This chapter analyses Simmel’s intellectual explorations during his middle period (ca. 1900 – ca. 1910). Having despaired of the possibility of finding a grand synthesis, Simmel developed a radically pluralistic vision of the world, in which no comprehensive unity was envisioned, but each particular form of experience served as a symbol of unity. This view formed in his mind as he engaged with the ideas of Schopenhauer and Nietzsche. The chapter examines Simmel’s attempts to find a symbol of unity in the aesthetic and religious experience, as well as in the experience of femininity. These explorations, however, did not bring about any general philosophical solution. In the end, none of these experiences was shown by to be a fully satisfactory answer to the discontents of modernity.