Understanding interpersonal relationships and the skills an individual needs for building and engaging in interpersonal relationships is central to the study of the construct of connection, as an indicator of positive youth development, and to understanding the challenges adolescents face as they transition to adulthood. Accordingly, we conducted a thematic analysis of the reflections about relationships provided by young men beginning postsecondary education. We attended to what they said made these relationships meaningful or important to them, the actions and processes described as part of these relationships, and the role of these relationships in their life plans. Themes identified included indicating closeness through metaphor and hyperbole, connection as feeling close and cared for, emotional expression, talking and listening, putting effort into a relationship, acknowledging difficulty, and improving relationships. We discuss implications of our findings for future research with adolescents and young adults in relation to masculinity ideologies and positive youth development approaches.