Explaining the parable of the two sons - Matthew 21

In Matthew 21 we read:

Matt. 21:28 “But what do you think? A man had two sons, and he came to the first and said, ‘Son, go work today in the vineyard.’
Matt. 21:29 “And he answered, ‘I will not’; but afterward he regretted it and went.
Matt. 21:30 “The man came to the second and said the same thing; and he answered, ‘I will, sir’; but he did not go.
Matt. 21:31 “Which of the two did the will of his father?” They said, “The first.” Jesus  said to them, “Truly I say to you that the tax collectors and prostitutes will get into the kingdom of God before you.

Jesus gives us the answer to your question. The first son did the will of his father. 

That son initially disobeyed the word of his father by refusing to go into the field, but later he repented and obeyed. In the end, he did the will of his father and the father’s word was obeyed. His earlier refusal was sin, but the father was willing to accept the son’s repentance and allow him to serve anyway. So the son was credited with doing the will of the father in the end. 

The second son did not do the will of his father, though he agreed to. His agreement was a lie, and his failure to go was evidence that he never truly intended to do the father’s will. So not only did the second son fail to obey the word of his father, but he also lied about his intentions, which showed him to be a hypocrite. 

Jesus makes the application: He says this second son was a picture of the hypocritical Pharisees (whom Jesus was speaking to in v.31), who claimed to do the will of the Father in Heaven yet who didn’t obey the word of God. These men would not be in the Kingdom of God, Jesus says, while lessor Jews like prostitutes would be in the Kingdom because though they disobeyed the Lord through their sinful lifestyles, in the end they repented and accepted Jesus as Messiah, which resulted in their forgiveness.

So the first son pictures sinners who, by repenting and obeying the Gospel, will enter the Kingdom. While the second son pictures hypocritical, self-righteous religious leaders who talk about serving God but actually live in disobedience to the word of God.

Let us be like the first son!

Scripture quotations taken from the (NASB®) New American Standard Bible®, Copyright © 1995, 2020 by The Lockman Foundation. Used by permission. All rights reserved. www.lockman.org