Nicolas Bourriaud’s Relational Aesthetics (2002) provides a sophisticated critique of interactive aesthetics. His focus, however, is not literally interactive electronic art, but rather Conceptual Art of the 90s that deliberately reduces technical means and prompts human dialogic interaction. Bourriaud celebrates work that shifts the status of the art object from self-contained aesthetic thing to socially relational model (or field). In his view, technological art, in its very obvious claims to interaction reveals its association and complicity with broader regimes of simulated conviviality and interaction that characterize modern democratic society. It seems that interaction becomes all important in the instant that it effectively disappears. Here Bourriaud is clearly the heir to critics such as Adorno, Mumford and Baudrillard who question the social emancipatory claims of technological media. Despite its apparent Luddite tendencies, this critique retains value in terms of qualifying the rhetorical claims of electronic interaction. But for my purposes what is more interesting is the way in which Bourriaud draws upon key features of technological media in order to describe the sphere of genuinely critical interactive art. The digital image, for instance, in its programmatic, algorithmic potential provides a model for the contemporary art object. Rather than a static, fixed thing, the digital images represents a “generative power” (Bourriaud, 2002, p.70). I would argue as well that the notion of model itself reveals a debt to modern technological media, which constitutes not works but systems that obtain life and currency only through (problematic) interaction. Bourriaud’s critique represents an effort then to tease out a notion of genuine interaction from the formal structure of its avowed enemy. It is hardly surprising then that every positive aspect of dialogic interaction is defined in terms of its difference from electronic forms of interaction. Very curiously, the latter is positioned both as model and evil double for the properly relational character of contemporary art. This paper traces the contours of this ambivalent relation and considers the value of the concept of relational aesthetics towards an assessment of the interactive claims of interactive electronic art.