Recent evidence suggests that voluntary rhythmic movements such as chewing may increase blood serotonin and subsequently brain serotonin, which in turn acts to alleviate premenstrual symptoms. In this observational cross-sectional study, we tested the hypothesis that hardness (difficulty of chewing) of the habitual diet (i.e. dietary hardness) is associated with decreased premenstrual symptoms. Subjects were 640 female Japanese dietetic students aged 18–22 years. Dietary hardness was assessed as an estimate of masticatory muscle activity for the habitual diet (i.e. the difficulty of chewing the food). The consumption of a total of 107 foods was estimated by means of a self-administered, comprehensive diet history questionnaire, and masticatory muscle activity during the ingestion of these foods was estimated according to published equations. Menstrual cycle symptoms were assessed using the retrospective version of the Moos Menstrual Distress Questionnaire, from which total score and subscale scores (i.e. pain, concentration, behavioral change, autonomic reactions, water retention, and negative affect) in the premenstrual phase were calculated and expressed as percentages relative to those in the intermenstrual phase. Dietary hardness was not associated with total score in the premenstrual phase (P for trend = 0.48). Further, no association was seen for any subscale score in the premenstrual phase (P for trend = 0.18–0.91). In conclusion, this preliminary study failed to substantiate a hypothesized inverse relationship between hardness of the habitual diet and premenstrual symptoms. Considering the plausibility of the putative mechanism, however, further investigation using more relevant measures of chewing and premenstrual symptoms is warranted.