This paper seeks to examine the role of the official and "de facto" languages of anglophone Caribbean islands such as Jamaica. In reflecting on their statuses as users of language, tertiary level students registered in a Year One Performing Arts Program provided much insights into the interplay of both languages that coexist in society and provide the referent point in the construction of Caribbean linguistic and cultural identities. The role of popular theoretical linguistic claims in understanding language attitudes and acquisition challenges provided much insight and contemplation. Post Primary Schools as fertile grounds to establish centers for needs driven language instruction were explored as a viable approach to language learning in Post Primary language Instructions.