In this article, the authors report on usage of 21st-century technology, and a collaborative project that allowed middle school art students and preservice teachers to share their artwork and receive feedback in a constructivist learning environment. Middle school students often deal with issues such as bullying, divorce, and depression; they can also be as silly as they are serious about their own occasional awkwardness in adolescence. In a constructivist teaching and learning environment, they can address adolescent concerns in their artwork. Students collaborated to gain a deeper knowledge and understanding of their art ideas, while the art teachers served as facilitators to their students: guides, assistants, and reviewers. They encouraged students to research big ideas and artists, and to discover materials and processes that might deepen their knowledge and develop more complex, refined solutions to their art problems. In a technological environment, students can access information from content experts and contemporary artists, and collaborate across distance and in real time; art educators can give and get feedback from differing teaching and learning levels.