We examined the lived experiences of male undergraduates on the campus of a high-research-activity university in the northeastern United States. Interviews with 8 male undergraduates with a grade-point average lower than 2.0 revealed that their poor academic performances resulted from a combination of the following experiences: a disconnect between high school and university academic expectations, adherence to rigid male gender roles, an inability to set priorities and engage with faculty and staff, and the manifestation of mental health issues. We implemented the study as a front-end analysis to understand better these learners and their learning contexts. Recommendations for advising intervention are offered.