Large Language Models (LLMs) can provide accurate word definitions and explanations for any context. However, the scope of the definition changes for different target groups, like children or language learners. This is especially relevant for homonyms—words with multiple meanings—where oversimplification might risk information loss by omitting key senses, potentially misleading users who trust LLM outputs. We investigate how simplification impacts homonym definition quality across three target groups: Normal, Simple, and ELI5. Using two novel evaluation datasets spanning multiple languages, we test DeepSeek v3, Llama 4 Maverick, Qwen3-30B A3B, GPT-4o mini, and Llama 3.1 8B via LLM-as-Judge and human annotations. Our results show that simplification drastically degrades definition completeness by neglecting polysemy, increasing the risk of misunderstanding. Fine-tuning Llama 3.1 8B with Direct Preference Optimization substantially improves homonym response quality across all prompt types. These findings highlight the need to balance simplicity and completeness in educational NLP to ensure reliable, context-aware definitions for all learners.

Ambiguous words or underspecified references require interlocutors to resolve them, often by relying on shared context and commonsense knowledge. Therefore, we systematically investigate whether Large Language Models (LLMs) can leverage commonsense to resolve referential ambiguity in multi-turn conversations and analyze their behavior when ambiguity persists. Further, we study how requests for simplified language affect this capacity. Using a novel multilingual evaluation dataset, we test DeepSeek v3, GPT-4o, Qwen3-32B, GPT-4o-mini, and Llama-3.1-8B via LLM-as-Judge and human annotations. Our findings indicate that current LLMs struggle to resolve ambiguity effectively: they tend to commit to a single interpretation or cover all possible references, rather than hedging or seeking clarification. This limitation becomes more pronounced under simplification prompts, which drastically reduce the use of commonsense reasoning and diverse response strategies. Fine-tuning Llama-3.1-8B with Direct Preference Optimization substantially improves ambiguity resolution across all request types. These results underscore the need for advanced fine-tuning to improve LLMs’ handling of ambiguity and to ensure robust performance across diverse communication styles.