Introduction: Psychological well-being is recognized as an important health component, which influences the behavior, ability to cope with stressful events, work performance, and generally the ability to achieve one's full potential. Aim: To comparatively assess the psychological well-being of dental students during the summer semester examination period and summer holiday. Material and methods: A single-arm, prospective study was conducted in second year dental students from the Faculty of Dental Medicine, Bucharest. The psychological well-being was assessed using the WHO-Five Wellbeing Index. Results: Students' psychological well-being was statistically significantly better during the summer holiday (median= 19) than during the summer semester examination period (median= 11.5), Z= 3.69, p <. 001. The perceived satisfaction regarding financial means, faculty colleagues, home, family and overall life satisfaction was the same during summer semester examination period and summer holiday, but it was significantly correlated with the WHO-Five Well-being Index score corresponding to the summer holiday, and no association was observed with the WHO-Five Well-being Index score corresponding to the summer semester examination period. Conclusions: Within the limits of this study, psychological well-being is likely to be negatively influenced, on a fairly large scale, by the semester examination period. Therefore, it is recommended to identify the most appropriate methods of examination with regards to the psychological load that might be a threat to the validity of students' evaluation. Additionally, training students about adequate coping strategies, designed as interventions at individual or group level, may be required.