In this work, we address the challenges of designing interactive technologies that approach menstruation in a positive way. Building on a Research through Design approach, we underline the tensions emerging from first-hand experiences and reflections in a design workshop. In order to maintain a positive approach, rather than asking participants what problems they encountered while on their period, we asked them what desires they had, and what experiences might help them cope with it. The results of the workshop emphasized the need for reflecting critically on how we perceive menstruation when designing and how viewing menstruation as a problem might perpetuate taboos and distance women's experiences from their bodies. We aim to contribute to the ongoing discussion on designing for women's health in HCI by suggesting implications for researchers and practitioners.