Sexual selection is a major force shaping morphological and behavioral diversity. Existing theory focuses on courtship display traits such as morphological ornaments whose costs and benefits are assumed be to fixed across individuals' lifetimes. In contrast, empirically observed displays are often inherently dynamic, as vividly illustrated by the acrobatic dances, loud vocalizations, and vigorous motor displays involved in courtship behavior across a broad range of taxa. One empirically observed form of display flexibility occurs when signalers adjust their courtship investment based on the number of rival signalers. The predictions of established sexual selection theory cannot readily be extended to such displays because display expression varies between courtship events, such that any given display may not reliably reflect signaler quality. Thus, we lack an understanding of how dynamic displays coevolve with sexual preferences and how signalers should tactically adjust their display investment across multiple courtship opportunities. To address these questions, we extended an established model of the coevolution of a female sexual preference and a male display trait to allow for dynamic, flexible displays. We find that a dynamic display can coevolve with a sexual preference away from their naturally selected optima, though display intensity is a weaker signal of male quality than for static ornaments. Furthermore, we find that males evolve to decrease their display investment when displaying alongside more rivals. This research represents a first step towards generalizing the findings of sexual selection theory to account for the ubiquitous dynamism of animal courtship.