Technological developments have led to an improvement in the quality of life in the Western world and, consequently, have contributed to the widespread ageing of the population. In this context, devising support strategies for older adults is increasingly relevant and challenging. Considering that social interactions are essential for the quality of life of older adults and that, in Portugal, this demographic group widely uses television, the ProSeniorTV system was conceptualised. This proactive, gamified system is integrated into television and is capable of notifying, motivating, and rewarding users for participating in social events organised in their area of residence. A prototype of the system was subjected to a one-month field trial with the collaboration of twenty senior participants, aiming to assess its effectiveness in motivating older adults to participate in social events. Daily use of the system effectively increased seniors’ motivation to participate in social events while also helping to reduce their levels of loneliness and isolation. Thus, the proposed system proved to be a powerful tool for promoting new social habits and fostering more active and healthy ageing processes.