Here's a powerful quote from Tim Keller's book The Prodigal God.
“[In every example in the New Testament] when Jesus meets a religious person and a sexual outcast (Luke 7) or a religious person and a racial outcast (John 3-4) or a religious person and a political outcast (Luke 19), the outcast is the one who connects with Jesus and the elder-brother type does not. Jesus says to the respectable religious leaders 'the tax collectors and the prostitutes enter the kingdom before you.' (Matthew 21:31)
“Jesus’ teachings consistently attracted the irreligious while offending the Bible-believing, religious people of his day. However, in the main, our churches today do not have this effect. The kind of outsiders Jesus attracted are not attracted to contemporary churches, even our most avant-garde ones. We tend to draw conservative, buttoned-down, moralistic people. The licentious and liberated or the broken and marginal avoid church. This can only mean one thing. If the preaching of our ministers and the practice of our parishioners do not have the same effect on the people that Jesus had, then we must not be declaring the same message that Jesus did. If our churches aren't appealing to younger brothers, they must be more full of elder brothers than we'd like to think."