This study examined the effect of previous romantic relationship involvement on later romantic relationship quality and tested whether adolescents' personality type (i.e., overcontrollers, undercontrollers, resilients) moderated this link. We answered our research questions in a sample of 320 Dutch participants (213 girls) who had a romantic relationship when they were 21 years old. At 12 years of age, their personality types were identified. At 21 years of age, participants reported their current romantic relationship quality (i.e., commitment, exploration, and reconsideration) and indicated the number of romantic relationships they had before. No main effects of the number of romantic relationships on current romantic relationship quality were found. There were significant interaction effects between personality types and the number of romantic relationships on romantic relationship quality. With more romantic relationship experiences, undercontrollers committed less to and explored less in their current romantic relationship. No such link was found for resilients and overcontrollers.