<p>This study explores how gender role discrepancy (GRD) and social media addiction mediate the relationship between social phobia and psychological distress among Gen X, Y, and Z. An online structured questionnaire administered to 700 men aged 18–63 revealed mostly similar patterns across generations. Positive direct effects of social phobia on psychological distress were found in all three generations, with positive associations also observed between social phobia and GRD, GRD and social media addiction, and social phobia and social media addiction. Social media addiction positively correlated with psychological distress across all generations. Notably, the positive correlation between GRD and psychological distress was significant for Gen X and Y but not for Gen Z, suggesting emerging flexibility in masculine gender norms. This study highlights the persistence of traditional gender norms in shaping psychological outcomes, indicating that while younger generations show some shifts towards flexibility, entrenched gender roles continue to be a significant factor in psychological distress across all generational cohorts. Addressing both GRD and social media addiction is crucial in developing effective interventions for psychological distress. The findings offer practical implications for designing mental health and workplace strategies that are sensitive to generational differences among men.</p>