Although research has shown that older nursing home residents can benefit from caring relationships with nurse aides, few studies have explored their dyadic, evolving relationship dynamics. Using a dyadic perspective, this study simultaneously explores caring relationships among older residents and nurse aides in Shanghai. In a government-sponsored nursing home in Shanghai, 20 matched resident–nurse aide dyads participated in semi-structured, in-depth interviews (N = 40). We performed thematic analysis to interpret and conceptualise the evolving caring relationships within dyads. Four types emerged during the evolution of caring relationships across the 20 dyads: (a) sharing strong rapport, (b) respecting each other, (c) hesitant responding, and (d) keeping emotional distance. Upon placement, all the residents kept emotional distance from nurse aides, and their assigned nurse aides provided care-giving by following nursing home regulations. As time passed, nurse aides began to create a family environment and tried to interact with residents on an emotional level; however, residents’ attitudes varied. The caring relationships in some dyads evolved as rapport and respect emerged, while others remained hesitant and distant. This suggests that residents and nurse aides prioritised caring relationships differently in terms of autonomy preservation and safety protection, respectively. This study sheds light on nursing home practice to facilitate building caring relationships between residents and nurse aides.