Do Prostitutes Go to Heaven? (Matthew 21:28-32). Outline.

Jesus said to them, “Truly I tell you, the tax collectors and the prostitutes are entering the kingdom of heaven ahead of you” (Matthew 21:31b).

• “Assuredly, I say to you that tax collectors and harlots enter the kingdom of God before you” (NKJV).
• “This is true to say to you: The tax agents and the prostitutes go ahead of you into God’s Empire” Scot McKnight. The Second Testament: A new translation.

1. The setting: To whom is Jesus speaking (Mt 21:23)? Why did they question his authority (Mt 21:9-10, 12-13, 15)? What prompted Jesus to tell the this [and the next 2] parables (Mt 21:24-27, 32, 38-39; 22:4, 5-6)? 
• Who does the father and the two sons represent in this context (Mt 21:28a, 31, 32; Lk 15:1-2)?
• What does this parable teach about the difference between words and promises, and actual obedience?
2. Why is the word "today" significant in the father's command to both his sons (Mt 21:28b, 30a; Heb 3:7-8, 15; Ps 95:7ff)?
• Are you more prone to be upfront with God about your resistance (Mt 21:29a), or do you pretend to be compliant while internally refusing to obey (Mt 21:30)?
• Have you promised to obey God [said, "I go, Lord"], but have not actually done so today (Isa 29:13; Mt 15:8; Jas 2:14)?
• Has God called you to "change your mind" (repent) and start obeying, even if you have said "no" in the past (Isa 55:7; Ac 3:19)? [...for instance with a specific sin, or relationship...]
• Are there "outcasts" in your life or community that you are tempted to look down on? Does this parable challenge you to see them as potential candidates for God’s Kingdom? [cf. the religious leaders looked down on "tax collectors and prostitutes."]
• Is there an area of your faith that has become so familiar or routine that you have stopped listening to what God is actually saying to you today? [cf. the religious leaders knew the Scriptures and the prophecies about John the Baptist, yet they refused to believe.]
3. How does this parable connect with the larger themes of authority, repentance, and entering the kingdom of God?

Outline:

I.    Jesus' Person (1:1-4:16).

II.    Jesus' Proclamation (4:17-16:20).

III.    Jesus' Passion (16:21-28:20).

Outline (Matthew, R. T. France. NICNT--The New International Commentary on the NT):

I. Introducing the Messiah (1:1-4:11).
II. Galilee: The Messiah revealed in word and deed (4:12-16:20).

* The Messiah's authority revealed in his teaching: The Discourse on Discipleship (5:1-7:29). SoTM.

* The Messiah's authority shared with his disciples: The Discourse on Mission (9:35-11:1).

* The Kingdom of Heaven: The Parable Discourse (13:1-53).

III. From Galilee to Jerusalem: The Messiah and followers prepare for confrontation (16:21-20:34).
IV. Jerusalem: The Messiah in confrontation with the religious authorities (21:1-25:46).

* Living Together as Disciples: The Discourse Relationships (18:1-19:2).

* The End of the Old Order and the Reign of the Son of Man: The Discourse on the Future (24:3-25:46).

V. Jerusalem: The Messiah rejected, killed, and vindicated (26:1-28:15).
VI. Galilee: The Messianic mission is launched (18:16-20).