Social isolation and loneliness among older people is a growing problem with negative effects on physical and mental health. In co-creation with older adults individualized social activities were designed where older adults through computer mediated communication were able to participate in social activities without leaving their homes. Four types of activities were designed; outdoor activity, music event, visiting a friend and leisure activity. A participatory action research design was applied, where end users together with scientists from two research fields developed, tested and evaluated online participation in the activities. Usability and safety of the systems were major concerns among older adults. The evaluation pointed out that level of simplicity, usability and audio-video quality determined the level of satisfaction with the human interaction during the activity, thereby affecting the meaningfulness of the activity. The research presented in this paper constitutes the first step in a long-term research process aiming at developing a digital coaching system that gives older adults personalized support for increasing participation in meaningful social activities.