This paper theorizes about how relational uncertainty may predict features of date request messages within courtship. It reports a study in which 248 individuals role-played leaving a date request voice mail message for their partner. Relational uncertainty was negatively associated with the fluency (H1), affiliativeness (H2), relationship focus (H3), explicitness (H4), and perceived effectiveness (H5) of messages. Also as expected, relational uncertainty was negatively associated with people's perceptions of the effectiveness of their messages after covarying the judgments of independent observers (H6). Relational uncertainty continued to predict features of messages when length of romantic interest was covaried (RQ1). The paper concludes by discussing the implications of the results for understanding the link between relational uncertainty and message production.