Summary: Some say they will obey God and don't, Others resist, then go. The Jews in Jesus day did not think they had to obey Jesus so they did not go to work in the vineyard. No serving when you should is a failure.
The Ones “Go” and The Ones Who Don’t “Go” Kelly Durant
Matthew 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 my vineyard.’ 29 He answered and said, ‘I will not,’ but afterward he regretted it and went. 30 Then he came to the second and said likewise. And he answered and said, ‘I go, sir,’ but he did not go. 31 Which of the two did the will of his father?” They said to Him, “The first. ”Jesus said to them, “Assuredly, I say to you that tax collectors and harlots enter the kingdom of God before you. 32 For John came to you in the way of righteousness, and you did not believe him; but tax collectors and harlots believed him; and when you saw it, you did not afterward relent and believe him.
2. How many of you have ever asked someone to go to the store for you. You tell them, here is $20 so go and buy bread, milk, peanut butter, and eggs. And then what happens? They come back only with peanut butter, jam, and bread and then they tell you they did not have money for the rest of the things? So you have coffee without milk that day!
And there are other people you give them $20 to buy just bread and they buy it but then they do not return the $15 change! Both of these cases make you a bit angry right? These cases happen frequently and these are people who fail in their mission. These people who cannot show their selves to be faithful in the small things. This makes you think they would not be faithful in the bigger things, right? Luke 16:10 He who is faithful in what is least is faithful also in much; and he who is unjust in what is least is unjust also in much.
Some people are like in Proverbs 25:19 Confidence in an unfaithful man in time of trouble Is like a bad tooth and a foot out of joint. I know if I see a person fail a few times in doing a simple job, I no longer count on them to do a job, and this is a Biblical standard to live by.
3. What was the point of Jesus concerning the two sons in the verses today? The first application applies to the context in which he was speaking which was to the Jews in His audience. But this principle applies to all! The reason Christians affirm scripture is living is because it is timeless and it can be applied to one certain circumstance, and then it can also be applied to other circumstances in our current day.
In this first context Jesus is addressing the previously chosen ones back then, the Jewish people. He is pointing out God had a mission for the Jews, to obey or to “go work in God’s vineyard” and they, for many years already claimed to be doing God’s will but in the end they were not. Going to do God’s will infers obeying God’s commands as He defines them, and Jesus taught clearly, and that is to love God and their neighbors as their selves. If they were doing God’s will they would have recognized Jesus as God’s son and obeyed His commands as Jesus pointed out.