Student loans occupy a significant portion of the federal budget, as well as, the largest financial burden in terms of debt for graduates. This paper explores data-driven approaches towards understanding the repayment of such loans. Using statistical and machine learning models on the College Scorecard Data, this research focuses on extracting and identifying key factors affecting the repayment of a student loan. The specific factors can be used to develop models which provide predictive capability towards repayment rate, detect irregularities/non-repayment, and help understand the intricacies of student loans.