Despite the importance of romantic relationships for psychological health, there is limited research exploring how communication about relationships unfolds in families during adolescence and emerging adulthood (beyond the narrower topic of sex). As such, the current research explored the nature of caregiver-child communication about relationships and assessed whether this communication is associated with young people’s psychological health. We hypothesized that young people will have fewer and lower quality conversations about relationships in comparison to other developmental goals but that communication quality would improve with age. We also hypothesized that the quality of relationships communication would predict psychological health as indexed by self-esteem and psychological distress. In a series of two survey studies, adolescents (n = 129) and emerging adults (n = 716) reported on the frequency and quality of communication about relationships (and other developmentally-relevant topics including education, career, race/ethnicity) with their primary female caregiver and reported on their own psychological health. A subset of Study 1 participants additionally completed a daily diary assessing the frequency with which they discussed these topics and/or reported on their psychological health a second time. Results showed that conversations about relationships generally occurred less frequently than other topics and were also seen as the lowest in quality across assessments, though quality did improve with age. Moreover, even when controlling for communication about other topics, the frequency and quality of relationships communication positively predicted aspects of psychological health. Results indicate that young people may benefit from interventions designed to improve family communication about relationships.