What Makes a Question Curious? Measuring Model Curiosity in Human-LLM Interactions

Large Language Models (LLMs) provide a new opportunity to study how language shapes exploratory cognition because conversational strategies can be systematically manipulated at inference time. We introduce CURIOBOT, a framework that operationalizes Berlyne's collative variables, novelty, complexity, conflict, and uncertainty, as adaptive linguistic interventions for conversational tutoring. Across 270 tutoring conversations spanning multiple model families, domains, and topic complexity levels, curiosity-oriented interventions consistently increased exploratory learner behaviors, producing up to 2.4x more conversational turns under fixed time budgets. To measure these effects, we further introduce a learner-centered evaluation framework capturing exploratory questioning, conversational agency, productive struggle, and observable curiosity. Learner-side gains persisted even when tutor-side instructional quality remained unchanged, suggesting that curiosity functions as a partially independent interaction-level mechanism. More broadly, our results demonstrate that LLM-mediated dialogue can serve as a scalable experimental framework for studying how language shapes exploratory learning behavior.

User queries are often underspecified and may admit multiple valid interpretations. Rather than silently making assumptions about the user's intent, a helpful assistant should surface such ambiguity by asking a clarifying question. Doing so requires two abilities: recognizing that a query is ambiguous, and acting on that recognition by seeking clarification instead of answering directly. To study these abilities, we evaluate models on ambiguous, unambiguous, and disambiguated questions in three settings: standard question answering, explicit ambiguity judgment, and behavioral analysis, where a judge model classifies responses as direct answers, refusals, or clarifying questions. We find a clear gap between recognition and behavior: models often identify ambiguity when explicitly asked to judge it, yet in the QA setting they overwhelmingly default to direct answers. Retrieved context further widens this gap by improving answerability while making models even less likely to ask clarifying questions.

Standard LLM benchmarks evaluate the assistant turn: the model generates a response to an input, a verifier scores correctness, and the analysis ends. This paradigm leaves unmeasured whether the LLM encodes any awareness of what follows the assistant response. We propose user-turn generation as a probe of this gap: given a conversation context of user query and assistant response, we let a model generate under the user role. If the model's weights encode interaction awareness, the generated user turn will be a grounded follow-up that reacts to the preceding context. Through experiments across $11$ open-weight LLMs (Qwen3.5, gpt-oss, GLM) and $5$ datasets (math reasoning, instruction following, conversation), we show that interaction awareness is decoupled from task accuracy. In particular, within the Qwen3.5 family, GSM8K accuracy scales from $41\%$ ($0.8$B) to $96.8\%$ ($397$B-A$17$B), yet genuine follow-up rates under deterministic generation remain near zero. In contrast, higher temperature sampling reveals interaction awareness is latent with follow up rates reaching $22\%$. Controlled perturbations validate that the proposed probe measures a real property of the model, and collaboration-oriented post-training on Qwen3.5-2B demonstrates an increase in follow-up rates. Our results show that user-turn generation captures a dimension of LLM behavior, interaction awareness, that is unexplored and invisible with current assistant-only benchmarks.