This qualitative study provides a framework for planning institutional change and considering present institutional practices by examining the challenges and rewards experienced by first-year students in regard to adapting to the academic and social culture of a large commuter university. The transition from compulsory public education to optional post-secondary education is recognized as a pivotal point in student success at university. While there has been much research on the undergraduate experience, there have been few studies exploring the specific transition experiences of frosh students. The purpose of this research is to understand the educational experiences that shape transitions, sense of institutional fit, and educational goals of first-year undergraduate students at a large university in Western Canada. The influence of gender in each of these areas is explored. This research builds upon previous research about student transitions and addresses general concerns about the quality of educational experiences at Canadian universities. It could be used to inform policy development with regard to student academic growth, career counselling, and student retention. This research is specific to a General Study Faculty at a large commuter university and resultant generalizations may vary in applicability for other undergraduate programs.