David Hume was an undeniably brilliant philosopher who, at times, suffered in his writing the inability to adequately express his actual philosophy and thoughts. One of his most stunning arguments was, in actuality, a refutation of the Skeptics, a movement started in great part by Descartes, who attempted to convince Aristotelian philosophers that our experiences with the world are based solely upon our senses and, as such, our senses and thus our perception of the world and reality can be deceived. Therefore, the skeptic encourages us to question the validity of trusting only our senses for our knowledge of the world. While Descartes’ and the other Skeptics’ arguments were and continue to be the stuff of philosophical cliche (the `prove you exist` argument) the truth is that, as David Hume points out, there is no real point in pondering whether or not we actually exist. The fact of this futility is proven in the very real problem in that if we assume that the universe is the individual creation of just the `I`, then the very same person is also taking on the role of God, which, according to Hume and others like him, is an impossibility. The ultimate end of the Skeptics argument, if you follow it to its logical conclusion, is that it is possible that all of us are the creation of some one person’s imagination and that, as such, our existence is subject to the whims of one person’s perception of reality and the self. Hume’s argument, that such skeptical investigations of reality and the actuality of the self is pointless, is one which has a great deal of validity. But, there are counter arguments to his counter-argument, and in the interests of a full academic exploration of his philosophy, it is necessary to explore some of those arguments. It is the purpose of this paper, then, to examine three problems found in Hume’s argument and to demonstrate that the exploration of reality from a skeptical point of view is nothing more than an exercise of thought, one that can ultimately only lead lead to psychological diagnoses of breaks in sanity rather than a treatise on our actual reality.