Background: Dysmenorrhea and premenstrual syndrome (PMS) are common disorders in the Mexican population, but these are usually underdiagnosed and under-treated, impacting women’s quality of life. Adequate health habits have been reported as precursors of decreasing dysmenorrhea symptoms. However, few studies assess their impact on PMS. Aim: This study aims to evaluate dysmenorrhea and premenstrual syndrome in association with health habits in the Mexican population. Methods: To assess the impact of health habits on menstruation symptoms a validated survey was conducted in 1679 adult females aged ≥18 years. The survey collected data on participants’ dysmenorrhea, PMS, and their health habits. Results: The analysis showed that physical activity duration, changes in eating habits (increases in salty or sugary foods) during menstruation, and oversleeping habits predict increases in dysmenorrhea and PMS. In contrast, an active sexual life, relaxing physical activity, and adequate sleep hours during menstruation seem to decrease the symptoms. Conclusions: We conclude that adequate health habits and addressing early gynecological conditions might regulate dysmenorrhea and PMS.