“But the subjects of the kingdom will be thrown outside, into the darkness, where there will be weeping and gnashing of teeth.” Matthew 8:12

“They will throw them into the blazing furnace, where there will be weeping and gnashing of teeth.” Matthew 13:42

“…and throw them into the blazing furnace, where there will be weeping and gnashing of teeth.” Matthew 13:50

 “Then the king told the attendants, ‘Tie him hand and foot, and throw him outside, into the darkness, where there will be weeping and gnashing of teeth.’” Matthew 22:13

“He will cut him to pieces and assign him a place with the hypocrites, where there will be weeping and gnashing of teeth.” Matthew 24:51

“And throw that worthless servant outside, into the darkness, where there will be weeping and gnashing of teeth.’” Matthew 25:30

“There will be weeping there, and gnashing of teeth, when you see Abraham, Isaac and Jacob and all the prophets in the kingdom of God, but you yourselves thrown out.” Luke 13:28

            Jesus used this phrase once in Luke and six times in Matthew.  He used it to describe the people in hell and how they responded to the separation they were experiencing there.  They are put in a place of darkness and eternal fire, which indicates a place of no hope, no light, no God, filled with ashes and worthlessness.  

            Luke indicates a moment of seeing the possibility that one could have—a relationship with those who influenced the kingdom—and yet be thrown out of their presence.  That’s painful.

            Weeping and gnashing of teeth indicate despair, regret, loneliness, worry, all of them emotional sadness that continues forever.  Why would anyone want to go to such a place?