This brief essay considers the three papers of the special issue of Interacting with Computers by Picard and colleagues, from several perspectives. First, I question two aspects of the work: the Computers Are Social Actors (CASA) approach, and the use of psychophysiological measurements of emotion without a stated theory of emotion. Despite these criticisms, the contributions of Picard and colleagues are valuable and powerfully challenging. I suggest three convergent ways of to pursue this important research program. I am grateful to Gilbert Cockton for the privilege and responsibility of commenting on the ground-breaking papers in Interacting with Computers by Rosalind Picard and associates (Klein, Moon, and Picard, 2002; Picard and Klein, 2002; Schreirer, Fernandez, Klein, and Picard, 2002). Although in many ways preliminary, their research calls us to reflect on the formal study of emotional interactions as conducted with and through computers, which until now have largely “reflect[ed] a view of the user as part of a productivity equation” (Picard and Klein, 2001). This is an original, provocative, and important challenge. As Cockton reminds us (2002), this work requires us to reconsider many of our theoretical and practical ideas about what emotion is, how it happens, and what we may want to do about it as we continue to do research and design with computers. In a similar vein – but with a very different methodology – Gaver and Martin (2000) have challenged what they call the “simple dichotomy between work and play” that can cause “[m]any devices [to] import values from the workplace into the home, emphasizing the requirement of ‘domestic work’ by allowing chores to be done more efficiently or productively.” McCarthy (2001) elaborates on some of these ideas in his argument to move from an HCI based in function to an HCI of “enchantment,” emphasizing delight, with overtones of magic. In another related development, Monk and colleagues have proposed alternatives to what Cockton has criticized (2002) as the “usability hardcore” approach to HCI, through a series of conferences called Computers and Fun (Computers and Fun, 1998, 2001).