For Dilthey, as for many intellectuals of his time, it is no more possible, after the kantian criticism in ontology and the growth of the historical consciousness, to give an absolute credence to the validity of synthetic metaphysical systems neither to the large cosmological, psychological and theological tales. But Dilthey is not a “post- metaphysical” philosopher. The aim of this paper is to show, by contrast and comparison with Franz Rosenzweig and Karl Löwith’s writings, that for Dilthey, the tragic element in the structure of the human life can be thought under two main aspects. The first is an epistemological one, concerning the historical and geographical limitation of the points of view, the transcendentals not only in the intellectualist Kantian meaning but on top of that in the vitalist Diltheyian meaning. It can be partially treated with the descriptive method and the narrative form of the sciences of mind. The second aspect is an existential one, inherent to the ambivalence, the contingency and the finitude of the individual life. Remedies to this last are the hermeneutical methods of the others individual lives.