Purpose of Review: Anhedonia is a transdiagnostic symptom comprising reduced subjective reward or pleasure. Anhedonia influences subjective anticipation and in-the-moment experiences. This review draws together affective learning and engagement evidence for anhedonia affecting subjective experiences of social environments. Recent Findings: While social engagement is diminished consistently, subjective appraisals of social contexts vary across different mental health disorders. Low positive affect during social experiences or stimuli is reported in PTSD, mood, schizophrenia, and anxiety disorders. Diminished neural reward networks underpin the anticipation of social experiences in ADHD, schizophrenia spectrum, and autistic spectrum disorders. Multiple theories exist to explain how anhedonia might interfere with social environments. Summary: Anhedonia is a barrier to engagement, motivation, and enjoyment of social contexts. While many studies characterize experiences during social contexts, learning theories provide the most promise for developing targeted interventions.