’ He also who had received two talents came and said, ‘Lord, you delivered to me two talents; look, I have gained two more talents besides them.’ His lord said to him, ‘Well done, good and faithful servant; you have been faithful over a few things, I will make you ruler over many things. Enter into the joy of your lord.’
“Then he who had received the one talent came and said, ‘Lord, I knew you to be a hard man, reaping where you have not sown, and gathering where you have not scattered seed. And I was afraid, and went and hid your talent in the ground. Look, there you have what is yours.’
“But his lord answered and said to him, ‘You wicked and lazy servant, you knew that I reap where I have not sown, and gather where I have not scattered seed. So you ought to have deposited my money with the bankers, and at my coming I would have received back my own with interest. So take the talent from him, and give it to him who has ten talents.
‘For to everyone who has, more will be given, and he will have abundance; but from him who does not have, even what he has will be taken away. And cast the unprofitable servant into the outer darkness. There will be weeping and gnashing of teeth.’⁠10

This story focuses on three servants. The servants represent three saved people. Notice that even at the close of the story, the least faithful one is still called “servant” albeit lazy and unprofitable servant. Although they are rewarded differently for their service, non of them ever stops being a servant of their Lord. Even the last reference to the unfaithful one reiterates the master-servant relationship, even though the master is disciplining him.
His master is so upset with him, he ejects him from his house and into the dark. Some have claimed that this could rightly be translated as the darkness outside. The unprofitability of the servant has so enraged his master that he is made to go and sleep outside. His place of comfort and inside the house is revoked because he’s been so unfaithful. He’s made to go out and reside where the animals have to sleep. His status is no higher than the beasts who live in the fields around the house. Once the unprofitable servant is out there he cries in the darkness. He’s full of remorse for his bad behavior. The stories tell us that weeping and gnashing of teeth accompany being shut out into the darkness.
Those that claim the darkness outside is an analogy for Hell might say that only the unsaved will weep and gnash their teeth. However, Jesus wept⁠11, and God gnashed his teeth⁠12, so weeping and gnashing of teeth are not things reserved only for unbelievers, or unsaved. Weeping and gnashing of teeth is an expression of regret and remorse, sometimes even frustration. Why will there be weeping and gnashing of teeth? 1 Corinthians 3:15 tells us that there will be believers who will suffer loss while they are in heaven. The loss they suffer will be missing out on rewards, and fellowship with Christ because of their lack of diligence during their mortal lives. They will experience regret and frustration at themselves but they will be saved.⁠13
What’s more, we know that there will be weeping in the Kingdom of Heaven because it is not until the New Heaven and the New Earth that God will wipe away every tear from their eyes.⁠14 That far-future event is the point at which crying will be done away with. For him to wipe away tears then, there must be crying that exists up until that time in order that it may be wiped away. So, while the Kingdom of God will be a very joy-filled place for its citizens, there will still be those who experience regret and even cry in the millennial kingdom of heaven. Weeping in the Kingdom of Heaven will be centered around regret for a lack of faithfulness to Christ while in their mortal bodies. Those who believed in Jesus and were saved but did not choose a life of discipleship will regret it tremendously when Christ comes in his kingdom. They will be barred from the fullest experience in the Kingdom of Heaven.
There is one more reference to the outer darkness, also found in Matthew.

“The kingdom of heaven is like a certain king who arranged a marriage for his son, and sent out his servants to call those who were invited to the wedding; and they were not willing to come. Again, he sent out other servants, saying, ‘Tell those who are invited, “See, I have prepared my dinner; my oxen and fatted cattle are killed, and all things are ready. Come to the wedding.” ’ But they made light of it and went their ways, one to his own farm, another to his business. And the rest seized his servants, treated them spitefully, and killed them. But when the king heard about it, he was furious. And he sent out his armies, destroyed those murderers, and burned up their city. Then he said to his servants, ‘The wedding is ready, but those who were invited were not worthy. Therefore go into the highways, and as many as you find, invite to the wedding.’ So those servants went out into the highways and gathered together all whom they found, both bad and good. And the wedding hall was filled with guests. “But when the king came in to see the guests, he saw a man there who did not have on a wedding garment. So he said to him, ‘Friend, how did you come in here without a wedding garment?’ And he was speechless. Then the king said to the servants, ‘Bind him hand and foot, take him away, and cast him into outer darkness; there will be weeping and gnashing of teeth.’⁠15

What was the harshest punishment that appeared in this above story? The harsher punishment is the point at which the king, “sent out his armies, destroyed those murderers, and burned up their city.” What is the harshest punishment that God will enact against evil unbelievers? Hell is waiting for those who do not believe in Jesus, and is the primary and most severe of the punishments that God will dispense.
There seems to be a dual nature of the king’s punishment. While it likely represents God’s temporal judgments on the nation of Israel, in which armies came against them and burned their cities. It too must represent not only the physical fate of those who refused to believe for salvation, but their eternal fate as well. It must represent both temporal wrath and eternal Hell. If destroying the murderers and burning their city is a reference to Hell, then what does it mean that the poorly dressed man is cast into outer darkness? It must mean something else; something much less severe.
Notice that the man who does not have a wedding garment is not killed. His city is not burned. The army is not employed to hunt him down. In fact, the King calls him “friend,” when he first addresses him. The man is speechless. He would have known that there is a dress code for a royal banquet, and therefore should have been preparing for the feast. Because he doesn’t meet the royal expectation, he is tied up and tossed out of the wedding feast.
There are those that will still try to claim that outer darkness must mean Hell, but even they would have to admit that this man is treated with a much less severe punishment than that which the murderers received. Therefore, outer darkness must be something less severe than being condemned to Hell. In fact, as we’ve seen in the previous two examples, it is. Notice that the feast is likely happening at night, since it took all day to get anyone to attend. So the man who was tied and removed from the banquet is being tossed outside in the dark. The king doesn’t revoke his citizenship, kick him out of the Kingdom, or kill him. Instead, he simply removes him from his feast.
Outer darkness suggests a sense in which the one thrown out has to stand outside in the dark. All the while, he knows an incredible banquet is taking place inside. He had the ability to prepare but he chose not to. That this disappointing turn of events produces tears is no surprise.
What we’ve discovered in this chapter is that Jude spoke of the blackest darkness as an image of Hell. That however, is not the same thing as being thrown into the outer darkness. Jesus spoke of the outer darkness as a dishonored experience in Heaven. This is certainly a reference to a call to discipleship. Therefore, avoiding the blackest darkness is possibly only by salvation, whereas avoiding the outer darkness is possibly by discipleship.

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1 Jude 12–13.
2 Jude 5–6.
3 Matthew 8:10–12.
4 Matthew 13:37–38.
5 Matthew 8:10–12.
6 Matthew 8:10–12.
7 Matthew 8:10–12.
8 John 3:3,5
9 Matthew 8:10–12.
10 Matthew 25:14–30.
11 John 11:13
12 Job 16:9
13 1 Corinthians 3:15
14 Revelation 21:4
15 Matthew 22:2–14.