Young Black and Latino men transition from high school to 4-year universities at rates considerably lower than their peers. College-going disparities by gender are partly influenced by young men's constrained access to social capital in high school. This research explores how gendered inequalities in social capital arise for college-aspiring seniors at an urban high school. The data suggest that young men were more reluctant than their young women to "ask for directions" on their way to college because they were concerned about being perceived as bothersome, and they believed their social disadvantages were insignificant. Young men who were in contexts that allowed them to overcome these challenges successfully collected important college-going social capital. These findings can support researchers and practitioners who seek to expand college access in marginalized communities.