Matt. 13:50 says, “In that place there will be weeping and gnashing of teeth” (ESV). The word, “weeping,” from klauthmos, means, “to weep or wail, with emphasis upon the noise accompanying the weeping.” (Louw-Nida)
Have you heard people who wept loudly? That is the weeping of the wicked in hell. It is a loud emotional expression of crying. It is like the weeping of a girl who has lost her boyfriend. She weeps as if there is no other boyfriend left in the world. Well, you don’t need to weep as if he is the last guy on earth. It may well mean that God has somebody better for you.
Now why would the wicked weep and gnash their teeth in hell? Some people think that hell is a fun place to go on sinning.
I read a story of a man who dies and goes to hell. Satan greets him (he’s the usher there!), shows him three doors, and says, “There are three doors here. But choose only one door. Inside that door, you will spend the rest of eternity. Now choose.”
The man opens the first door, and sees people standing on their heads on a wooden floor, looking very uncomfortable. He opens the second door, and sees people standing on their heads on a concrete floor, looking even more uncomfortable. Finally, he opens the third door, and sees people standing around chatting and drinking coffee, up to their knees in garbage and filth.
“Hmmm,” he says, “that looks bad, but it’s better than the other two. I’ll take the third door.” Satan smiles and shows him in.
Ten minutes later Satan walks back into the room and says, “Alright, coffee break’s over, everyone back on your heads!”
Seriously, to the Jews, hell is never a fun place.To them, hell is the place of fiery judgment. Jesus taught that hell is the fiery furnace. In this fiery furnace, unbelievers are forever removed from the presence of God due to unbelief. They are forever excluded from the kingdom of God.
Thus, in the Parable of the Net, the wicked shall weep and gnash their teeth in hell, because they have put themselves outside of the kingdom of God. By their unbelief, they have removed themselves in effect from the light of Christ. They have excluded themselves from the kingdom of God.
The act of loud weeping by the wicked, then, expresses a feeling of anguish, agony, and misery over their eternal punishment. They are thrown into the fiery furnace. They are cast into outer darkness. Consequently, they shall weep and gnash their teeth in hell. The realization of their punishment brings a feeling of pain and anguish, resulting to the acts of weeping and gnashing of teeth.
The act of weeping connotes anguish. But the act of gnashing of teeth connotes anger—“anger at self, God, and others for this horrific judgment.” It signifies anger towards God for removing them from the righteous in the kingdom. It indicates anger towards God for rejecting them. The gnashing of teeth shows anger towards God for judging them.
The kingdom of God is like a net that draws in all the wicked and all the righteous. When the net of God’s kingdom shall be filled, Christ shall come. When Christ comes, there shall be a separation of the wicked. Hell shall be the destination of the wicked. Weeping and gnashing of teeth shall be the expression of the wicked.
The pulling of the net is imminent, with the soon coming of Christ. Are you a follower of Christ? Jesus taught the Parable of the Net to the disciples, not to unbelievers. It should therefore encourage us to be faithful to Christ. It should assure us of the certainty of judgment of the wicked.
Are you a non-follower of Christ? Will you come to Christ now, while there is still time? Come to Christ today, and he will be your Savior. But if you do not come to Christ today, he will be your Judge tomorrow.
 D. G. Burke, “Gnash,” in The International Standard Bible Encyclopedia (Vol. 2; rev. ed.; ed. Geoffrey W. Bromiley; Grand Rapids: Eerdmans, 1986), 483.
 Frederick Dale Bruner, Matthew: A Commentary—Vol. 2: The Churchbook, Matthew 13-28 (rev. ed.; Grand Rapids: Eerdmans, 2004), 542; cf. W. D. Davies and Dale C. Allison, Jr., A Critical and Exegetical Commentary on the Gospel According to St. Matthew (vol. 2; London: T & T Clark, 1991), 31.