Will there really be gnashing of the teeth?

The answer is yes and no. Yes because Jesus said so himself. No because the lake of fire is the second death/everlasting death.  

In the accounts where the phrase "weeping and gnashing of the teeth" is used Jesus is shown to be giving illustrations

Matthew 13:36"Then after dismissing the crowds, he went into the house. His disciples came to him and said: “Explain to us the illustration of the weeds in the field.”

Matthew 13:40 "Therefore, just as the weeds are collected and burned with fire, so it will be in the conclusion of the system of things."

Matthew 13:53 "When Jesus had finished these illustrations, he departed from there."

Matthew 13:50"and will cast them into the fiery furnace. There is where their weeping and the gnashing of their teeth will be. 

Matthew 13:53 "When Jesus had finished these illustrations, he departed from there."

Matthew 13:51"“Did you get the sense of all these things?” They said to him: “Yes."[Jesus asked them if they understood his illustrations]

Matthew 13:53 "When Jesus had finished these illustrations, he departed from there."

So what really is the weeping and gnashing of the teeth?

In a nutshell, weeping and gnashing in this case represents the condition of those who lost out on a valuable gift or something of importance, which is accompanied by grief and frustration(except you don't have emotions when you're dead).Ecclesiastes 9:5, 6,.. Imagine you are going to an amusement park tomorrow, you leave at 10 in the morning. All you have to do is wake up early enough to catch a ride with your friends. The previous night, you decide you're gonna stay up late to watch a series of YouTube videos. Since you went to bed late, you end up waking up late and miss your ride. At home is where your weeping and gnashing of the teeth will be.

Remember that there was a Parable about a Marriage Feast that was the source of the phrase weeping and gnashing of the teeth. Also another similar parable about  Master trusting his employees with money. To read these parables, scroll to the bottom of this page. 

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Matthew 22:1-14
1. Once more Jesus spoke to them with illustrations, saying:2  “The Kingdom of the heavens may be likened to a king who made a marriage feast for his son. 3  And he sent his slaves to call those invited to the marriage feast, but they were unwilling to come. 4  Again he sent other slaves, saying, ‘Tell those invited: “Look! I have prepared my dinner, my bulls and fattened animals are slaughtered, and everything is ready. Come to the marriage feast.”’ 5  But unconcerned they went off, one to his own field, another to his business; 6  but the rest, seizing his slaves, treated them insolently and killed them.7  “The king grew wrathful and sent his armies and killed those murderers and burned their city. 8  Then he said to his slaves, ‘The marriage feast is ready, but those invited were not worthy.9  Therefore, go to the roads leading out of the city, and invite anyone you find to the marriage feast.’ 10  Accordingly, those slaves went out to the roads and gathered all they found, both wicked and good; and the room for the wedding ceremonies was filled with those dining.11  “When the king came in to inspect the guests, he caught sight of a man not wearing a marriage garment. 12  So he said to him, ‘Fellow, how did you get in here without a marriage garment?’ He was speechless. 13  Then the king said to his servants, ‘Bind him hand and foot and throw him into the darkness outside. There is where his weeping and the gnashing of his teeth will be.’14  “For there are many invited, but few chosen.”

Matthew 25:14-30

For it is just like a man about to travel abroad who summoned his slaves and entrusted his belongings to them.i15 He gave five talentsa to one, two to another, and one to still another, to each according to his own ability, and he went abroad. 16 Immediately the one who received the five talents went and did business with them and gained five more.17 Likewise, the one who received the two gained two more.18 But the slave who received just one went off and dug in the ground and hid his master’s money.a

19 “After a long time, the master of those slaves came and settled accounts with them.j 20 So the one who had received the five talents came forward and brought five additional talents, saying, ‘Master, you entrusted five talents to me; see, I gained five talents more.’k 21 His master said to him: ‘Well done, good and faithful slave! You were faithful over a few things. I will appoint you over many things.l Enter into the joy of your master.’m 22 Next the one who had received the two talents came forward and said, ‘Master, you entrusted two talents to me; see, I gained two talents more.’n 23 His master said to him: ‘Well done, good and faithful slave! You were faithful over a few things. I will appoint you over many things. Enter into the joy of your master.’

24 “Finally the slave who had received the one talent came forward and said: ‘Master, I knew you to be a demanding man, reaping where you did not sow and gathering where you did not winnow.o 25 So I grew afraid and went and hid your talent in the ground. Here, you have what is yours.’ 26 In reply his master said to him: ‘Wicked and sluggish slave, you knew, did you, that I reaped where I did not sow and gathered where I did not winnow? 27 Well, then, you should have deposited my moneya with the bankers, and on my coming I would have received it back with interest.

28 “‘Therefore, take the talent away from him and give it to the one who has the ten talents.p 29 For to everyone who has, more will be given, and he will have an abundance. But the one who does not have, even what he has will be taken away from him.q 30 And throw the good-for-nothing slave out into the darkness outside. There is where his weeping and the gnashing of his teeth will be.’