The difficult relationship between boys and writing is well documented; its causes and solutions are the source of passionate debate. Of the many trends the author has observed in 20 years as a classroom teacher, one of the most disheartening has been a deteriorating interest in writing among male students. Their disengagement manifests in many ways, from quiet malaise to blunt verbalization. Despite the author's focus, over the last decade, on "process" rather than "product" in writing, the majority of boys taught continued to show a lack of enthusiasm. Writers' workshop models that focused on developing "seed moments" through personal narratives did little to spark their interest. The author prodded them to write descriptive, clearly organized essays, but they showed little commitment. As a result, he saw well-organized writing that was fairly impressive, but behind it was an absence of passion and a growing disdain for the subject. To explore the problem further, the author joined the Afterschool Matters Practitioner Research Fellowship program in Seattle through School's Out Washington, a local nonprofit advocacy group for out-of-school time instruction. Supported by the National Institute on Out-of-School Time and the National Writing Project, the fellowship brought teachers like together with afterschool practitioners. Inspired by this collaboration, the author began to see new solutions to the problem of dwindling engagement among male writers. He began to realize that the school-time context of writing instruction contributed to the problem. The pressures on students and teachers to meet deadlines, reach achievement goals, and address standards encouraged more compliance than creativity. What if students could write in a more liberated context--where grades, products, and achievement goals were no longer factors? These questions led the author to develop Write After School, an afterschool writing program. Write After School offers choice within structure and encourages interaction in ways designed to engage reluctant male writers. Kids choose their own topics, receive feedback, and have chances to share and talk about their work. The struggles boys face with writing and the afterschool writing program are described in this article.