This paper provides an analysis data on the aesthetic experiences (Aguirre, 2004) and usages of the Media and the Internet described by 12 young men (14 - 19 y/o) in relation to their self-identification and socialization as gay (Troiden, 1989; Orne, 2011). The data was drawn from a face-to-face semi-structured interview of each teenager during the year 2013 in Pamplona (Spain). Following analysis of the interviews which draws on a queer theoretical approach, the paper also offers guidance for schools and families based on the research findings. Following Foucault (2008) and Butler (2010), this paper studies how the teenagers’ first experiences of homosexuality were queer and trans/homophobic stigma (Herek, 2004). Memories of their recent childhoods and school days inform of how they learned to reject and fear it and eventually, via the Media and the Internet, understood that to self-identify and socialize as gay was a legitimate possibility. Teenagers described meaningful experiences of gay-media-and-cyber affiliations (Dhoes & Simons, 2012; Gomillion & Giuliano, 2011) as well as queer reading practices (Lipton, 2008). On one hand there were direct and positive identifications with openly gay male characters and celebrities but also different levels of rejection towards them and other representations depictured/perceived as stigmatized. On the other hand there were examples of ‘diva fandom’ (Click, Lee & Holladay, 2013), homoerotic gazing and other escape attempts through entertainment (Dyer, 2002) involved in their gay-identifications and coming-outs. From the current debates among teachers, scholars and activists in Spain (and in other European countries) emerge two approaches to increasing positive attitudes towards sexual and gender diversity in education: the inclusion and anti-bullying discourses and practices, and the queer transformation of school. However, the findings of this research point out that both are relevant and that a pragmatist approach (Aguirre, 2004), which cares for aesthetic experiences, could help to develop a holistic education for all.