Ideas That Do Not Square with the Christian Faith: "Coolness"
That's not to say a Christian can't, in the end, be branded as "cool." Some are, and that's fine. But it is to say that a Christian should not pursue coolness. A Christian should not seek to be a social alien in his culture, but he should not go to the opposite extreme and seek to be culturally cool. The core of Christianity is not image. It's truth. The pursuit of cool is bound up with the pursuit of an image. One buys the right things, says the right things, and goes to the right places, all so that one can construct an image. In one sense, of course, we all play some part in constructing our image. But I think a Christian should do so as un-self-consciously as possible, to write badly.
Christians do not desire image. We desire heaven. While we don't seek to be freakish in a social sense, we are also those who know ahead of time how much coolness matters in the end. Unlike the world, we realize that it will all vanish away at the extinguishing of our lives, and then it will never again matter, not for a single thread of a second. Coolness and image are two ideas (closely bound together) that have no place in heaven. Everyone will be mature in heaven, and so in actuality there won't be a cool group. There will only be people as they are, people who worship Christ, not people who have constructed an image.
Being culturally aware can help us to make initial connections, but we should not deceive ourselves and think that coolness is what draws people to Christ. If people are drawn to communities that emphasize cultural relevance, and if they stick and become Christians, I'm guessing that the primary reason they did so was not because the church's members listened to the right songs or wore the right clothes. I'm guessing it was because they saw authentic faith, actional faith, that loved them as they were and told them good news of salvation. We can deceive ourselves, I think, such that we think the trappings, the accessories, are the substance. They are not. Trappings may on some level help us to have more fluid initial conversations, but when it gets down to it, lost people will desire to know us better based on whether we make an attempt to understand them, to listen to them, and to love them. I play basketball and am aware of cultural media, but I realize that connection to these things simply helps me to connect with certain people better in an initial sense. It doesn't guarantee fruitful witness or conversion on their part. Love and truth, however, do, when the will of God so desires. So even if you're not terribly relevant to today's youth generation, so long as you seek to love them and earnestly connect with them, you'll be fine. You'll also save yourself some loss in the day when the heavens and earth are recreated. Coolness, you see, like your possessions, is going to pass away, and we will never see it again.