As conversational companions, large language models (LLMs) often have access to users’ emotional states. We study how this *affective context* modulates LLM sycophancy in subjective, evaluative interactions, where users share actions or opinions that invite feedback. Drawing on ingratiation theory, we measure sycophancy as the divergence between a model’s independent evaluation and its user-facing response, elicited by presenting the same content as either a third-party account or the user’s own disclosure. Across seven LLMs and two Reddit datasets (r/AmItheAsshole and r/TrueUnpopularOpinion), we find that this divergence is systematic and strongly one-directional. User-facing responses consistently soften or withhold negative or oppositional judgments. Affective context further amplifies this divergence with negative states, particularly loneliness and distress, producing the largest effects. These findings suggest that affective context functions as a vulnerability signal that suppresses critical feedback when users may need it most, often through *evasive sycophancy*, in which models retreat toward non-committal responses rather than outright agreement.

Natural Language Processing tasks that aim to infer an author’s private states, e.g., emotions and opinions, from their written text, typically rely on datasets annotated by third-party annotators. However, the assumption that third-party annotators can accurately capture authors’ private states remains largely unexamined. In this study, we present human subjects experiments on emotion recognition tasks that directly compare third-party annotations with first-party (author-provided) emotion labels. Our findings reveal significant limitations in third-party annotations—whether provided by human annotators or large language models (LLMs)—in faithfully representing authors’ private states. However, LLMs outperform human annotators nearly across the board. We further explore methods to improve third-party annotation quality. We find that demographic similarity between first-party authors and third-party human annotators enhances annotation performance. While incorporating first-party demographic information into prompts leads to a marginal but statistically significant improvement in LLMs’ performance. We introduce a framework for evaluating the limitations of third-party annotations and call for refined annotation practices to accurately represent and model authors’ private states.