This article investigates the modern phenomenon of loneliness, recently exacerbated by the Covid-19 pandemic, through the lens of online digital music cultures. Using as a case study Annie Lennox’s 2020 YouTube video of Dido’s Lament, this article interrogates critically specific facets of online performance in mediating identity construction, in functioning as a digital archive of memory, and in partaking in social-technological entanglements that both exacerbate and alleviate human experiences of loneliness. The discussion further broaches the links between estrangement and alienation and the grief of ecological crisis, since this YouTube performance of Dido’s Lament comprises also one of Annie Lennox’s famous manifestos for tackling climate change. Drawing particular attention to technological, affective, experiential and (dis)embodied attributes of Lennox’s performance and its online context, the discussion considers how this performance can intervene both musically and non-musically as socio-political discourse and critique to some of the pressing issues it raises. The concept of digital liveness, as participatory and affective experience, is used to explore how this online performance creates new spaces for self-reflexivity in pursuit of alternative liminal experiences for both performers and listeners. Through the application of the concepts of internal focalization and performer-listener intersubjectivity, the discussion comments on the listener-spectator’s fluid positionality drawing attention to the performativity of empathetic acts of listening. By projecting poignantly shared loneliness as an inescapable modern condition, Lennox’s Dido, ultimately, promotes togetherness and communality as a means of living with liminality in times of crises. As a reflective afterthought, the article also posits the need to broaden the field of music performance studies in cross-disciplinary and culturally apposite ways that interrogate and respond to modern challenges, such as social loneliness, estrangement and the effects of digital consumerism on our environment, through the divulging of musical performances’ ambivalences and equivocations as legitimate forms of knowledge, being and relating to one another in times of socio-ecological precarity.