The relationship between reported bullying, reported dating violence, and dating relationship quality measured through couple observations was examined. Given past research demonstrating similarity between peer and dating contexts, we expected that bullying would predict negative dating experiences. Participants with dating experience (n = 585; 238 males, M _age = 15.06) completed self-report assessments of bullying and dating violence perpetration and victimization. One month later, 44 opposite-sex dyads (M _age = 15.19) participated in behavioral observations. In 10-min sessions, couples were asked to rank and discuss areas of relationship conflict while being video-recorded. Qualities of the relationship were later coded by trained observers. Regression analysis revealed that bullying positively predicted dating violence perpetration and victimization. Self-reported bullying also predicted observations of lower relationship support and higher withdrawal. Age and gender interactions further qualified these findings. The bullying of boys, but not girls, was significantly related to dating violence perpetration. Age interactions showed that bullying was positively predictive of dating violence perpetration and victimization for older, but not younger adolescents. Positive affect was also negatively predicted by bullying, but only for girls. These findings add to the growing body of evidence that adolescents carry forward strategies learned in the peer context to their dating relationships.