Literature offers readers lessons that transcend beyond its pages. Through these lessons, through thematic topics, and through characters’ interactions and conflicts, there are opportunities for students to notice and develop connections to our dynamic everyday lives. Join me as I share a unit that fosters student creativity at the intersection of literature, media literacy, and technology: Dear Evan Hansen through the lens of Critical Media Literacy. In this session, participants will learn how I, an ELA teacher, paired with my district’s EdTech team to design a unit focused on teaching students more than the literacy processes of reading and writing. Participants will learn how, through our partnership, we connected the trials and tribulations the characters in the play faced, with tangible strategies for how students could, and should behave and interact with peers, friends, and their communities online. We developed strategies to incorporate meaningful utilization of AI in the classroom, including an opportunity for students to interact with the plays’ characters through a character chatbot, an activity that lifted conflicts and characters off the pages of the play. Additionally, participants will walk away with strategies for teaching Critical Media Literacy, not in isolation, but connected directly to the curriculum to foster analytical thinking.