In this paper we answer the call for “designing for an attractive ageing” by designing for social interaction of senior citizens within their local community. In this vein, we present Walky, a design exploration through which we explored if, and how, augmenting the rollator that senior citizens use for walking could open up new opportunities for social interactions. A set of theoretical perspectives that include embodied interaction, the role of social interaction in ageing, and the phenomenon of microblogging, together inform Walky. We explored these theoretical perspectives in a particular situation of co-designing with senior citizens, and other skate-holders including the municipal corporation of Copenhagen. We explicate the process of sketching interactive artefacts that drove our exploration. We furthermore highlight how it was instrumental in engaging with the theory-situation dialectics in designing for social aspects of ageing. We contribute to the interaction design research community focusing on ageing suggesting to make the process of engaging with the theory-situation dialectic explicit as valuable knowledge for other researchers in the field. We support this suggestion by providing the example of Walky and its compositional whole as a demonstration of how we explored abstract theoretical perspectives in particular design situations leading to three concrete designed artefacts.