This study examined the interrelations between parental relationships, romantic relationships, and antisocial behavior among female and male juvenile delinquents. Participants from a diverse sample of 1,354 adolescents (14–17 years) adjudicated of a serious (i.e. felony) offense were matched based on age, race, and committing offense, yielding a sample of 184 girls matched with 170 boys. Results indicate that while female offenders are more likely to date boys 2 years their senior, age difference alone is not directly related to self-reported offending. Instead, findings suggest that girls who engage in self-reported delinquent behavior are more likely to experience a high degree of antisocial encouragement exerted on them by their current romantic partner. Interestingly, this relation varies with the quality (warmth) of parental relationships and the romantic partner's level of antisocial encouragement, with the association between partner encouragement and self-reported offending being strongest among youths reporting warm relationships with their opposite-sex parent.