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This qualitative study examines a digital pen-pal project between preservice teachers (PTs) and fifth-grade students in exploring writing as relational, expressive, and transformative. Through asynchronous exchanges, participants composed across genres and identities, engaging in writing as a way to share their present and envision futures. Using frameworks of connected learning and writing as worldmaking, we analyzed letters, reflections, and assessments to trace pedagogical transformation. Findings highlight how feedback became culturally responsive, voice became a form of agency, and writing became a space for shared imaginative futures. This work offers a hopeful counter-narrative to standardization, rehumanizing teacher education and writing practices through creative, student-centered, and relational writing pedagogies.