In this research, a proactive emotional health system, geared toward supporting emotional self-awareness and empathy, was built as a part of a long-term research plan for understanding the role digital technology can play in helping people to reflect on their beliefs, attitudes, and values. The system, G.I.R.L.S. (Girls Involved in Real-Life Sharing), allows users to reflect actively upon the emotions related to their situations through the construction of pictorial narratives. The system employs common-sense reasoning to infer affective content from the users' stories and support emotional reflection. Users of this new system were able to gain new knowledge and understanding about themselves and others through the exploration of authentic and personal experiences. Currently, the project is being turned into an online system for use by school counselors.