Abstract This article examines the language mixing practices of Puerto Rican adolescents in various social media platforms through a framework of code-mixing and socioindexicality. Over a twelve-week period, I collected samples of online text messages from six island bilinguals of an elite community of practice (CofP) and studied the way their unique socializations in private schools and bilingual universities contributed to the ways they made sense of languages, their social meaning potentials, and uses across online interactions. Against the meaningful backdrop of colonial-dynamics of Spanish and English in Puerto Rico, the paper examines how ideologies of “nationalism” and “race” get reproduced or challenged through bilingual practice, and English takes up an equally important role for the construction of social identities in the interactions of youth. Additionally, the study discusses bilingual styles that have been enregistered as social styles specific to technological mediums of communication and youth registers, Puerto Rican netspeak, as well as emerging social styles that indicate queer gender identity, or non-binary practices. In this sense, I offer a description of the island bilingual that is dynamic, strategic, and metapragmatically conscious of the purist ideologies of Spanish in Puerto Rico, as well as the indexical potentials of appropriating variable gender forms in Spanish, bilingual language practices, and netspeak registers towards the negotiation of identities in technological interaction. The way bilinguals relate to the languages at their disposal can provide a window to impending questions on the perceived coloniality of English, potential changes in language ideologies and uses, and whether and how language policies may shift to meet current demographic attitudes and language uses of contemporary Puerto Ricans.