Why did Jesus spend time with the Pharisees?
Like any other story, one will read the story of the Bible and instantly have a "most hated character." While you're reading through Exodus, it might readily be Pharaoh. While you're reading through David's story, it might be Goliath.
And then you get to the gospels, and you'll know that many people will instantly hate the Pharisees. They're legalistic know-it-alls who got the disciples in trouble and got on Jesus's nerves all the time.
But have you ever wondered why Jesus would spend so much time with them? Sure it was the Pharisees who followed Him all the time, but Jesus could have chosen to ignore them. But why did Jesus choose to interact with them and even take his precious highly demanded time to entertain their questions?
We can learn a few things from Jesus's interactions with these antagonistic characters, and how Jesus had bigger plans for them than we think.
He made an example out of them
Many of Jesus's most valuable insights came from exchanges with the Pharisees, Sadducees, keepers of the law and experts. Jesus looked at these small and big debates and saw the opportunity to minister to anyone who was listening.
The Pharisees needed to hear the truth, too
Not all of the Pharisees were against Jesus. There were some who became followers of Christ, just like Nicodemus, who was not just a Pharisee but a key member of the Sandhedrin, too.
Legalistic and judgmental people need the love of Christ just as much as "sinners" do, and maybe even more in some instances. Jesus was ready to break their shallow mindsets and readily present grace and love to them.
God loves all people, even the legalistic
Why would Jesus share God's love with the Pharisees? Because the Pharisees were sinners too, and Jesus came to die for them as well! Jesus said in Mark 2:17, "Those who are well have no need of a physician, but those who are sick. I came not to call the righteous, but sinners."
And the Pharisees were sick with sin too, and Jesus loved them just the same. He just hated the character they were drenched in.
Their insecurity led to the cross
The Pharisees may have successfully sent Jesus to the cross, but that was all part of God's plan, too. Think about it: Without the insecurity and self-righteousness of the Pharisees, Jesus would have never been sent to the cross.
It just comes to show how God uses all circumstances -- both good and bad -- for His greatest will.