Was either of the two sons in this parable blameless in regard to the father’s command? What was the fault of the first son? How is the blunt refusal of the first son to obey the father’s command like so many when first confronted with the gospel call to repentance? What does this son’s later regret teach us about our need to not give up hope on those who seem the most profligate and initially reject the gospel? For what reasons might the son have said he would not go work in his father’s vineyard? Cf. Luk 14:18-20. In what ways are the excuses people make for not giving heed to the demands of the gospel similar? Are we guilty of refusing to go work in the Lord’s vineyard because of our other interests and pleasures?
What was the fault of the other son? What is the significance that he even addresses the father as “sir”? Note that this is the same word translated most frequently as “Lord”; cf. Mat 7:21-22, 25:11, Luk 6:46. Is it also significant that the way he responded was with a terse “ego”—that literally has no verb, and means simply “I”. Cf. Luk 18:9-12, Rev 3:17. What does this parable teach us is understood to be more important not only in the eyes of God but also in the eyes of men: saying or doing? Cf. Mat 7:24-27, Rom 2:13, Jam 1:22. What does it also teach us is most important: where we begin or where we end up? Cf. Eze 18:24,27-28, Mat 10:22[1]. If we are to be blameless and pure children of God who are without fault, what does this parable teach us our two-fold response should be when the Father commands us to go work in His vineyard? Cf. Phil 2:14-15, Isa 6:8, Mat 4:19-22.
Consider that tax collectors were regarded by the religious Jews with the same contempt as the heathen Gentiles (Mat 18:17)—both of whom proved more repentant than the religious leaders of the Jews. Consider too that a harlot is one who offers her love in pretense and not in sincere faithfulness; in what way then did the religious leaders prove to be the true harlots, but the harlots proved to be the more faithful sons? What did Jesus say was the result of this in regard to the religious leaders? See Mat 21:31. What warning do these role reversals offer us today who are tempted to view with contempt “sinners” like homosexuals and fornicators, or those with piercings or who are tattooed, divorced, etc…? Cf. Luk 18:9-14. What should our attitude towards them be? See Luk 6:36-37, Eph 5:1-2; cf. Tit 3:3-6.
What does Jesus mean by “the way of righteousness” that John came to the people in? See Luk 3:8-14; cf. Gen 18:19. How is the way of righteousness the way of true wisdom, and how does it reflect the very nature of God and Jesus? See Pro 8:12,20, 22-31. What is the blessing of walking in that way? See Pro 8:32-35, 12:28, 16:31, Isa 35:8-10. Is this the only way that religious teachers or their followers may come? See Mat 7:13-15; cf. Pro 14:12. In this light, should the opposite of the way of righteousness necessarily be described as the way of evil, or also as the way of pretense? What is the danger of walking in that path when in our heart of hearts we know it is not the way of righteousness? See 2Pe 2:20-21. Can it now, or will it be said of us after our lives are over that we came in the way of righteousness or walked in that way? See Jer 6:16. As we stand at the crossroads and look, will we ask for the ancient paths and where the good way is and walk in it, or will we say, “We will not walk in it”?
What was it about the religious leaders that prevented them from believing the gospel when they saw its obvious results among the sinners who were turning to God in repentance; i.e., why were they unwilling to follow the tax collectors and harlots into God’s kingdom? Cf. Pro 16:18. How was the same true of the Jews in general—who were to be the first fruits among the nations of God’s kingdom—when they saw the results of the gospel among the Gentiles? See Act 22:21-22, Rom 9:30-10:3. What does this teach us about the importance of leaders leading in the way of righteousness, and the grave but deceptive consequences to them when they don’t? Cf. Luk 14:24 and think: Did the failure of the Jewish religious leaders to lead the nation in the way of righteousness prevent God from gathering fruit from among the Jews? Did the failure of the Jewish nation to lead in establishing the kingdom of God among the nations prevent God from establishing His kingdom among them? Can any man or nation’s disobedience frustrate the ultimate will of God? If we choose not to be a part of what God is doing, must God bend to our stubborn will or continue to cajole us because He has no other option? See Mat 22:8-9.