Hostility toward women is an established risk factor for sexual violence and is often found to be present in men prone to sexual transgression. There are also clinical indications that high-risk rapists may have more ambivalent attitudes toward women, including the strong desire to be positively evaluated by women. We investigated attitudes toward women in high-risk male rapists (n = 42), nonsexual male offenders (n = 65), and matched male community controls (n = 42), by means of self-report (hostility toward women, benevolent sexism, hostile sexism) and implicit measures assessing associations (Implicit Association Test [IAT]) with “women are deceitful” and “women are prestige objects,” and the approach tendency (Approach–Avoidance Task [AAT]) toward women. Results showed that high-risk rapists had a lesser implicit notion of women as deceitful and more explicit benevolent sexism than the community controls. These differences seemed most prevalent in the subgroup of high-risk rapists without any relationship history. It is hypothesized that unrealistically positive attitudes toward women may lead to rejection and frustration, which may influence sexual offending.