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Turn 35 (or 40, as the case may be) and just stop giving a shit whether other people think you're cool or not.You don't need to turn any age to do this - when you get to 40, though, the effort of caring about your coolness quotient just gets to be too much bother.
buy an ipod to fill the hollow void in your soul.Actually, this is the closest some of us can come to coolness - Now that I finally had the void in my soul filled via a Christmas present, I feel ever so slightly cool on the train. Either that, or it helps me to just turn the world off and be myself to myself, which is the only way to be truly cool, after all.