This paper examines second-year social work students’ (n = 19) reflections on empathy as part of an interpersonal skills course at a regional university in Australia. Students were asked to consider their personal, online and classroom experiences, before responding to a reflective learning prompt: ‘Online communication is killing connection: (the Facebook Like symbol) does not equal empathy’. Qualitative analysis of their responses identified tensions between students’ engagement with social media and their developing understandings of empathy. Students reported an ease and confidence in the use of social media, but were also aware of the risks associated with perceived anonymity, shifting boundaries and an absence of audial and verbal cues in establishing context and quality of communication. Their reflections also suggested that the range of stimulus material used in the interpersonal skills course—including podcasts—had increased their social media awareness and their desire to improve their online interpersonal skills. The implications for professional and pedagogical objectives, as well as curriculum design are discussed.