Social media fuel a sense of unsettledness to encourage uninterrupted connectivity and generate quantifiable engagement. This article is concerned with the habitual, naturalized character acquired by these platforms and with how this is paradoxically constructed by prompting a permanent state of anticipation. The aim here is to explore, with a phenomenological sensibility, the experiences that emerge in settings of continuous connectedness from the perspective of the people who use these technologies in the context of everyday life – that is, the ‘users’. Theoretically, the entry point is to revisit the claim of liveness – and its shifting relations with issues of sequential flow and eventfulness – and to position it as a central resource in this process, in which users are deliberately encouraged to expect the unexpected even in ‘non-eventful’ situations. Drawing from the thematic analysis of data collected through the diary-interview method with people who live in London and use a range of social media, I examine both how this urge of continuous connectedness operates and the ambivalent experiences it generates. The findings were categorized into five themes: excitement, anxiety, reassurance, fatigue, and responsibility.