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Objective: Social anxiety disorder (SAD), (also known as social phobia), is characterized by intense fear of social interaction and often associated with social avoidance and impairments. There is high risk for depression, substance use disorder, and suicide among them. Subjects and Methods: It is an observational, cross-sectional, single centered, questionnaire-based study assessing the frequency of SAD and depression and their possible association with quality of life among 290 consenting medical undergraduate students. Social Phobia Inventory (SPIN), Beck's Depression Inventory (BDI II), and the World Health Organization Quality of Life assessment scale (WHOQOL-BREF) were used to screen and assess severity of SAD, depression, and quality of life, respectively. The statistical analysis of proportions was done by Chi-square test, while the scores of SPIN, BDI II, and WHOQOL-BREF was compared using Mann–Whitney test or Kruskal–Wallis test followed by Dunn posttest multiple comparison, using GraphPad InStat version 3.06. Results: Frequency of SAD is 11.37%, and depression is 8.96%. Females are more likely to experience SAD. Participants with SAD are more likely to experience depression (P < 0.0001) and have poor quality of life (P = 0.01). Participants with depression have higher SPIN score (P < 0.0001) and poor quality of life (P < 0.0001). Females are more likely to experience social fear (P = 0.02). Participants staying away from their family are more likely to experience social anxiety in comparison to their peers (P = 0.01). Severity of depression is correlated with severity of social anxiety (Spearman r = 0.4423 [0.3416–0.5329], P < 0.0001). Conclusion: Participants with SAD are more likely to experience depressive symptoms and have poor quality of life and vice versa.