To address an important gap in creating children's stories for vocabulary enrichment, we investigate the automatic evaluation of how well stories convey the semantics of target vocabulary words, a task with substantial implications for generating educational content. We motivate this task, which we call measuring contextual informativeness in children's stories, and provide a formal task definition as well as a dataset for the task. We further propose a method for automating the task using a large language model (LLM). Our experiments show that our approach reaches a Spearman correlation of 0.4983 with human judgments of informativeness, while the strongest baseline only obtains a correlation of 0.3534. An additional analysis shows that the LLM-based approach is able to generalize to measuring contextual informativeness in adult-directed text, on which it also outperforms all baselines.

Both humans and machines learn the meaning of unknown words through contextual information in a sentence, but not all contexts are equally helpful for learning. We introduce an effective method for capturing the level of contextual informativeness with respect to a given target word. Our study makes three main contributions. First, we develop models for estimating contextual informativeness, focusing on the instructional aspect of sentences. Our attention-based approach using pre-trained embeddings demonstrates state-of-the-art performance on our single-context dataset and an existing multi-sentence context dataset. Second, we show how our model identifies key contextual elements in a sentence that are likely to contribute most to a reader's understanding of the target word. Third, we examine how our contextual informativeness model, originally developed for vocabulary learning applications for students, can be used for developing better training curricula for word embedding models in batch learning and few-shot machine learning settings. We believe our results open new possibilities for applications that support language learning for both human and machine learners.