The paper investigates Dilthey’s hermeneutic conception of understanding with regard to the question of the human sciences (Geisteswissenschaften), and analyses his path-breaking work as the first elaboration of a dualistic account in philosophy of science. Although not having reached a satisfying version of his approach, Dilthey opened with the distinction between natural sciences and human sciences an ongoing discussion on the unity or plurality of what might be called “science”. I follow in the paper how Dilthey developed in his later writings a hermeneutics designed to give epistemological foundations for human sciences. Afterwards, I explore the work of Dilthey by relating it to the philosophical hermeneutics of Hans-Georg Gadamer which can be analyzed partly as continuation, partly as critique of Dilthey’s philosophical project. I shall argue for the claim that Gadamer gives a deeper image of human sciences, while renouncing to grasp them in terms of their scientific character.