Design materials are defined as a combination of what they are, what they do, and the ways they interact with other materials. In this pictorial, we explore the interactions between machine learning (as a design material) and another design material—the human face—in the form of digital portraiture. Employing an exploratory Research through Design approach we consider how machine learning simultaneously enriches and subverts the materiality of the human face. Through a combination of images and text, we offer some considerations and provocations for further research.