In its emphasis on the feedback loops of top-down and bottom-up signal processing in the brain, and the exquisitely muddy area where they meet, the last century of psychology and neuroscience supports a model of aesthetic engagement wherein we meet the world halfway. As such, we ought to interrogate the apparati of our aesthetic engagements with equal fervor as we regard the pristine aesthetic objects themselves. In its unavoidable mustering of the totality of a person’s taste, expectation, and memory, as well as the social and political forces of the world around them, aesthetic engagement is thus far from a passive act. From traditions in art history that attribute creativity to the biographies of isolated geniuses to more recent offerings from neuroaesthetics that turn to the causative power of brain science, we explore several pitfalls of aesthetic engagement and interdisciplinarity, as well as possibilities for future avenues of inquiry that expand the engaged self to include more context.