In May 2014 the first ever Gay Pride Parade was held with tremendous success in Cyprus, a society that is still by-and-large very conservative. At the same time, in an adjacent street, the powerhouse that is the Greek Orthodox Church, organised a counter-parade comprising of far-right individuals, nuns and priests which, both in terms of numbers and influence, failed spectacularly. This paradox spurred a wave of analyses and examination of the way in which Cypriot society and culture seem to be changing until today, 7 years later, engaged as it would seem in a queering process, as well as on issues such as gay activism and civil partnership. My article analyses the ways in which the Parade’s expressed queer desire and the participants’ performativity starting in 2014, gesture towards a significant socio-political change in Cyprus. This analysis is largely based on Deleuze and Guattari’s notion of desire as a machine that generates reality, as I approach the Parade’s “queerness” as an expression of Cypriot society’s polyvalent socio-political manifestations which intentionally include the disenfranchised and provide new answers to questions of belonging. It is ultimately argued that, the way in which performative imagination seems to be able to generate reality, gestures towards a better understanding of the weak points of a dominant structure, becoming thus much more influential than the way in which Michel Foucault understands the notion of “power”. In other words, that the participants’ actions, choices and played-out desires lead to a final, dual performance that is the Parade and the counter-parade on the “stage” that is Cyprus. The Parade’s cultural performativity then, can be read as a site of vital performances, a kind of Bakhtinian carnivalesque that can lead to an understanding of a new socio-political identity which entails hope for the future. Thus, the dynamics of non-heteronormative sexual identities in Cyprus and their political potentials are explored vis-à-vis their capacity to interrogate hegemonic discourses, all of which gestures towards the queering of Cypriot culture.