With the advent of affective computing and physical computing, technological artefacts are increasingly mediating human emotional relations, and becoming social entities themselves. These technologies on one hand prompt a critical reflection on human-machine relations, and on the other hand offer a fertile ground for imagining new dynamics of emotional relations mediated by technology and materiality. This chapter describes design research drawing on theories of technology, materiality and making. Carried out through fashion and experience design, the practice amplifies the processes of mediation. By creating material playgrounds for technological and human agency, the experiments described here aim to generate knowledge about the emotional self, critical reflection on human-machine relationships, and new imagined emotional relations resulting from the hybridity of humans and technology.