Background Primary dysmenorrhea is a common and often debilitating, gynaecological condition. Objective To investigate the effects of specific lifestyle variables on the prevalence and severity of primary dysmenorrhea. Materials and Methods A cross-sectional study of Jordanian women aged between 18–25 years old utilized a questionnaire as the main instrument of the study. Results Primary dysmenorrhea was reported by 660 women out of 1988. It was found that approximately two thirds of them were students. Overall, 54.5% of the participants reported severe dysmenorrhea. A statistically significant correlation was found between severe dysmenorrhea and smoking at p value ˂0.001, sleeping less than 7 hours per 24 hours at p = 0.005, holding a university degree at p = 0.032, non-alcohol consumption at p = 0.044, frequent energy, fizzy, tea, coffee drinks and sugar intake. Interestingly, we found that severe dysmenorrhea was statistically significantly associated with women who never eat meat at p ˂0.001, cereals and fish consumers and with those who take less than 3 servings of fruit or none at all per week at p = 0.006. In addition to the previous variables, water intake of less than 1.0 litre a day, irregular cycles, non-OCP use and positive family history were found significantly associated with severe dysmenorrhea. Severe dysmenorrhea was significantly related to working less hours per week, higher stress level and longer bleeding duration at p = 0.021, 0.017 and 0.008, respectively. On the other hand, there was no statistically significant difference found between severe dysmenorrhea and the following variables: age, body mass index (BMI), weekly studying hours and age of menarche. Conclusion Primary dysmenorrhea is prevalent in the Jordanian population. To overcome severe dysmenorrhea, women should increase their intake of fish and fresh fruits, drinking water and use of oral contraceptive pills. The study concluded that smoking, frequent sugar intake, fizzy drinks, coffee, tea and energy drinks were associated with severe dysmenorrhea. It is also worth mentioning that alcohol consumption had a positive impact on dysmenorrhea. Trial Registration Registered in Clinicaltrial.gov (ID: NCT04583943).