Various dimensions of parenting have been associated with youth risk behaviors, such as substance use and dating violence. These associations have spawned many prevention strategies that focus on parenting. However, it is unclear which characteristics of parent–youth relationships, and thus, which parent-focused prevention strategies, may be most influential in youth risk behaviors and, thus, which should be targeted in prevention. Using responses from the YouthStyles 2007 survey (N = 1,357), this study identified three youth-reported parent–youth relationship characteristics: communication about risk behaviors, closeness/respect, and rules/monitoring. The authors examined the associations among these characteristics and youths’ demographics, attitudes supporting controlling dating relationships, and use of alcohol, marijuana, and tobacco. Results suggested risk behavior communication was more frequently reported by girls and was more frequent among older youth. Closeness/respect and rules/monitoring were more frequent among younger youth. Regressions suggested communication about risk behaviors was not a predictor of attitudes supporting controlling dating relationships but was a significant predictor of substance use, closeness/respect and rules/monitoring predicted substance nonuse and attitudes unsupportive of controlling dating relationships. The findings suggest that parental communication alone may not be sufficient to influence youth risk taking, but that parental monitoring and the establishment of respectful, close relationships with children may be important elements of parent-focused health promotion efforts.