We characterize how people are turning to LLMs as oracles: all-knowing authorities on subjective personal questions. Motivated by risks to users' autonomy and well-being, we develop a typology and LLM-based methods to measure this form of AI reliance at scale and understand how people are offloading judgment and decision-making to AI. Applying our typology to public usage data (68K prompts from WildChat and ThoughtTrace), we find that LLM-as-oracle use has increased over time (2023-2026) and is more prevalent among younger users. We further build a privacy-preserving data donation tool to analyze individuals' longitudinal usage data (140K prompts from 52 participants), identifying similar trends. People are often unaware of their own LLM-as-oracle use, and express dissatisfaction with this behavior after seeing our tool's analysis. Finally, we identify two drivers of LLM-as-oracle use: people's perceptions of AI and the behavior of AI models themselves, which motivate possible interventions to support users' self-deliberation.
Large language models (LLMs) are increasingly used to simulate human behavior, but their ability to simulate individual privacy decisions is not well understood. In this paper, we address the problem of evaluating whether a core set of user persona attributes can drive LLMs to simulate individual-level privacy behavior. We introduce PrivacySIM, an evaluation suite that benchmarks LLM simulation of user privacy behavior against the ground-truth responses of 1,000 users. These users are drawn from five published user studies on privacy spanning LLM healthcare consultations, conversational agents, and chatbots. Drawing on these user studies, we hypothesize three persona facets as plausible predictors of privacy decision-making: demographics, previous experiences, and stated privacy attitudes. We condition nine frontier LLMs on subsets of these three facets and measure how often each model's response to a data-sharing scenario matches the user's actual response. Our findings show that (1) privacy persona conditioning consistently improves simulation quality over no-persona conditioning, but even the strongest model (40.4% accuracy) remains far from faithfully simulating individual privacy decisions. (2) A user's stated privacy attitudes alone may not be the best predictor because they often diverge from the user's actual privacy behavior. (3) Users with high AI/chatbot experience but low stated privacy attitudes are the most challenging to simulate. PrivacySIM is a first step toward understanding and improving the capabilities of LLMs to simulate user privacy decisions. We release PrivacySIM to enable further evaluation of LLM privacy simulation.
We examine whether human psychometric questionnaires can serve as reliable tools for characterizing and predicting LLM behavior in everyday user interactions. We analyze eight open-source LLMs by comparing their value and personality profiles derived from two different methods: Likert self-reports on established questionnaires (PVQ-40/21 and BFI-44/10) and generation probabilities over value-laden responses to everyday user queries. The two profiles diverge substantially. Within-construct item consistency, often cited as evidence of stable LLM dispositions, disappears in generation probabilities. We find that established questionnaire items contain explicit lexical cues that allow models to recognize the target construct and respond in alignment-consistent, socially desirable ways, whereas realistic user queries contain far less recognizable cues. In addition, demographic persona prompts shift models' responses to human questionnaires in ways consistent with real human patterns, but no such shifts appear in the generation setting, highlighting that human questionnaires overestimate LLMs' ability to faithfully reproduce expected psychological traits when role-playing demographic personas. Overall, our study indicates that questionnaire scores alone should not be treated as evidence of LLMs' response tendencies in realistic user interactions, and supports generation-probability profiling with ecologically valid items as a complementary behavioral measure.
Tool-use LLMs are increasingly asked to act on users' behalf, but existing benchmarks usually focus on profile recall, style imitation, generic tool use, or response-level personalization. We introduce UserToolBench , a benchmark for personalized decision making in tool-use LLMs. UserToolBench tests whether a model can infer latent user preferences from interaction history, recognize when clarification is needed, and produce user-aligned tool-call trajectories under incomplete information. The benchmark is built from privacy-sanitized real interaction traces and combines structured persona profiles, public API-style tool ecosystems, and long-horizon multi-turn trajectories. It includes 10 user profiles, 36 tool sets, 1,065 turns, 170 unique tools, and evaluation-focused task types covering lack-of-information, single-tool, and multi-tool settings. Experiments with strong tool-use LLMs show that current models still have difficulty with personalized delegation. Multi-tool coordination, missing-constraint inference, and long-horizon behavioral consistency remain major bottlenecks. These results suggest that personalization evaluation should move beyond asking whether outputs sound user-specific and instead ask whether LLMs make correct decisions for the users they represent.