Seated side by side, the “born digital” Generation Z’s devices endlessly connect. Thumbs tapping incessantly, how frequent/effective is their face-to-face communication? Michikayan and Suaráez-Orozco (2016) argue that “adolescents and young adults use social media for self-presentation and self- disclosure” (Michikayan and Suaráez-Orozco, 2016, p.114). The ubiquitous selfies, and subsequent postings thereof, suggest that this self-presentation and self-disclosure is visual as well as verbal. As Rutledge (2013) notes, these “are not meant to stand alone as a single message or withstand the passage. Selfies … represent a personal experience that is also social, taken for the express purpose of sharing.” In the virtual space, Joseph Beuys’s democratic axiom “everyone is an artist” applies because of open access to visually mediated presentation of self. Enabled by contemporary digital, networked technology and social media, young people engage in creative activities to express their sense of self in ways that are changing learning and interaction towards affinity-based, socially networked peer participation. Not influenced by their digital world, they are, as Michikayan and Suaráez-Orozco (2016) observe, “creators - actively and interactively constructing their identities, establishing, re-connecting, or defriending relationships”. This study uses a technologically negotiated social/academic environment in which to explore visually mediated presentations of self by Gen Z college and high school students from two different cultures in the context of data regarding technological comfort zone and negotiation strategies; art and technology preferences; and consumption habits. Presentations were initially paired and then shared in open groups to investigate how students initiate cross-cultural dialogue and transform the space into a “virtual learning community” which is interactive and explorative. Results suggest that Gen Z students experience cognitive and affective dissonance between their acknowledged necessity for digital connectedness and the need for direct interaction (for example, face-to-face verbal communication, direct hand/eye technologies - drawing, photography). The thesis explores implications for visual arts and other educators, including professional learning. It demonstrates the potential and also the challenges of mediated communication when students’ socialisation, learning and art making converge.