AI-assisted art creation allows every user to generate artistic expression that matches their worldview and preferences. Even those with little or no artistic ability can now engage in the process of creating an artistic representation, including the natural empathetic exercise involved. We propose that this empathy has potential to increase a sense of personal connectedness both to the target being represented by the art, and to the online community (OC) to which the art will be contributed. We propose an experiment wherein users will use AI to generate a portrait representing a deceased relative, and contribute it to an OC.