Socially assistive robots are being designed to support people's well-being in contexts such as art therapy where human therapists are scarce, by making art together with people in an appropriate way. A challenge is that various complex and idiosyncratic concepts relating to art, like emotions and creativity, are not yet well understood. Guided by the principles of speculative design, the current article describes the use of a collaborative prototyping approach involving artists and engineers to explore this design space, especially in regard to general and personalized art-making strategies. This led to identifying a goal: to generate representational or abstract art that connects emotionally with people's art and shows creativity. For this, an approach involving personalized "visual metaphors" was proposed, which balances the degree to which a robot's art is influenced by interacting persons. The results of a small user study via a survey provided further insight into people's perceptions: the general design was perceived as intended and appealed; as well, personalization via representational symbols appeared to lead to easier and clearer communication of emotions than via abstract symbols. In closing, the article describes a simplified demo, and discusses future challenges. Thus, the contribution of the current work lies in suggesting how a robot can seek to interact with people in an emotional and creative way through personalized art; thereby, the aim is to stimulate ideation in this promising area and facilitate acceptance of such robots in everyday human environments. © 2021 Cooney.