Because authenticity in education is a subjective judgment regarding the meaningfulness of an activity, a need exists to co-investigate with students classroom factors increasing authenticity of writing. In this case study, one 8th grade student's needs for authentic writing are explored in detail. Xavier's take on authentic writing illustrates how the factors of impact, choice, expression, and sharing connect in a unique way for this particular individual on specific writing tasks. Also, by examining in depth Xavier's individual perspective, one can see how Xavier's views align with and differ from previous research on authentic writing. Additionally, this article offers a conversation between the author and Xavier, depicting a method for structuring students' choices to increase authenticity. Additionally, the current study contributes to the extant literature by illustrating how authenticity depends on the values and life experiences students bring to the writing task, not the inherent value of the task itself.