Dysmenorrhea is a monthly menstrual pain that can limit a woman’s quality of life (QOL). The relationship between dysmenorrhea severity and QOL has been reported in several countries; however, the results cannot be generalized because lifestyle and cultural background affect menstrual pain. This study sought to uncover whether 1) different factors, such as emotions and ways of coping with symptoms, vary with the severity of dysmenorrhea and 2) the severity of dysmenorrhea ultimately affects QOL in Japan. A web-based cross-sectional survey was sent to 1000 Japanese females aged 16–30 years. The respondents were divided into two groups: those without dysmenorrhea (n = 24) and those with dysmenorrhea (n = 471). The severity of dysmenorrhea was classified using the Numerical Rating Scale as either mild (1–3), moderate (4–7), or severe (8–10). In total, 156 respondents reported mild dysmenorrhea, 249 reported moderate dysmenorrhea, and 66 reported severe dysmenorrhea. QOL was measured using the 26-item World Health Organization Quality of Life scale. One-way ANOVA and Kruskal-Wallis tests were used to compare QOL across different levels of dysmenorrhea severity, depending on normality. Ultimately, significant differences in QOL scores (p<0.001) were observed based on dysmenorrhea severity, with respondents with severe dysmenorrhea reporting the lowest QOL scores. Meanwhile, significant differences were observed in the physical, psychological, and environmental subscales (p<0.001, p<0.001, p = 0.019) across respondents with different levels of dysmenorrhea severity; notably, respondents with severe dysmenorrhea demonstrated a negative spiral of chronic pain, which may significantly impact QOL, and, relatedly, a relatively low psychological QOL. This study is the first to show the relationship between dysmenorrhea severity and QOL in Japanese females, who are more likely to experience negative feelings during menstruation.