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Masculine norms are in part defined by sexual functioning. However, adherence to masculine norms may at the same time hinder men’s willingness to obtain help when problems involving sexual functioning arise. The current study analyzed the association between gender role conflict and the prevalence of self-reported sexual dysfunction or men’s expectations of being asked by a physician about sexual health issues. In all, 130 men (Mage = 59.4, SD = 14.6) participated in the study. In a structured interview, they were asked to self-report the prevalence of sexual dysfunctions. The criterion of distress was also given consideration. The frequency of previous conversations with a physician about sexual health issues and the desire to be asked in future about sexual health issues were assessed by administering a questionnaire. The Gender Role Conflict Scale–Short Form was used to measure gender role conflict. The most prevalent sexual dysfunctions were erectile dysfunction (10.0%), diminished sexual desire (7.7%), and premature ejaculation (4.6%). The prevalence of erectile dysfunction and diminished sexual desire was positively associated with restrictive emotionality. Premature ejaculation was positively associated with men’s restriction about showing positive affection toward other men. Overall, men expected their physicians to ask them about their sexual health. Restrictive emotionality was positively associated with the disinclination to be asked about this topic. Physicians should be aware of the close association between masculinity and sexual functioning. When asking about sexual health issues, physicians should be sensitive to patients’ gender role conflict and attempt to create a gender-sensitive environment.