The focus of this article is a nine-month long practice-led research (PLR) project. As part of this project, the author developed a cross-curricular program as part of a middle-school humanities course in order to facilitate student discussion. The program, which the students and author dubbed "BlogArt," began as a writing- and literature-based program but evolved into an art- and blog-based exploration of potentially divisive issues. Taking the discussions to the blogosphere encouraged students to creatively close the space between thought and communication, which is fundamental to meaningful art. The process followed in BlogArt holds potential operational significance for teachers at the secondary level. In this article, the author will explore the following questions: (1) How does one student's comfort with expression through symbolic representations evolve through an academic year of online sharing?; (2) How can blogs and art be used in combination to explore sensitive topics and develop conflict resolution skills?; and (3) How can a combination of art, technology, critical reading, and writing be presented to promote authentic communication with the world outside of the classroom?