This study explored three purposefully-sampled avid adolescent male writers' experiences at a residential summer writing workshop program. It investigated how the social context of the program influenced the writing of the focal students, the ways that they identified themselves as writers, and the risks that they took in their works. It also examined if the participants' experiences at the program were influenced by their gender. The study used a cross-case analysis to explore in-common and unique themes in the students' experiences. The findings address three themes: community, risk-taking, and the perceived influence of gender, indicating the participants experienced these themes in ways that were common in some ways, but also distinct based on the participants' individual characteristics and the aspects of the Workshop each identified as most significant.