The next debate focuses on the people Jesus surrounds himself with, tax collectors and sinners. He even called Levi, a despised tax collector, to be one of his disciples; this meant leaving behind everything he knew to follow Jesus. To celebrate their newfound friendship, Levi threw an extravagant feast for all the guests--including other tax collectors and those labeled "sinners." The Pharisees and scribes were outraged, pointing out that Jesus' reputation was being compromised by the company he kept. Although the Pharisees held Levi and his friends contemptuously, Jesus was not ashamed to dine with them. Jesus explained that just as a doctor visits those who are ill to help them recover, his mission was not to save the righteous but sinners instead.

Jesus's words on repentance prompt an inquiry. The Baptist's disciples appear to be repentant because their behavior mirrors the Pharisees' followers; however, the presence of eating and drinking from Jesus's group set them apart. He explains that his arrival has initiated a messianic banquet - it would not be appropriate to fast while he is here. Upon his passing, then they will fast accordingly.

To explain his point, Jesus tells a parable: it would be foolish to patch an old piece of clothing with a new one because the materials will not match, and the fabric will tear. Similarly, His message of spiritual renewal cannot fit within the existing framework of Pharisaic tradition. The new wine proclaimed by Jesus is incompatible with the old wineskins. The Pharisees' outdated traditions are no match for the revolutionary teaching of Jesus. Our Savior's mission to rescue sinners necessitates a massive change for those who think they're righteous because they are Jewish and follow the law.

In Luke 6:1–5, we encounter the initial Sabbath dispute. After catching Jesus' followers plucking and consuming grain on a holy day, the Pharisees leveled an accusation against them for breaking the law. Jesus referenced a similar incident with David in 1 Samuel 21:1–6 as proof that his disciples were within their rights to do this action. Jesus' second Sabbath dispute is displayed in 6:6-11, where he cures a man with a withered right hand while teaching at the synagogue. His miraculous act was motivated by his inquiry about whether doing good on the Sabbath would be acceptable.

Ascending a mountain, Jesus prayed all night before choosing the twelve—similar twelve tribes of Israel. With prayer and reflection complete, He determined His followers: from Simon Peter to Judas Iscariot. These men were chosen to be more than just disciples; they are His messengers and helpers in ministry who will spread his message far and wide.