A growing number of women of reproductive age experience menstrual disorders. The menstrual cycle is considerably influenced by dietary habits, physical activity, and the use of stimulants. The main aim of this study was to assess women’s knowledge about the menstrual cycle and the influence of diet and lifestyle factors on menstrual symptoms, and to identify dietary models that may alleviate or exacerbate menstrual distress. A total of 505 young women participated in the study. Nearly 90% of the respondents reported at least one menstrual disorder, mostly dysmenorrhea (70.7%), whereas secondary amenorrhea was least frequently reported (13.8%) (p = 0.002). In the study population, dysmenorrhea/menstrual distress was linked with higher consumption frequency of certain food groups. Women with severe dysmenorrhea consumed refined cereal products, processed meat, sugar, and water significantly more frequently than women with moderate menstrual pain. In turn, sweetened dairy products, animal fats, and fruit were consumed more frequently by women with low intensity of menstrual pain (mild pain). Significant differences in knowledge about the menstrual cycle and physiological changes in the body were observed between the compared dietary models.