This paper describes a new digital technology to support emotional self-awareness and empathy, called G.I.R.L.S (Girls Involved in Real Life Sharing). The system invited users to reflect actively upon and interact with a dialogue about how the story made them feel through the construction of pictorial narratives. In a pilot study with teenage girls, the system enabled the subjects to express themselves freely in a comfortable and meaningful way, and fostered an increase in emotional expressivity as compared to a control group. While the system has been tested with a small group of minority middle-school children, a web version of the system is in development that we believe will be useful for school counselors. (Contains 3 figures and 1 table.)