Socially assistive robots could contribute to fulfilling an important need for interaction in contexts where human caregivers are scarce–such as art therapy, where peers, or patients and therapists, can make art together. However, current art-making robots typically generate art either by themselves, or as tools under the control of a human artist; how to make art together with a human in a good way has not yet received much attention, possibly because some concepts related to art, such as emotion and creativity, are not yet well understood. The current work reports on our use of a collaborative prototyping approach to explore this concept of a robot which can paint together with people. The result is a proposed design, based on an idea of using visual metaphors to convey contingency and artistry. Our aim is that the identified considerations will help support next steps, toward supporting positive experiences for people through art-making with a robot.