A variety of approaches have emerged in HCI that grapple with the ineffable, ill-defined, and idiosyncratic nature of aesthetic experience. The most straightforward approach is to transform the ineffable aspects of these experiences into precise representations, producing systems that are well-defined and testable but may miss the fullness of the experienced phenomenon. But without formal models and codified methods, how can we design and evaluate for a phenomenon we aren't sure can be adequately captured? In this article, we present a case study of a system for reflection and awareness of emotional presence that was, in a sense, lived into being. Through system design, use, and evaluation we recount how the system evolved into something that enhanced rather than impoverished the sympathetic awareness of another. In discussing the strategies and results of the case study, we examine what it means for the HCI community to not only design for aesthetic experiences but also bring aesthetics into the practice of HCI.