Do you ask questions to learn or do you ask questions to support your position of what you already believe? When people want to be proven correct, they ask questions in such a way as to pull the answer they want. Trial lawyers are skilled in this kind of information gathering to support their case.
The Sadducees did not believe in life after death. They did not believe there is a resurrection of the dead. They put before Jesus the hypothetical situation of the woman who married six brothers successively because of widowhood, and yet left no heirs. “Whose wife will she be in the resurrection of the dead?” Hoping Jesus would say that is a moot question because there is no resurrection of the dead, the Sadducees got a surprise answer. We will be as angels then. Marriage is an earthly institution that does not exist in the resurrected life.
The Pharisees were passionate about ethics and the correctness of traditional teaching. Their question to Jesus was “What is the greatest commandment?” Of course Jesus knew the answer. However, knowing the motives of their hearts, Jesus asked, ‘Whose son is the Messiah?” According to the scriptures, David’s line is the chosen one. “How can the Lord be David’s son and David’s Lord at the same time?” This was a head scratcher. Son of David is in the flesh, and David’s Lord is in the spirit.
The Zealots were fervent anti-Roman activist. Their question to Jesus was whether they should pay taxes to Caesar. If Jesus said “no”, their cause against Rome would be bolstered. However, Jesus told them to respect the civil government as well as the religious government according to what was required as they were not in conflict.
The Essenes were passionate on communal living and purity laws. They brought the woman caught in adultery before Jesus looking for judgment and hoping for permission to stone her to uphold their cause. Jesus confronted them with their own sin and only extended mercy to her.
Through all these encounters, we see Jesus was interested in 1) eternal life, 2) relationship with the God, 3) honoring authority, and 4) mercy.
When we ask questions, are we interested in the same things Jesus is? Or we want to bolster our own opinions?