In this paper we explore the feasibility and design challenges in supporting co-located and virtual social interactions in residential care by building on the practice of reminiscence. Motivated by the challenges of social interaction in this context, we first explore the feasibility of a reminiscence-based social interaction tool designed to stimulate conversation in residential care with different stakeholders. Then, we explore the design challenges in supporting an assisting role in co-located reminiscence sessions, by running pilot studies with a technology probe. Our findings point to the feasibility of the tool and the willingness of stakeholders to contribute in the process, although with some skepticism about virtual interactions. The reminiscence sessions showed that compromises are needed when designing for both story collection and conversation stimulation, evidencing specific design areas where further exploration is needed.