Many educators believe that the path to a better future is a college education. Initiatives that promote college-going cultures are quite commonplace in many public high schools with some offering elective college-prep support programs like Advancement Via Individual Determination (AVID). Yet, certain groups of students are not taking advantage of these opportunities. In the initial AVID sections at a metropolitan high school in the American Southwest, the girls out-numbered the boys 2:1, and the Hispanic girls outnumbered the Hispanic boys by almost 3:1. The purpose of this study was to uncover some of the factors that influenced five Hispanic males' participation, or lack thereof, in AVID, and the ways in which those factors connected to their masculine identities. What the participants say about what influenced them to be involved, or not, in the program is reported. Some themes revealed in the interviews include how the participants' scholar identity is connected to their masculine identity, how they balance their "coolness" quotient with their desires to achieve academic success, how they depend on personal relationships and collaboration, and how their families and communities have influenced them. This information may lead to the development of strategies that will increase future representation of Hispanic males in similar programs.