Introduction: Dysmenorrhea is defined as the presence of painful menstruation, and it affects daily activities in different ways. The aims of this study were to assess the prevalence and management of dysmenorrhea and to determine the impact of dysmenorrhea on the quality of life of medical students. Material and methods: The study conducted was prospective, analytical and observational and was performed between 7 November 2019 and 30 January 2020 in five university centers from Romania. The data was collected using an original questionnaire regarding menstrual cycles and dysmenorrhea. The information about relationships with family or friends, couples’ relationships and university activity helped to assess the effects of dysmenorrhea on quality of life. The level of significance was set at p < 0.05. Results: The study comprised 1720 students in total. The prevalence of dysmenorrhea was 78.4%. During their menstrual period, most female students felt more agitated or nervous (72.7%), more tired (66.9%), as if they had less energy for daily activities (75.9%) and highly stressed (57.9%), with a normal diet being difficult to achieve (30.0%). University courses (49.4%), social life (34.5%), couples’ relationships (29.6%), as well as relationships with family (21.4%) and friends (15.4%) were also affected, depending on the duration and intensity of the pain. Conclusion: Dysmenorrhea has a high prevalence among medical students and could affect the quality of life of students in several ways. During their menstrual period, most female students feel as if they have less energy for daily activities and exhibit a higher level of stress. The intensity of the symptoms varies considerably and, with it, the degree of discomfort it creates. Most student use both pharmacological and non-pharmacological methods to reduce pain (75.7%). University courses, social life, couples’ relationships, as well as relationships with family and friends are affected, depending on the duration and intensity of the pain.