This article suggests ways to teach teenagers about their right to complex personhood in relationships in a way that honours the psychological complexities of intimacy, as well as teenagers' wisdom as people already 'in' relationships. Recognition of students' complex personhood entails attention to two dimensions: (1) the emotional ambiguities, pleasures and risks inherent in all intimate relationships; and (2) the socio-structural context of students' lives. We draw from interviews with young adults about their teenage relationships, in which they challenge conventional understandings of 'healthy' versus 'unhealthy' relationship categories. These data reveal that teenagers may benefit from pedagogical conversations centred on the navigation of emotional risks versus the avoidance of risks. Interviews also illustrate how the larger social context and structural forces affecting teenagers' lives shaped the types of intimate harms they navigated, although they did not always have a language through which to understand this structural dimension. Throughout the article, we advance a complex personhood framework, calling on sex educators to centre the emotional ambiguities, depth, wisdom and social embeddedness of teenage relationships.