The challenge colleges and universities encounter in the United States is retention of freshmen male college students. The National Center for Education Statistics (2012) reported that 37% of freshman males enrolled in a postsecondary institution in 2003-04 dropped out by June 2009. Unfortunately, 17% dropped-out within the first-year without completing a degree or certificate program (Ross, Kena, Rathbun, Kewal, Zhang, Kristapovich, and Manning, 2012). This qualitative case study explored the opinions and perceptions of freshman, sophomore, and non-returning freshman male students to understand factors that challenged and supported the transition into the college environment. The study used interviews to collect, analyze, and describe the data from 16 semi-structured interviews conducted at a large public four-year research institution. Participants consisted of six freshmen, six sophomores, and four non-returning freshmen student population. Three major factors were identified: social engagement, study skills-behavior and instructor-student relationships. The results provided insight into how educational leaders can create a balanced social and academic first-year experience for freshman male students.