Social functioning relies on effectively balancing social approach and avoidance behaviors. maladaptive, exaggerated social avoidance constitutes a risk factor for the development of social anxiety disorder. To explore how people learn from social experiences in a naturalistic yet controlled setting, we developed an immersive virtual environment that combines a social conditioning procedure with a social approach-avoidance test previously applied in animal research. In two experiments (both N = 48) we investigated how participants with varying levels of trait social anxiety adapt their approach and avoidance tendencies toward conditioned virtual agents. We examined adaptations in the behavior (whole-body movements, interpersonal distance), visual exploration (gaze behavior), and subjective experience (perceived likeability, fear, and anger), alongside autonomic measures (pupil dilation, electrodermal activity, and heart rate). Across the experiments, we found that the social conditioning procedure significantly influenced participants’ exploration behaviors, including interpersonal distance and spontaneous fixations, as well as their subjective evaluations of the virtual agents. Although autonomic responses varied during the social encounters, no long-term physiological adaptations persisted during the social approach-avoidance test. Importantly, trait social anxiety was associated with higher fear ratings and increased interpersonal distance. This study demonstrates the potential of immersive virtual environments for examining social learning processes under conditions resembling real-life social encounters.