Using digital technology, in particular social media, is often associated with envy. Online, where there is a tendency for people to present themselves in their best light at their best moments, it can feel like we are unable to turn without being exposed to people living out their perfect lives, with their fancy achievements, their beautiful faces and families, their easy wit, and wide social circles. In this paper, I dive into the relationship between envy and digital technology. I offer an enriched account of envy that aims to establish both the situated nature of envy, as well as (more controversially) the possibility of self-envy. I explore how features of digital technology not only increase the frequency with which we might experience envy directed at others, but also envy directed at other versions of one’s self. For online, we not only encounter idealized versions of others but digitally idealized versions of our selves. Moreover, I argue that digital technology does not only increase the likelihood of experiencing self-envy but makes the experience less cognitively onerous. I conclude by considering how current digital technology shapes what we envy.