Natural language understanding often depends on meanings that are implied rather than explicitly stated, requiring pragmatic reasoning. Despite strong performance on math and logical reasoning, large language models (LLMs) still trail humans on pragmatic inference, often defaulting to literal interpretations. To improve LLM pragmatic reasoning, we introduce PragReST, a self-supervised framework that constructs pragmatic QA data, generates counterfactual reasoning traces, and trains models to internalize them through supervised fine-tuning and reinforcement learning, without human-labeled training data or distillation from a stronger teacher. Across four pragmatic benchmarks (PRAGMEGA, LUDWIG, METOQA, and ALTPRAG) and multiple model families, including Qwen3, Gemma, and GPT-OSS, PragReST consistently improves over backbone models, task-specific pragmatic tuning baselines, and non-counterfactual variants of the same pipeline. On accuracy-based benchmarks, PragReST improves over the instruct backbone by 5.37% and 5.50% (absolute) for Qwen3-8B and Qwen3-14B, respectively. Our error analysis and ablations underscore the importance of counterfactual reasoning: PragReST primarily reduces errors caused by failures to contrast observed utterances with plausible alternatives, and removing counterfactual reasoning substantially reduces performance. Moreover, our training preserves out-of-domain performance on general-knowledge and mathematical reasoning benchmarks.

Meme captioning, the task of generating a sentence that describes the meaning of a meme, is both challenging and important in advancing Computational Meme Understanding (CMU). However, existing research has not explored its decomposition into subtasks or its connections to other CMU tasks. To address this gap, we introduce MemeInterpret, a meme corpus containing meme captions together with corresponding surface messages and relevant background knowledge. Strategically built upon the Facebook Hateful Memes dataset, MemeInterpret is the last piece in a set of corpora that unifies three major categories of CMU tasks for the first time. Extensive experiments on MemeInterpret and connected datasets suggest strong relationships between meme captioning, its two proposed subtasks, and the other two key categories of CMU tasks: classification and explanation. To stimulate further research on CMU, we make our dataset publicly available at https://github.com/npnkhoi/MemeInterpret.