Analysing select episodes of HBO’s High Maintenance (2016–2020), adapted from a Vimeo web series of the same name (2012–2015), the following chapter examines how the series’ roots in ‘Indie TV’, combined with its mumblecore influences, its anthological form and character perspective, heighten its potential as a vehicle for empathy for a generation often negatively regarded on television—namely millennials. The chapter highlights the show’s complex relationship with empathy and human connection and demonstrates that the series uses the figure of protagonist The Guy (Ben Sinclair) as conduit and witness to elicit but also to teach compassion and empathy to viewers.