This article looks at the notion of what, not who, is underserved in museum education. The importance of looking through, in, and from objects in order to uncover underserved questions and themes is vital. A willingness to consider new ways to approach collections and display is necessary to have a dialogue with our audiences about how museums can be relevant and best serve their needs. I argue that how we research, display, and discuss works of art creates openings for new historical insight and contemporary relevance. Using an upcoming exhibition focused on the representation of slavery in 18th-century portraiture as a case study, the following themes will be explored as strategies for opening space for the underserved subjects in our pictures and the underserved questions of our audience: (1) unfreezing the past, (2) recognizing scenes of subjection, (3) converting absence to presence, and (4) seeing the flexible history of objects.