Conversational artificial intelligence is increasingly embedded in everyday social environments, where it functions as both an informational tool and a source of interpersonal feedback. This perspective introduces contingency, i.e., the degree to which system responses vary with user behavior and its interpersonal consequences, as a central construct for evaluating AI systems. We argue that current alignment approaches, including reinforcement learning from human feedback, tend to prioritize user approval and conversational fluency over behaviorally informative feedback, leading to sycophantic patterns of noncontingent affirmation. Drawing on behavioral science and social learning theory, we propose that contingent feedback is a key mechanism through which individuals develop interpersonal skills. When AI systems provide feedback weakly coupled to social consequences, they may reduce opportunities for adaptive calibration in real-world interactions, particularly during adolescence, a critical period for social development. We outline a framework for contingent AI, including trajectory-based evaluation and models of social consequence prediction, and propose a research agenda spanning developmental psychology, human-AI interaction, and machine learning. More broadly, we argue that AI systems should be evaluated not only by user satisfaction, but by their impact on human social learning.

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