Three studies examined the effects of dispositional attachment orientations and contextual priming of attachment security on the willingness to drive recklessly. In all three, adolescents were exposed to primes of attachment security (a poster in Study 1, a video in Study 2, a guided imagination task in Study 3), positive affect, or neutral affect, and were then asked to report their willingness to drive recklessly. Participants were also asked to report on their attachment orientations (anxiety, avoidance), self-esteem, and self-relevance of driving. Attachment anxiety was related to higher willingness to drive recklessly. In addition, as compared to positive affect and neutral priming, attachment security priming exacerbated highly anxiously attached participants' tendency to drive recklessly, but reduced this tendency among participants scoring low on attachment anxiety. Importantly, these effects could not be explained by variables unrelated to attachment. The discussion emphasizes the relevance of attachment theory for understanding risk-taking behavior, and relates to practical implications of the studies.