PurposeAssertive communication has been associated with higher levels of condom use among youth using self-report survey methodology. The purpose of this study was to examine the subjective ratings of assertiveness among young, romantically involved couples in the context of a condom negotiation task. MethodsUsing an innovative video-recall procedure, 32 couples (64 youth) engaged in a videotaped condom negotiation task and then rated self and partners' level of assertiveness. Both individual ratings of assertiveness and couple-level assertiveness were assessed using dyadic hierarchical linear modeling. ResultsIndividuals' assertiveness was positively associated with condom use. Unexpectedly, the overall level of assertiveness in couples showed a curvilinear association with condom use. Very high and very low assertiveness was associated with lower condom use, whereas moderate levels of assertiveness were associated with higher condom use. ConclusionsModerate levels of assertiveness during condom negotiation may facilitate condom use in young couples. Increasing condom use among romantic partners may require developing interventions that strengthen youths' ability to engage in assertive communication strategies that balance emotional intimacy with self-advocacy.