The phrase I always tell them, you wont do it specifically doesn't strike me as the words of the helpful, skeptical voice of reason, but perhaps I'm reading too

The phrase I always tell them, you wont do it specifically doesn't strike me as the words of the helpful, skeptical voice of reason, but perhaps I'm reading too much into a careless phrasing. It sounds to me like the words of a superior know-it-all douchebag, not the hard-nosed, skeptical advice of a worthwhile friend. YMMV.