We see the concept of “OUTER DARKNESS” mentioned three times in scripture:
1. The story of the Centurion
2. The Wedding Feast
3. Parable of the Talents

All three references are in the book of Matthew.
All three references also mention ‘weeping and gnashing of teeth.’
All three references are direct quotes of Yeshua Messiah.

If our Messiah spoke of it, then it must be true, and we should know and understand these warnings.

Jesus Heals a Centurion’s Servant

⁵ Now when Jesus had entered Capernaum, a centurion came to Him, pleading with Him, ⁶ saying, “Lord, my servant is lying at home paralyzed, dreadfully tormented.”
⁷ And Jesus said to him, “I will come and heal him.”
⁸ The centurion answered and said, “Lord, I am not worthy that You should come under my roof. But only speak a word, and my servant will be healed. ⁹ For I also am a man under authority, having soldiers under me. And I say to this one, ‘Go,’ and he goes; and to another, ‘Come,’ and he comes; and to my servant, ‘Do this,’ and he does it.”
¹⁰ When Jesus heard it, He marveled, and said to those who followed, “Assuredly, I say to you, I have not found such great faith, not even in Israel! ¹¹ 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.¹² But the sons of the kingdom will be cast out into outer darkness. There will be weeping and gnashing of teeth.” ¹³ Then Jesus said to the centurion, “Go your way; and as you have believed, so let it be done for you.” And his servant was healed that same hour.  [Matthew 8:5-13]

This first story speaks of the great faith of the Centurion.
His faith is contrasted to the lack of faith that Yeshua observed in Israel.  Not good, right?
Messiah says those of Israel who are without the faith of the centurion, the sons of the kingdom, will be cast into outer darkness!!
Whoa, that’s a serious warning, going out to people who probably think and believe they are “in the kingdom.”
Well, even Yeshua says they are sons of the kingdom.
Is it possible to be “in the kingdom” and still be cast out into a horrible place?
This immediately reminds me of Matthew 5:17-19
¹⁷ “Do not think that I came to abolish the Torah or the Prophets! I did not come to abolish, but to fulfill. ¹⁸ Amen, I tell you, until heaven and earth pass away, not the smallest letter or serif shall ever pass away from the Torah until all things come to pass. ¹⁹ Therefore, whoever breaks one of the least of these commandments, and teaches others the same, shall be called least in the kingdom of heaven. But whoever keeps and teaches them, this one shall be called great in the kingdom of heaven.

I know of people who said they are aiming to be “least in the kingdom”.
Is that a good thing or a bad thing?
Is that the heart we want to show our Messiah?
Do we want to admit to Him that we are only willing to do as little as possible, just as long as we can be least in the kingdom?
Is that going to make Him happy with us?

The Parable of the Wedding Feast

22 And Jesus answered and spoke to them again by parables and said: ² “The kingdom of heaven is like a certain king who arranged a marriage for his son, ³ and sent out his servants to call those who were invited to the wedding; and they were not willing to come. ⁴ 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.”’ ⁵ But they made light of it and went their ways, one to his own farm, another to his business. ⁶ And the rest seized his servants, treated them spitefully, and killed them. ⁷ But when the king heard about it, he was furious. And he sent out his armies, destroyed those murderers, and burned up their city. ⁸ Then he said to his servants, ‘The wedding is ready, but those who were invited were not worthy. ⁹ Therefore go into the highways, and as many as you find, invite to the wedding.’ ¹⁰ 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.
¹¹ “But when the king came in to see the guests, he saw a man there who did not have on a wedding garment. ¹² So he said to him, ‘Friend, how did you come in here without a wedding garment?’ And he was speechless. ¹³ 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.’
¹⁴ “For many are called, but few are chosen.”  [Matthew 22:1-14]

This parable is also fascinating.
Those who are called but not chosen will be tossed out of the wedding feast. Why? Because they are not dressed properly.

We see this in Revelation 3:4-5
 You have a few names even in Sardis who have not defiled their garments; and they shall walk with Me in white, for they are worthy. ⁵ He who overcomes shall be clothed in white garments, and I will not blot out his name from the Book of Life; but I will confess his name before My Father and before His angels.

This is encouraging, to those who have not defiled their garments. But what does that mean??

Revelation 22:14 tells us who will be included in the kingdom.
It is normally translated this way in English bible versions:
¹⁴ Blessed are those who do His commandments, that they may have the right to the tree of life, and may enter through the gates into the city.
However, translations that are more literal to the original text show this:
¹⁴ How fortunate are those who wash their robes, so that they may have the right to the Tree of Life and may enter through the gates into the city.

Keeping the commandments is considered to be the same as washing our robes, or having clean robes.
Going back to this parable, those who have defiled their spiritual garments by not keeping them clean [ie keeping the commandments of Yehova] will be thrown into outer darkness.
Did you understand this?
Not keeping the commandments/instructions of Yehova is how we defile our garments…
How do I know I’m right about this?
Hebrews 10:26-31 tells us there no longer remains a sacrifice for those who continue in willful sin…
Do you understand?
Messiah’s sacrifice, the one thing that allows us to have salvation through Him, no longer pertains to us if we continue in willful, on purpose sin.

[Matthew 25:14-30]
The Parable of the Talents
¹⁴ “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. ¹⁵ 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.¹⁶ Then he who had received the five talents went and traded with them, and made another five talents. ¹⁷ And likewise he who had received two gained two more also. ¹⁸ But he who had received one went and dug in the ground, and hid his lord’s money. ¹⁹ After a long time the lord of those servants came and settled accounts with them.
²⁰ “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.’ ²¹ 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.’²² 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.’ ²³ 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.’
²⁴ “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. ²⁵ And I was afraid, and went and hid your talent in the ground. Look, there you have what is yours.’
²⁶ “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. ²⁷ So you ought to have deposited my money with the bankers, and at my coming I would have received back my own with interest. ²⁸ Therefore take the talent from him, and give it to him who has ten talents.
²⁹ ‘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. ³⁰ And cast the unprofitable servant into the outer darkness. There will be weeping and gnashing of teeth.’  

Is this parable about gold?
Is this parable about money?
Is this parable about earning a profit?
No, no, and no…
This parable displays whether or not someone truly knows the God they serve, and whether or not they have a heart to serve Him.
The first two servants understood the character of Yehova.
They served Him well, because they understand the duty of man, given to us in Ecclesiastes 12 and in Revelation 14.

Ecclesiastes 12:13
¹³ Let us hear the conclusion of the whole matter:
Fear God and keep His commandments, For this is man’s all.
Revelation 14:12
Here is the patience of the saints; here are those who keep the commandments of God and the faith of Yeshua Messiah.

Those who TRULY KNOW the character of their God will do the things He says.  Their lives will show the fruit of their faith.
In this parable, the third servant did not know the true character of Yehova. This third servant was fearful and mistrusting of Yehova.
Instead of following His instructions, he buried his talent. He did not listen to, serve, and obey Yehova.

Is it enough to simply believe in Jesus?
Will that get us the promise of eternal life in heaven?
James 2:18-19
¹⁸ But someone will say, “You have faith, and I have works.” Show me your faith without your^[d] works, and I will show you my faith by my works. ¹⁹ You believe that there is one God. You do well. Even the demons believe—and tremble!

Even the demons believe, and shudder.
Nope, simple belief will not work for you, even though many churches teach this idea. This occurs because they take simple promises like John 3:16 and build doctrine from it, instead of building doctrine upon the whole of scripture.

Faith without works is dead.  Our works are the fruit in our lives, and it comes by listening to our Messiah, and doing the things He said.
He even admonishes some with this thought:
Luke 6:46
“But why do you call Me ‘Lord, Lord,’ and not do the things which I say? “

OK, so we’ve briefly discussed the three times outer darkness is mentioned in scripture.
But what IS outer darkness?
Sometimes I wish scripture would just tell us these things.
Is this something people used to know, so a full blown explanation was not required when these things were written?  Is this lost knowledge? Is it something we should know?
I’m not sure, but one thing is clear —  “there was weeping and gnashing of teeth.”

Outer darkness is not a good place to  be. I can say this as fact, with absolute certainty.
But now, we veer off into speculation.
Where is it?
What is it?
I don’t know, but here are some thoughts…

 Matthew 24:35
“Heaven and earth will pass away, but My words will by no means pass away.”

2Peter 3:10-14
¹⁰ But the day of the Lord will come as a thief in the night, in which the heavens will pass away with a great noise, and the elements will melt with fervent heat; both the earth and the works that are in it will be burned up. ¹¹ Therefore, since all these things will be dissolved, what manner of persons ought you to be in holy conduct and godliness, ¹² looking for and hastening the coming of the day of God, because of which the heavens will be dissolved, being on fire, and the elements will melt with fervent heat? ¹³ Nevertheless we, according to His promise, look for new heavens and a new earth in which righteousness dwells.

Messiah Himself tells us more than once in scripture that heaven and earth will pass away.
2Peter 3 tells us all will be burned up and destroyed. Verse 13 says we are to look towards a new heaven and a new earth.
Was Peter on drugs, or is this really going to happen?

Matthew 5:18
For assuredly, I say to you, till heaven and earth pass away, one jot or one tittle will by no means pass from the law till all is fulfilled. 
Mark 13:31
Heaven and earth will pass away, but My words will by no means pass away.
Luke 21:33
Heaven and earth will pass away, but My words will by no means pass away.
Isaiah 65:17
“For behold, I create new heavens and a new earth;
And the former shall not be remembered or come to mind.
Isaiah 66:22
“For as the new heavens and the new earth
Which I will make shall remain before Me,” says the Lord,
Revelation 21:1
Now I saw a new heaven and a new earth, for the first heaven and the first earth had passed away.

I think we have enough validation in scripture that the earth and the heavens are going to pass away, and that there will be new earth and heavens…  Can I explain all of this in intricate detail?
Nope.
But I can read it and believe it.

In John 14, Yeshua Messiah says that He goes to prepare a place for us, and that He will return:
John 14:2-3
In My Father’s house are many mansions; if it were not so, I would have told you. I go to prepare a place for you. ³ And if I go and prepare a place for you, I will come again and receive you to Myself; that where I am, there you may be also.

Let’s take a look at some of this restoration. Revelation 21 tells us about our eternal home, for those who are granted eternal life:

Revelation 21:9-27
The New Jerusalem
⁹ Then one of the seven angels who had the seven bowls filled with the seven last plagues came to me and talked with me, saying, “Come, I will show you the bride, the Lamb’s wife.” ¹⁰ And he carried me away in the Spirit to a great and high mountain, and showed me the great city, the holy Jerusalem, descending out of heaven from God, ¹¹ having the glory of God. Her light was like a most precious stone, like a jasper stone, clear as crystal. ¹² Also she had a great and high wall with twelve gates, and twelve angels at the gates, and names written on them, which are the names of the twelve tribes of the children of Israel: ¹³ three gates on the east, three gates on the north, three gates on the south, and three gates on the west.

¹⁴ Now the wall of the city had twelve foundations, and on them were the names of the twelve apostles of the Lamb. ¹⁵ And he who talked with me had a gold reed to measure the city, its gates, and its wall. ¹⁶ The city is laid out as a square; its length is as great as its breadth. And he measured the city with the reed: twelve thousand furlongs. Its length, breadth, and height are equal. ¹⁷ Then he measured its wall: one hundred and forty-four cubits, according to the measure of a man, that is, of an angel. ¹⁸ The construction of its wall was of jasper; and the city was pure gold, like clear glass. ¹⁹ The foundations of the wall of the city were adorned with all kinds of precious stones: the first foundation was jasper, the second sapphire, the third chalcedony, the fourth emerald, ²⁰ the fifth sardonyx, the sixth sardius, the seventh chrysolite, the eighth beryl, the ninth topaz, the tenth chrysoprase, the eleventh jacinth, and the twelfth amethyst. ²¹ The twelve gates were twelve pearls: each individual gate was of one pearl. And the street of the city was pure gold, like transparent glass.

The Glory of the New Jerusalem

²² But I saw no temple in it, for the Lord God Almighty and the Lamb are its temple. ²³ The city had no need of the sun or of the moon to shine in it, for the glory of God illuminated it. The Lamb is its light. ²⁴ And the nations of those who are saved shall walk in its light, and the kings of the earth bring their glory and honor into it. ²⁵ Its gates shall not be shut at all by day (there shall be no night there). ²⁶ And they shall bring the glory and the honor of the nations into it. ²⁷ But there shall by no means enter it anything that defiles, or causes an abomination or a lie, but only those who are written in the Lamb’s Book of Life.

We get a glimpse of the City of New Jerusalem.
It sounds like quite a fascinating place.
But here are a few things we learn:
1.  It has gates of entry, and each gate is ‘guarded’ by an angel.
2.  Why are angelic guards necessary?  Verse 27 tells us who is not allowed in…
3.  We also learn there is no sun or moon, and that the glory of Yehova will illuminate the City of New Jerusalem.  Awesome!!

These details establish this speculation:
If the entrances are guarded by angels, to prevent anything from entering that would defile it, does that mean there are people outside New Jerusalem?

And if there is no sun or moon, because the glory of Yehova will illuminate the City, does that mean it will be dark outside of the City?
Is that what outer darkness is?
Outside the City of New Jerusalem?
Outside of the presence of the Glory of Yehova?
Is that where people are who are thrown into outer darkness?
Is this eternal, or only for a time?
We know there is weeping and gnashing of teeth associated with outer darkness.

Is it possible to make it into the kingdom of heaven, but to not be allowed into the City of New Jerusalem?
Is that what it means to be “least in the kingdom of heaven”?

Matthew 5:19
¹⁹ Whoever therefore breaks one of the least of these commandments, and teaches men so, shall be called least in the kingdom of heaven; but whoever does and teaches them, he shall be called great in the kingdom of heaven.

I am not claiming to fully understand these things.
Is my speculation correct, or way off base?
I don’t know.

But I do know this:
1. We do not want to end up in outer darkness.
2.  We do not want to aim to be least in the kingdom.

We are to do this instead:
Matthew 22:37
³⁷ Yeshua Messiah said to him, “‘You shall love the Lord your God with all your heart, with all your soul, and with all your mind.’ ³⁸ This is the first and great commandment.

How do we love Him?
He defines it for us:
John 14:15
“If you love Me, you shall keep My commands.”
John 14:21
“He who possesses My commands and keeps them, it is he who loves Me. And he who loves Me shall be loved by My Father, and I shall love him and manifest Myself to him.”
John 15:10
“If you keep My commands, you shall stay in My love, even as I have kept My Father’s commands and stay in His love.

OK, let’s restate Matthew 22:37, using the definition of love that Messiah provided to us:
³⁷ Yeshua Messiah said to him, “‘You shall keep the commandments of the Lord your God with all your heart, with all your soul, and with all your mind.’ ³⁸ This is the first and great commandment.

Is this how we avoid outer darkness?
By doing what Messiah says to do?
By loving Him the way He tells us to?
I don’t know about you, but I’m on board.
Right or wrong?
Don’t care.
How can it hurt to love Him the way He says to?
Pray on these things.
Do not find yourself in outer darkness one day…

2Peter 2:20-21
 For if, after they have escaped the pollutions of the world through the knowledge of the Lord and Savior Jesus Christ, they are again entangled in them and overcome, the latter end is worse for them than the beginning. ²¹ For it would have been better for them not to have known the way of righteousness, than having known it, to turn from the holy commandment delivered to them.

Have I answered any questions, or just created more?
In the end, let’s take a look at the Greek words used for outer darkness in scripture:

G1857 – ἐξώτερος – exōteros
Strong’s definition:  exterior:—outer.

However, Thayer’s Greek Lexicon tells us this:
ἐξώτερος, ἐξωτέρᾳ, ἐξώτερον (a comparative from ἔξω, cf. ἐσώτερος, ἀνώτερος, κατώτερος), outer: τό σκότος τό ἐξώτερον, the darkness outside the limits of the lighted palace (to which the Messiah’s kingdom is here likened), Matthew 8:12; Matthew 22:13; Matthew 25:30. ((the Sept.; Strabo, others).)

Wow, that is exactly what I’ve speculated above.
Maybe I am on to something…

G4655 – σκότος – skotos
Strong’s definition:  shadiness, i.e. obscurity (literally or figuratively):—darkness.

Outline of Biblical Usage:
-darkness; of night darkness
-of darkened eyesight or blindness
-of ignorance respecting divine things and human duties, and the accompanying ungodliness and immorality, together with their consequent misery in hell
-persons in whom darkness becomes visible and holds sway

I don’t know if this article solidly answers any questions about outer darkness.
But here is what I’m going to do:  I’m going to strive to be greatest in the kingdom, not least in the kingdom.
Will you join me?