During the past decade or so, much HCI research has, according to many researchers, become increasingly phenomenologically oriented. Some have gone so far as to argue that HCI is now in a phenomenological paradigm. But how does such a paradigmatic view work for understanding interaction in the ever growing sphere of social media? Prima facie it may look as it would work only well since social media has become increasingly richer in terms of the sheer range of phenomenologically possible user experiences provided by new and emerging interaction technologies. However, through a critical reading of three major phenomenological works in HCI, we argue that phenomenology as traditionally applied in HCI points indirectly to alternative approaches for engaging in much of contemporary social media research due to its associated semiotic and relationally oriented contents. One possible family of approaches for analyzing such content can be found, as we will argue, in poststructuralist theory. We propose an increased engagement with poststructuralist semiotics grounded in Jacques Derrida’s philosophy and exemplify how this could contribute to the study of social media in the context of HCI.