“How far is too far?” When I served in youth ministry, inevitably I would get this question from a brave teenager wanting to know about sex before marriage. While I did not want to discourage a genuine desire on their part to know how to remain righteous in their physical relationships with the opposite sex, I constantly felt a sense of frustration that they had entirely missed the point.
When we think about “right” and “wrong” avoiding a bottom line is not the heart behind any “thou shalt not.” The heart behind any “don’t” should always be a greater yes. Dietrich Bonhoeffer said, “The essence of chastity is not the suppression of lust, but the total orientation of one’s life towards a goal. Without such a goal, chastity is bound to become ridiculous.” Whether we are talking about sex, lying or any other “thou shalt not,” we need a greater yes to strive toward; a goal that is life-giving and good. We will not rationally say “no” to things unless we have that better “yes.”
When we (in contemporary American culture) talk about right/wrong, we think in terms of obligation to avoid certain laws or wrongs. The American ethic, we are led to believe, is that we should avoid those wrong things, but beyond that we are free to be whatever we want to be as a person. But, if that is the case, we have no reason for avoiding wrongs other than fear of punishment. Essentially, we are left, in America, with no great “yes.” To think that our only responsibility as humans is to avoid wrong things entirely misses the point (much like my teenagers).
Jesus offers abundant life (John 10:10) to those who believe. Yet, many Christians and Church-goers live a sad life that is characterized by anger over certain sins (homosexuality being the most prominent today). We have all seen fundamentalist (if that is a helpful term) churches where the totality of “the abundant life in Christ” is about avoiding those sins and speaking out against them. This misses the greater yes. But, I think there is an even deeper problem. The body of Christ represents God on earth; He displays Himself through His people. When the body of Christ only speaks to moral/spiritual issues, the unspoken assumption is that Jesus is irrelevant to everything else that happens on Earth. By doing so, they are missing the point: the greater yes. So, what is that greater “yes?” It is God Himself.
Jesus also said that eternal/good life is about knowing Him (John 17:3). In fact, Jesus goes so far as to say that living in that relationship is what causes us to live a full and flourishing life as humans (just read John 15). I have heard people take notice that Jesus spent more time chiding the Pharisees for avoiding the “thou shalt nots” and have even heard people site this as an example for Jesus’ rejection of organized religion. Jesus chided the Pharisees not because they were avoiding sin; after all, He demands that we be completely holy (Matthew 5:48 – a task we cannot do in our own power). Jesus chided the Pharisees not because they were “organized”; after all, it is He that founded the church. Jesus’ issue with the Pharisees was that they had missed the point: a relationship with God. While avoiding sins is good and necessary, it is not the point. The point is the greater yes that can only be found in a relationship with Christ.
By living in Him and following His ways, we will experience the abundant life that Jesus promises. If you are a Christian, I urge you to spend less time focusing on the “thou shalt nots” and more time encouraging people to be in relationship with the gracious and loving Jesus Christ. Why? Because anything else is missing the point.
JimHShultz.com 
I agree with you that if someone is asking a question such as “How far is too far?”, then they are missing the point entirely. However, I believe that Christian doctrine is just as much to blame for “we have no reason for avoiding wrongs other than fear of punishment” as American culture. Far too many Christians choose to follow doctrine for fear of judgement and not out of understanding. I think Christian religions need to move away from the whole heaven and hell deal (old testament) and more toward the teachings of Christ i.e. Love (new testament). If you have love in your heart, then you will end up obeying the 10 commandments by default.