Through surveying a Princeton pilot mentoring program and interviewing current Princeton students and alumni, this thesis examines the interplay between the undergraduate experience and alumni mentorship at Princeton University. While current and recent undergraduates express a strong and widespread desire to receive alumni mentorship, I find that Princeton’s current mentorship programs are inadequate to address students’ ever evolving needs. Thus, this thesis argues that Princeton University, and other institutions, should implement structured and comprehensive mentorship initiatives designed to foster meaningful and sustained relationships. Ultimately, my results suggest that if universities establish a robust alumni mentorship program, they will cultivate a more inclusive campus environment, strengthen alumni engagement with their alma mater, and enhance the trajectory of their students’ lives.