Traditional automated metrics for evaluating conditional natural language generation rely on pairwise comparisons between a single generated text and the best-matching gold-standard reference. This method is effective when ground truth data diversity can be attributed to noise, however, it falls short when diversity in references holds valuable contextual information, as in visual description or summarization, as it does not evaluate the ability of a model to generate text matching the diversity of the ground truth samples. In this paper, we challenge the adequacy of existing metrics in such semantically diverse contexts and introduce a novel approach for evaluating conditional language generation models, leveraging a family of meta-metrics that build on existing pairwise distance functions. These meta-metrics assess not just single-samples, but distributions of reference and model-generated captions using small sample sets. We demonstrate our approach through a case study of visual description in the English language which reveals not only how current models prioritize single-description quality over diversity, but further sheds light on the impact of sampling methods and temperature settings on description quality and diversity.