Jesus’ first reference to weeping and gnashing of teeth comes in where He compares the kingdom of heaven where “many” come from all parts of the world to “recline at the table with Abraham, Isaac and Jacob.” The sons of the (other) kingdom, however, are thrown into “outer darkness” where there is weeping and gnashing of teeth, a description of a truly horrible and painful fate.
But the children of the kingdom shall be cast out into outer darkness: there shall be weeping and gnashing of teeth. ( Matthew 8:12 )
In His parable of the weeds sown in the field, Jesus again describes the fate of those who reject Him, this time adding to the description “the fiery furnace” into which they will be cast.
The Son of man shall send forth his angels, and they shall gather out of his kingdom all things that offend, and them which do iniquity;
And shall cast them into a furnace of fire: there shall be wailing and gnashing of teeth.
( Matthew 13:41-42 )
The story of the guest who comes to the wedding feast of the Lamb without the proper clothing (salvation) is cast into outer darkness where there is weeping and gnashing of teeth
And when the king came in to see the guests, 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. ( Matthew 22:11-13 )
and then there is Matthew 24:44-51 which brother Ramon posted already.
For the kingdom of heaven is as a man travelling into a far country, who called his own servants, and delivered unto them his goods.
And unto one he gave five talents, to another two, and to another one; to every man according to his several ability; and straightway took his journey.
Then he that had received the five talents went and traded with the same, and made them other five talents.
And likewise he that had received two, he also gained other two.
But he that had received one went and digged in the earth, and hid his lord's money.
After a long time the lord of those servants cometh, and reckoneth with them.
And so he that had received five talents came and brought other five talents, saying, Lord, thou deliveredst unto me five talents: behold, I have gained beside them five talents more.
His lord said unto him, Well done, thou good and faithful servant: thou hast been faithful over a few things, I will make thee ruler over many things: enter thou into the joy of thy lord.
He also that had received two talents came and said, Lord, thou deliveredst unto me two talents: behold, I have gained two other talents beside them.
His lord said unto him, Well done, good and faithful servant; thou hast been faithful over a few things, I will make thee ruler over many things: enter thou into the joy of thy lord.
Then he which had received the one talent came and said, Lord, I knew thee that thou art an hard man, reaping where thou hast not sown, and gathering where thou hast not strawed:
And I was afraid, and went and hid thy talent in the earth: lo, there thou hast that is thine.
His lord answered and said unto him, Thou wicked and slothful servant, thou knewest that I reap where I sowed not, and gather where I have not strawed:
Thou oughtest therefore to have put my money to the exchangers, and then at my coming I should have received mine own with usury.
Take therefore the talent from him, and give it unto him which hath ten talents.
For unto every one that hath shall be given, and he shall have abundance: but from him that hath not shall be taken away even that which he hath.
And cast ye the unprofitable servant into outer darkness: there shall be weeping and gnashing of teeth. ( Matthew 25:14-30 )
All these references to weeping and gnashing of teeth have one thing in common—the undeniable fact that those who do not belong to Christ will suffer this terrible fate, while His children will enjoy bliss in heaven with Him forever In heaven.
And God shall wipe away all tears from their eyes; and there shall be no more death, neither sorrow, nor crying, neither shall there be any more pain: for the former things are passed away.
( Revelation 21:4 )
The pain that causes the gnashing of teeth will be unknown in heaven, and there will be no weeping, no wailing and no tears. The sorrow and death that cause us to weep and mourn will be a thing of the past. Sickness, death, persecution, and sin will be no more.