Traditional automated metrics for evaluating conditional natural language generation use pairwise comparisons between a single generated text and the best-matching gold-standard ground truth text. When multiple ground truths are available, scores are aggregated using an average or max operation across references. While this approach works well when diversity in the ground truth data (i.e. dispersion of the distribution of conditional texts) can be ascribed to noise, such as in automated speech recognition, it does not allow for robust evaluation in the case where diversity in the ground truths represents signal for the model. In this work we argue that existing metrics are not appropriate for domains such as visual description or summarization where ground truths are semantically diverse, and where the diversity in those captions captures useful additional information about the context. We propose a novel paradigm for multi-candidate evaluation of conditional language generation models, and a new family of metrics that compare the distributions of reference and model-generated caption sets using small sample sets of each. We demonstrate the utility of our approach with a case study in visual description: where we show that existing models optimize for single-description quality over diversity, and gain some insights into how sampling methods and temperature impact description quality and diversity.