<i>Mentorship in higher education is widely acknowledged for its positive impact on students. Many institutions have implemented one-on-one guidance systems, such as faculty advising programs and faculty/peer mentorship initiatives. Yet, there remains a gap in understanding how students perceive mentoring, particularly during the transitional period before and early in their time in college. In light of the increasing focus on emerging adulthood within the field of developmental psychology, understanding students’ academic development during their transitioning years, particularly the role of mentorship becomes increasingly essential. This qualitative study employs positioning analysis to explore students’ evolving sense-making of mentoring relationships during two distinct phases: the final year of high school and the first year of college. This research conducts a comparative analysis to investigate how two students’ perceptions of mentorship change during their transition into college and differ from one another. The study aims to illuminate students’ sense-making of mentors and mentorship experiences throughout their high school and college transition and explores the unique ways students discuss mentorship as they transition. The findings unveil the contrasting experiences and evolving roles of mentors of each participant through the lens of their lived experiences, providing an insight into students’ individual developing conceptions of mentors and mentorship experience. This study offers a nuanced understanding of first-year college students’ sense-making activities as they navigate the complexities and academic demands of college. The insights gained from this study not only illuminate how qualitative methods provide yet-to-be-understood processes but also can further contribute to designing mentorship programs in higher education settings tailored to meet students’ needs from the moment they step onto campus. As the research landscape continues to evolve, qualitative studies like this contribute to the ever-advancing knowledge and practice of mentorship in higher education, supporting the diverse developmental needs of today’s college students.</i>
