COVID-19 heightens awareness of and sensitivity to the contingencies, elusiveness and pain attached to how intimacy is playing out in digital communication technology. Certainly, popular discussion on how digital technology achieves or fails to achieve closeness predates COVID. However, the pandemic has lifted the emotional politics of digital communication platforms from their background of mundanity and daily use. I draw on my COVID-specific experiences of online dating and virtually witnessing the death of a family member. Sex and death are continually rescripted by emerging technologies that expand and reshape different forms of connection. Sex and death were my most confronting experiences with COVID-era digital intimacy, which is not surprising given that COVID provides the context in which the digital and some of life’s more intense experiences are enmeshed. This essay traces some of the alienating, humorous and close experiences of digitally mediated intimacy in COVID.