Intimacy is conventionally associated with familiarity and comfort. Yet, within the temporal unfolding of intimate relations comes discomfort, ambivalences, breakdowns, and disruptions. My dissertation research builds on this critical and feminist understanding of intimacy and relations to design long-term and plural modes of intimate care technologies. I present three previous research projects that use discomfort as a resource for intimate technologies. These include affective discomfort, menstrual discomfort, and unhabitual movements. Inspired by feminist crip technoscience and feminist theories on materiality of bodies, I inquire how we could design intimate technologies that enrich long-term and embodied relationship with our own menstruating bodies. In my upcoming studies, I plan to investigate the potential of close-to-body shape-changing touch as a modality for generating situated bodily knowledge and fostering proactive self-care for menstrual pain.