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The term “losing oneself” is among those concepts, like “intoxication, restlessness and wishlessness”, which have been repeated so many times in Rumi’s poems. They are contrasted with “being oneself”, restfulness, sobriety and wishfulness. The difference between what Rumi understands of these words and their contemporary meaning is of importance here. Today, what we perceive of their meaning is something experienced, rational and related to modern psychology and psychoanalysis, all of which are alien to perceptual, lingual culture of Rumi’s time. We are to survey the secret meanings of these words, which are typically set together in his poems, through his two major masterpieces, Divan-e-Shams and Masnavi-e-Ma’navi. In this Study we will gradually appreciate the inter-connection between these words and other terms in Sufism like annihilation, persistence, predestination, freedom, rapture, attraction, ecstasy etc. Finally, through this examination we will understand the meaning of art which also differs from what is discerned as cotemporary fine art.