Hirschi argued that delinquent youth tend to form relatively "cold and brittle" relationships with peers, depicting these youths as deficient in their attachments to others. The current analysis explores connections between delinquency and the character of adolescent romantic ties, drawing primarily on the first wave of the Toledo Adolescent Relationships Study, and focusing on 957 teens with dating experience. We examine multiple relationship qualities/dynamics in order to explore both the "cold" and "brittle" dimensions of Hirschi's hypothesis. Regarding the "cold" assumption, results suggest that delinquency is not related to perceived importance of the romantic relationship, level of intimate self-disclosure or feelings of romantic love, and more delinquent youth actually report more frequent contact with their romantic partners. Analyses focused on two dimensions tapping the "brittle" description indicate that while durations of a focal relationship do not differ according to level of respondent delinquency, more delinquent youths report higher levels of verbal conflict.