During this time in Jesus' ministry, many of the Pharisees, who were experts in the Law, wanted to catch Jesus doing something that goes against the law. They often question Jesus' motives and words because their culture has suggested that whoever knows the most and seemed to follow the law the best is the greatest.
While the disciples were constantly with Jesus and supported His teachings, they sometimes had questions, too that they hadn't yet understood. So when the disciples pose this question, they're curious about what Jesus will say because His teachings are usually at a much higher level of understanding than their's.
Jesus answer is fascinating - I'm sure it was even more fascinating then, but it's still fascinating today. During these times, most of the Pharisees and those being led by them wanted to make sure they were no longer bringing curses on their people by sinning against the law that God gave them. The goal during this time was to follow every law as closely as possible and to stay away from those who don't. Therefore, they believed that those who had the most knowledge of the law ought to be the most blessed in the kingdom of heaven.
I think what Jesus wanted to accomplish here was to redeem their sense of wonder. Jesus is trying to show them that those who believe they have studied and learned every detail about the law and the coming Messiah are the very ones who are missing it. No one can actually fathom God's wonder and glory - even those who know every detail of Scripture and law. Jesus wants them to return their heart to a place of wonder and innocent curiosity in who He is so that he can get to know them.
I think it's important to say that I don't think Jesus would tell anyone not to study Scripture and not to learn as much as they possibly can about Him. I think He's trying to shake us out of the mindset of gaining knowledge to understanding a Friend. He wants to wow us and fascinate us - and He should. He can do unfathomable things and sometimes He may even do it just to see the wonder in His children's eyes. The example I think of is when parents take their children to Disney World when they're only about 4 years old. Many people will say, "That's crazy. It's so much money and the kids will never even remember it." But the parents aren't taking them just to instill some sort of long-term memory in their child - they're doing it because seeing their child come alive with wonder is absolutely price. It awakens something to their souls that no memory can compare to. I think this is what God wants to do for us in all areas of our lives. He wants to lavish His love and riches on His children just because He loves us.
- Michele Houston