Much like music and other types of media in the past, technology has become the distinctive element separating generations: the definition of today's youth as "Digital Natives" only proves the importance that computer-based communication has taken within the identities of teenagers. The present paper aims at exploring how Social Media can become a stage for the enactment of "experimental identities" (cf. Ellison et al, 2006), allowing teens to gain the skills necessary to interpret social cues in both digital and real life (boyd, 2008). Given the permeation of the Internet within the social lives of the young, it seems relevant to focus on how Social Media can be used to make sense of one's identity in a time of drastic changes and transformations.