This article is a cross-section of stories of three young men navigating the expectations of a school with a 100% college admissions goal. Similar to their classmates, none of these male teens had a parent who had attended college. In addition, each of them had at one point in their high school lives declared that they would be dropping out of high school. Their stories bring to light privileged assumptions and hidden struggles about what it takes for seniors in a low-income district to be college-bound and, in doing so, prove themselves worthy of public recognition.