Conditional Semantic Textual Similarity (C-STS) measures the semantic proximity between text segments under a specific condition, thereby overcoming the ambiguity inherent in traditional STS. However, existing methods are largely confined to discriminative models, failing to fully integrate recent breakthroughs in the NLP community concerning Large Language Models (LLMs) and Reinforcement Learning (RL). RL is a particularly well-suited paradigm for this task, as it can directly optimize the non-differentiable Spearman ranking metric and guide the reasoning process required by C-STS. However, we find that naively applying listwise RL fails to produce meaningful improvements, as the model is overwhelmed by complex, coarse-grained reward signals. To address this challenge, we introduce PoLi-RL, a novel Point-to-List Reinforcement Learning framework. PoLi-RL employs a two-stage curriculum: it first trains the model with simple pointwise rewards to establish fundamental scoring capabilities, then transitions to a hybrid reward that combines pointwise, pairwise, and listwise objectives to refine the model's ability to discern subtle semantic distinctions. Crucially, we propose an innovative Parallel Slice Ranking Reward (PSRR) mechanism that computes ranking rewards in parallel slices, where each slice comprises same-indexed completions from different samples. This provides a precise, differentiated learning signal for each individual completion, enabling granular credit assignment and effective optimization. On the official C-STS benchmark, PoLi-RL achieves a Spearman correlation coefficient of 48.18, establishing a new SOTA for the cross-encoder architecture. As the first work to successfully apply RL to C-STS, our study introduces a powerful and precise paradigm for training LLMs on complex, ranking-based conditional judgment tasks.

The meaning conveyed by a sentence often depends on the context in which it appears. Despite the progress of sentence embedding methods, it remains unclear how to best modify a sentence embedding conditioned on its context. To address this problem, we propose Condition-Aware Sentence Embeddings (CASE), an efficient and accurate method to create an embedding for a sentence under a given condition. First, CASE creates an embedding for the condition using a Large Language Model (LLM), where the sentence influences the attention scores computed for the tokens in the condition during pooling. Next, a supervised nonlinear projection is learned to reduce the dimensionality of the LLM-based text embeddings. We show that CASE significantly outperforms previously proposed Conditional Semantic Textual Similarity (C-STS) methods on an existing standard benchmark dataset. We find that subtracting the condition embedding consistently improves the C-STS performance of LLM-based text embeddings. Moreover, we propose a supervised dimensionality reduction method that not only reduces the dimensionality of LLM-based embeddings but also significantly improves their performance.

Semantic textual similarity (STS), a cornerstone task in NLP, measures the degree of similarity between a pair of sentences, and has broad application in fields such as information retrieval and natural language understanding. However, sentence similarity can be inherently ambiguous, depending on the specific aspect of interest. We resolve this ambiguity by proposing a novel task called Conditional STS (C-STS) which measures sentences' similarity conditioned on an feature described in natural language (hereon, condition). As an example, the similarity between the sentences "The NBA player shoots a three-pointer." and "A man throws a tennis ball into the air to serve." is higher for the condition "The motion of the ball" (both upward) and lower for "The size of the ball" (one large and one small). C-STS's advantages are two-fold: (1) it reduces the subjectivity and ambiguity of STS and (2) enables fine-grained language model evaluation through diverse natural language conditions. We put several state-of-the-art models to the test, and even those performing well on STS (e.g. SimCSE, Flan-T5, and GPT-4) find C-STS challenging; all with Spearman correlation scores below 50. To encourage a more comprehensive evaluation of semantic similarity and natural language understanding, we make nearly 19K C-STS examples and code available for others to train and test their models.