In view of increasing Globalization, Transnationalization and the growth of Transcultural spaces, it is important and interesting to study literature that encapsulates all the complexities of these phenomena. Issues like obliteration of cultural ‘Border’, analysing cultural complexities and the reshaping of hybrid realities of diaspora and globalization are becoming pertinent. This paper aims to study and interrogate such aspects in Gurinder Chadha’s film It’s a Wonderful Afterlife (2010). Chadha may be seen as a very relevant subject of study in the proposed context because of her own identity, especially as a diasporic filmmaker, and for the kind of movies she has made. Though aware of the nuanced concepts and theories of such contemporary fields of study, this paper draws mainly on the idea of ‘Transculturality’ as expounded by Wolfgang Welsch in his essay “Transculturality: The Puzzling Form of Cultures Today.” It can be noted that the cultural intertwinement portrayed in the movie amounts to a representation of ‘hybridity’, a near obliteration of cultural borders and that of the conflicts arising from such borders. The paper asserts this to be quite a representation of transculturality. But through a deeper analysis of various representations in the film, it has been argued that despite the obliteration of stringent traditional cultural borders and an increasing globalized/transcultural existence, there emerges a latent ‘Orientalism’. This is a ‘Re-Orientalist’ attitude that betrays the latest efforts of restructuring the postcolonial discourse in the era of modern diaspora, hybridity, global citizenship, and transnationality/transculturality etc. This also questions the ideological perspectives of the filmmaker who makes efforts to transcend borders but, in a way (even if unconsciously), circulates re-orientalist discourses/prejudices and reinstates postcolonial binaries which emerge as dangerous gaps in the progressive processes of transculturality and globalization.