Desirability Confirmation: Relational Sycophancy in AI Intimate Roleplay

AI sycophancy has become a prominent concern in large language model (LLM) research. Yet the term lacks a consistent definition and has been applied to behaviors ranging from agreeing with a user's false claim to excessively praising the user to withholding corrective feedback. When researchers, companies, and policymakers use the same term to describe different behaviors, evaluation results become difficult to compare, mitigation strategies fail to transfer, and systems that are resistant to one form of sycophancy continue exhibiting other forms. To address this, we make two contributions. First, we reviewed 70 papers on AI sycophancy to develop a taxonomy of how the behavior has been defined and measured. The taxonomy distinguishes (1) whether a model is sycophantic toward a user's positions and beliefs, or toward the user's broader personal traits and emotions, and (2) whether this occurs through explicit, direct language or more implicit, subtle behaviors such as framing, omission, or tone. Mapping existing literature to our taxonomy reveals that current research has focused on overt forms of sycophancy toward users' beliefs, leaving more subtle and person-directed behaviors relatively understudied. Second, we surveyed 106 experts in AI sycophancy and related fields to examine whether researchers agree on which model behaviors are sycophantic. While experts are nearly unanimous in believing that sycophancy is a significant problem in current AI systems (94.3% agree), they disagree substantially on which specific behaviors qualify. Together, these findings demonstrate that AI sycophancy is a broad family of behaviors with different measurement challenges, intervention requirements, and governance implications. Our taxonomy provides a shared vocabulary for understanding and addressing these behaviors.

Large language models increasingly serve as conversational agents that adopt personas and role-play characters at user request. This capability, while valuable, raises concerns about sycophancy: the tendency to provide responses that validate users rather than prioritize factual accuracy. While prior work has established that sycophancy poses risks to AI safety and alignment, the relationship between specific personality traits of adopted personas and the degree of sycophantic behavior remains unexplored. We present a systematic investigation of how persona agreeableness influences sycophancy across 13 small, open-weight language models ranging from 0.6B to 20B parameters. We develop a benchmark comprising 275 personas evaluated on NEO-IPIP agreeableness subscales and expose each persona to 4,950 sycophancy-eliciting prompts spanning 33 topic categories. Our analysis reveals that 9 of 13 models exhibit statistically significant positive correlations between persona agreeableness and sycophancy rates, with Pearson correlations reaching $r = 0.87$ and effect sizes as large as Cohen's $d = 2.33$. These findings demonstrate that agreeableness functions as a reliable predictor of persona-induced sycophancy, with direct implications for the deployment of role-playing AI systems and the development of alignment strategies that account for personality-mediated deceptive behaviors.

Sycophancy, where an LLM becomes overly agreeable, deferential, or flattering toward the user, has been identified as a major failure mode. While post-training has been implicated as a cause, how it internally gives rise to sycophantic behavior remains insufficiently understood. Post-training transforms the model's output from text completion into utterances directed toward an addressee, thereby giving the output addressivity. We hypothesize that the accompanying pressure to follow the addressee's instructions and align with their preferences links this addressivity to sycophancy. To test this, we use Sparse Autoencoders to extract addressivity directions from pre-trained and post-trained models and examine their relationship with sycophancy. Steering models with addressivity directions can amplify or suppress sycophancy, and this effect is observed only in post-trained models. Furthermore, comparing the internal mechanisms of both model types confirms that the association between addressivity and sycophancy is strengthened through post-training. Finally, through a controlled post-training experiment, we find that models are sycophantic not toward a specific addressee but toward any recognized addressee, suggesting that the presence of an addressee, rather than the addressee's identity, is what elicits sycophancy.