This artistic-scientific study explores the role of perception, interpretation, and expectation in contemporary portrait photography, with a particular focus on the smiling portrait. By combining insights from neuro-aesthetics, philosophy, and Predictive Processing theory with photographic experiments and interactive installations, the research questions the apparent transparency and readability of facial expressions (in particular) and photography (in general). In contrast to traditional views that directly link a smile to happiness, this study posits that meaning is a dynamic and contextually determined construct. Through manipulations, sequential image series, and textual interventions, “prediction errors” are generated that disrupt and enrich the viewing experience.