My introductory essay discusses some of transculturalism’s enduring conceptual challenges from the perspective of the history of German cultural and political theory. I am particularly interested in the discursive space between Immanuel Kant’s individualism and Johann Gottfried Herder’s and Moses Mendelssohn’s concepts of cultural identity. My hope is that such a discussion can enrich some of our current questions, such as: Have culture studies placed too much emphasis on difference, rather than on commonality? Can a renewed interest in the cosmopolitan individual surpass the privileged position of academic or upper-class internationalism? Can concepts of transculturality avoid the pitfalls of homogenizing politics or overstretched individualism? After mentioning a few challenges to current conceptions of transculturalism that may arise in the wake of recent developments in the natural sciences, I end my remarks with a brief example of a possible intersection of literary studies and science. The essay engages three topics: (a) the question of culture; (b) transcultural participation; and (c) transcultural empathy and the sciences.