Cheek biting is a chronic, usually innocuous, self-inflicted injury that often occurs as a parafunctional habit. We report an unusual case of bilateral cyclic cheek lesions in a 34-year-old woman characterized by hyperkeratinization near the biting edges of the teeth and hematic lesions accompanied by a cheek swelling sensation, without pain and burning. The lesions coincided with a premenstrual syndrome, characterized by fluid retention-related symptoms, such as leg swelling, breast tenderness, bloatedness with abdominal girth variation and weight gain. We concluded that the excessive water retention caused a little widespread swelling, present at cheeks level also, that associated with a temporary bruxism (perhaps related to psychological stress typical of premenstrual syndrome) was probably responsible for the cyclic cheek lesions. Therefore, an oral exam by the womens health care provider may be valuable in cases of premenstrual syndrome.