Before the question can be answered completely let us begin to look at the references to outer darkness within the context of what was said in total. In the first case in Matthew 8, the centurion knowing the extremes of Jewish purity concerns acknowledges the authority of Jesus to command healing even from a distance. To this the Lord responds"
"Verily I say unto you, I have not found so great faith, no, not in Israel. And I say unto you, That many shall come from the East and West, and shall sit down with Abraham, and Isaac, and Jacob, in the Kingdom of Heaven. But the children of the kingdom shall be cast out into outer darkness; there shall be weaping and gnashing of teeth." Matthew 8:10-12
Here the conversation is about something that happens in this world, people come from the East and West who are not part of the Chosen People. The confusion comes when they are pictured as set down with Abraham, Isaac, and Jacob. The reader should remember that those who died in faith prior to the Lord's death were ushered into the place called Abraham's Busom or Paradise, and those who are saved after the Lord's death are pictured by Paul in the Book of Ephesians as already seated with Christ in Heavenly places immediately upon salvation, even before death. It is quite easy to understand the passage concerning the children of the kingdom being cast into outer darkness as the condition of separation or spiritual darkness that came upon them for the sake of the Gentiles after the rejection of Christ as Messiah. There certainly has been much weeping and gnashing of teeth in the two thousand years that have since passed.
Let us now look at the second reference in Matthew 22. In chapter 21, the Lord has predicted the loss of the privileges to the Children of Israel, and in particular the false religionists, the Pharisees, along with the general invitation to all men, "whosoever falls on this stone..." The passage makes it clear that they knew exactly who He was talking about. After that the Lord Jesus Christ makes the parable of Matthew 22. Let us look at it in its entirety:
"The Kingdom of Heaven is like unto a certain king, which made a marriage for his son., And sent forth his servants to call them that were bidden to the wedding and they would not come. Again, he sent forth other servants, saying, Tell them which are bidden, Behold, I have prepared my dinner: my oxen and my fatlings are killed, and all things are ready: come unto the marriage. But they made light of it, and went their ways, one to his farm, another to his merchandise: and the remnant took his servants, and entreated them spitefully, and slew them. But when the king heard thereof, he was wroth: and he sent forth his armies, and destroyed those murderers, and burned up their city. Then saith he to his servants, the wedding is ready but they which were bidden were not worthy. Go ye therefore into the highways and, and as many as ye shall find, bid to the marriage. So those servants went out into the highways and gathered together all as many as they found, both bad and good: and the wedding was furnished with guests. And when the king came in to see the quests, he saw there a man which had not on a wedding garment: And he saith unto him, Friend, how camest thou in hither not having a wedding garment? And he was speechless. Then said the king to the servants, Bind him hand and foot, and take him away, and cast him into outer darkness: there shall be weeping and gnashing of teeth. For many are called but few are chosen." Matthew 22: 2-14
What this passage looks like is a parable that encompasses the entire spectrum of time from the preaching of the Kingdom through the Church Age to the Marriage Supper of the Lamb. In the Church Age both good and bad are bid to come, but some seek to come in despising the ways of God. The illustration seems to make it plain that in neither age can one enter in without coming by the way appointed. You will remember the Church is granted the privilege of being clothed in white garments and this person has none indicating they have sought entrance without being part of the true believers. Remember that wheat and tares have grown together to the end. Remember this is an earthly picture of a spiritual reality. I would not say this is something occurring in heaven, because I do not see the Bible as being specific concerning where the Marriage Supper will take place. A parable is a picture, like a drawing, not an exact reproduction as in a photograph. The outer darkness in this case could be a picture of Tartarus, the lowest deepest depths of hell where the darkness itself serves to bind.
Finally we come to Matther 25. Here we have the well known parable of the unprofitable servant, otherwise known as the parable of the talents: I will not read the whole passage into the text in this case because it is so well known. Suffice it to say that this passage is distinct from the preceding two because it is about a servant who has not used wisely what his master entrusted to him. This does not mean he is not a servant, but he is not a servant who has been profitable. In this case he has something in common with many in Israel who believed but did not have works or actions based upon belief. At the time the servants are making an accounting of how they have used what God has given them there are two possible conclusions available. The first is that this is an ongoing accounting that occurs when the believer meets with the Master. In this case the penalty of outer darkness could be a symbol of being spiritually cut off from further enlightenment, or it could be at the time servants are tried for reward at the end of the age, in which the passage should be seen to have a corresponding relationship with 1Corinthians 3: 11-15. In this case you do have the experience of loss in eternal reward without the loss of salvation if one has not used properly those things entrusted to him. You will notice that the servant is not bound. We could compare it to the reference in chapter 8 except for the fact that statement is general and not individual.
The word skotos is a rather general word for darkness and can be used in comparative such as the difference between being in sunlight and in shade. The word skotos is used in the Scripture to desribe blindness and the darkness upon the land at the time of the Lord's death.Matthew 27:45 Outer is the word exoteros which adds to understanding the idea of distance from or perhaps out of the presence of. There is an error possible in presupposing as many have that these words have to mean the same thing or be speaking of the same thing all the time. An individual cannot appeal to the Law of First Mention in this case because this is not a theme that runs through the Scripture, but rather is confined to the teaching of the Lord about different facets of His Revelation in history, some of which is yet to come. I also think that people have done great disservice to the Scripture by adding the to outer darkness as has been done in certain modern texts. It leads people to presuppose that there is one outer darkness in the words of our Lord rather than each reference is relative to the subject.
Another point I would like to make is that it is an error to say there will be no tears in heaven. I need merely to point to Revelation 21:4, where God wipes away all tears to demonstrate there is a period of weeping in heaven. I think that is clear evidence that an unfruitful servant can have his time to experience grief without loss of salvation.
Finally I want to share with you that in modern translations there has been a tendency to add the word "the" as "the Outer Darkness" which would imply not a general expression but a specific one. The translators of the KJV were correct to omit this and leave each reference to stand alone. What is accomplished in these modern versions is to throw confusion into what the Word of God means.
When we seek to discover the true meaning of any passage of Scripture and the conclusion we come to is in contradiction with the clear meaning of other Scripture, there is evidence that something is wrong for God does not have contradictions in His word. I congratulate you in refusing to be satisfied with any interpretation that is in contradiction to other Scripture.
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