The present study tested sex as a moderator of the connections between men’s and women’s masculine gender role strain (i.e., masculine gender role conflict and masculine gender role stress) and attitudes toward psychological, physical, and sexual male-perpetrated dating violence. Self-report measures were administered online to a large sample of male (n = 398) and female (n = 390) college students, and data were analyzed using structural equation modeling (SEM) procedures for testing moderation through measurement and structural invariance. In the measurement model for both men and women, masculine gender role stress was associated with acceptance of each form of dating violence acceptance, but only the restricted emotionality and restrictive same-sex affectionate behavior domains of masculine gender role conflict evidenced significant relationships with dating violence acceptance. In the structural model, where dating violence attitudes were regressed onto gender role strain constructs simultaneously, only masculine gender role stress emerged as a significant predictor of acceptance of each form of dating violence in the male sample and acceptance of physical and sexual violence in the female sample. Additionally, the direct associations between masculine gender role strain and dating violence acceptance attitudes were statistically invariant across men and women, although certain regression coefficients were statistically significant for men but not for women. The present findings support a small but growing body of literature examining women’s masculine gender role strain and highlight the importance of studying the combined contributions of different forms of gender role strain with respect to dating violence attitudes.