Background: This study aimed to determine the prevalence of symptomatic dry eye among medical students and identify associated demographic and psychological factors. Methods: A cross-sectional online survey was conducted among medical students enrolled at Jordanian universities during September 2025. Participants completed a structured electronic questionnaire including demographic and lifestyle characteristics, the validated Perceived Stress Scale-10 (PSS-10), and the validated Ocular Surface Disease Index (OSDI). Univariable and multivariable logistic regression were used to identify factors associated with severe symptomatic dry eye. Results: A total of 311 medical students participated. The mean OSDI score was 34.84 ± 18.18, with 54.7% classified as having severe symptomatic dry eye. In multivariable logistic regression, perceived stress was associated with severe symptomatic dry eye after adjustment for measured covariates (adjusted OR = 1.056, 95% CI: 1.015–1.098, p = 0.007). Higher perceived stress was also associated with greater symptom severity (p = 0.001) and higher OSDI scores after adjustment (p = 0.010). Conclusions: Symptomatic dry eye symptoms were highly prevalent among medical students, and perceived stress was associated with greater symptom burden and severity after adjustment for measured covariates. These findings highlight the potential relevance of stress-related factors to ocular symptoms among medical students and encourage further investigation.