Once Upon a Time is about these encounters of diaspora and the displaced ‘homeland’ and describes a personal tale of my own diaspora and traveling culture, which crosses the boundaries of nation-states and is located in between different geographical places. Through this film work I explore a historical interpretation of the term ‘diaspora’ but also try to further explore and conceive the term in relation to more recent forms of migration and transcultural experience. I look at the 16 ‘diaspora’ through a transcultural comparison in a Lusophone postcolonial context, delineating the relationship of my own diaspora group, ancestral homeland and countries of present residence. I recognize that the relations of a diasporic group are presently not only aligned with their country of actual residence and their ancestral homeland but have been blurred with many other diasporas and cultures.