College student retention has been described as a puzzle because retention rates have stagnated, and in some cases declined, despite over seventy years of research into the problem. The magnitude of the problem is that 50 percent of college students will leave their institution before obtaining a degree (Braxton, Hirschy, & McClendon, 2011). In an effort to improve retention rates, colleges and universities have concentrated their attention on first year students. But this concentrated strategy may have simply transferred the retention problem into the second year where retention rates for many schools are as low as first year rates (Amaury, Barlow, & Crisp, 2005). While advising practices have been identified as one of the three top contributors to increasing retention, major gaps exist about the role academic advising might play in the retention of second year students. The present correlational study was undertaken to fill gaps in the mostly conceptual second year literature base which implies second year students differ from first year and upper division students. Advising formed the focus of the study because advising has been identified as one of the most important methods for putting students into a mentoring relationship with college staff and faculty, a practice with strong ties to retention (Habley & McClanahan, 2004; Kuh, 2008). Six research questions were posed in the study which asked whether second year students differed from first year and upper division students and whether retained second year students differed from not retained second year students in their attitudes toward and experiences with advising. Using simultaneous and logistic regression models, and controlling for confounding variables, statistically significant differences were found between second year students and their first year and upper division peers as well as between retained second year students and not retained second year students. The findings of difference between second year and other students provide the growing second year retention literature with an empirical basis to support previously held assumptions about difference between class years which had also formed the basis for presumptions about practice for second year success and retention. Many of the findings in this study also support present retention and second year research and prescriptions for practice provided by that research.