Empathy has been linked to music preferences in controlled laboratory settings, but naturalistic settings like music streaming platforms remain unexplored. This study investigates how trait empathy influences music preferences and sequential listening behaviors in real-world settings. To this end, we collected and analyzed one-year Spotify listening histories of 290 Indian university students alongside their trait empathy scores, measured using the IRI scale. Our results reveal that individuals who score high on the IRI subscales of Empathic Concern, Fantasy, and Perspective Taking prefer sad music. Moreover, those scoring high on Empathic Concern or Perspective Taking were found to be more likely to transition from happy to sad music. These findings partially align with previous lab-based research, specifically for the subscales of Empathic Concern and Fantasy, while providing novel insights into the relations between the Perspective Taking subscale and music consumption. The study also provides novel insights into sequential listening behaviours, thus, strengthening the evidence that empathy shapes musical preferences and listening behaviors across diverse contexts.