It is commonly acknowledged that Western modernization has changed the outlook on identity, from the ascribed identity in premodern times to the identity management in the late-modern times. The medium of the Internet facilitates a relatively open exchange between positions that are not bound by time and space, resulting in a more tentative self-construction. Regardless of its specific sociohistorical format, every self-construction and identity formation may consist of cycles of intensified “selving”. Dante’s divina commedia is a poetic account of the author’s journey through hell, purgatory, and heaven. Dante is a forerunner of modernity in questioning his own identity through introspection and a critical soul searching. At the same time, the Divina Commedia is a period document in its extensive use of doctrines, metaphors, and symbols that allude to a medieval Christian worldview with its closed and preordained cosmology. The Internet has created a cyberspace with an unlimited stock of virtual contexts to explore.