The college transition involves social challenges for students, including concerns about distance from family and hometown friends, and pressure to build a new social network on campus. Students who are successfully navigating these social challenges should be better adjusted on campus and feel more satisfied with the direction of their lives. We measured two expressions of relatedness in incoming, central US students’ ( N = 244; M age = 18.1 years; 78.6% women) autobiographical recollections of the college transition: (a) dispositional relatedness (DR) and tendencies to emphasize motivations for connecting with others; and (b) situational relatedness (SR) and reflections on successes and challenges within specific relationship domains. We hypothesized that both expressions of relatedness would be positively and distinctly associated with longitudinal reports of college adjustment (i.e., belonging) and subjective well-being (i.e., life satisfaction). We also hypothesized that changes in college adjustment would mediate associations between expressions of relatedness and well-being. Findings broadly supported expectations. Each expression of relatedness robustly predicted better student outcomes longitudinally. Further, improvements in college belonging and decreases in homesickness mediated the ties between situational relatedness and subjective well-being. We discuss the implications of these findings for the college transition and student support services.