This qualitative study offers a novel exploration of the links between social media, virtual intergroup contact, and empathy by examining how empathy is expressed through interactions on a popular social media blog. Global leaders are encouraging individuals to engage in behaviors and support policies that provide basic social foundations. It is difficult to motivate people to undertake such actions. However, research shows that empathy intensifies motivation to help others. It can cause individuals to see the world from the perspective of stigmatized group members and increase positive feelings. Social media offers a new pathway for virtual intergroup contact, providing opportunities to increase conversation about disadvantaged others and empathy. We examined expressions of empathy within a popular blog, Humans of New York (HONY), and engaged in purposeful case selection by focusing on (1) events where specific prosocial action was taken corresponding to interactions on the HONY blog and (2) presentation of people in countries other than the United States. Nine overarching themes; (1) perspective taking, (2) fantasy, (3) empathic concern, (4) personal distress, (5) relatability, (6) prosocial action, (7) community appreciation, (8) anti-empathy, and (9) rejection of anti-empathy, exemplify how the HONY community expresses and shares empathic thoughts and feelings