The aging society has arrived, and more and more older adults are living in a nursing home. However, institutional care settings are often described as places where residents suffer from social isolation. Under this context, we describe the process of translating into fieldwork into interactive systems facilitating elderly residents’ social interaction and wellbeing. Comprehensive semi-structured interviews with older residents and caregivers were first conducted in a Dutch nursing home, aiming at understanding the status of their social interaction. The context of a typical elderly resident’s social interaction was then generated, and based on which three interactive systems focusing on different aspects of their social interaction were designed and deployed. The paper finally concludes with design considerations for promoting social interaction and wellbeing of older adults living in the nursing home.