Through the analysis of alumni survey data from three graduating cohorts, this study examined the relationships between ideological interaction, college outcomes, and career achievements and explored factors that helped to promote interaction across ideological boundaries on college campuses. Its findings show that compared with less interactive students, students who engaged substantially in ideological interaction during college indicated higher levels of skill development, reported higher career success and life satisfaction, and were more likely to assume leadership roles in civic activities. Implications for future research and institutional efforts to foster ideological interaction are discussed.