A qualified Chinese dental postgraduate requires at least eight years of training. The huge academic burden, strict clinical requirements, and high workload increases the risk of job burnout, depression symptoms, and career choice regret of dental postgraduates, which may cause one to waver in their choice of a career as a doctor. Therefore, we aimed at assessing the relationship between job burnout, depressive symptoms, and career choice regret among Chinese dental postgraduates. The Chongqing Stomatological Association conducted an online cross-sectional study among 558 dental postgraduates in China, with an average age of 22.54 ± 2.44. Demographic information, the Maslach Burnout Inventory, the 2-item Primary Care Evaluation of Mental Disorders scale, and career choice regret scale were included in the questionnaire. About 41.0% of dental postgraduates experienced job burnout, 44.1% had depressive symptoms, and 41.6% reported career choice regret. Logistic regression analysis indicated the risk factors for job burnout were time worked/studied per week, depressive symptoms, and career choice regret. Job burnout and career choice regret was significantly related to depressive symptoms (p < 0.001). Risk factors for career choice regret were gender, postgraduate entrance examination score, daily hours of sleep, job burnout, and depressive symptoms. Such results suggest that job burnout, depressive symptoms, and career choice regrets are prevalent among dental postgraduates. Accurate measures should be taken to change this situation.