In an attempt to characterize men who pay women for sex (MPWS), theory and research generally divides men into two groups: men who pay for sex and those who never paid for sex. However, this dichotomy may lack sufficient detail to understand sex payment accurately, and with regard to attitudes toward paying for sex and frequency of sex payment. The present study set out to explore the associations between views toward MPWS; socio-demographic characteristics and frequency of paying for sex. A sample of 632 Israeli men, ages 18–75, were recruited via Facebook ads. Participants completed an anonymous, online questionnaire on their attitudes toward MPWS. Men who paid for sex once were more similar in their attitudes to men who did not pay for sex than to those who paid more than once. In addition, favorable views on MPWS predicted paying for sex only among men who paid for sex more than once, but not among men who paid for sex once. These findings may require new programmatic attention in public policy considerations and therapeutic strategies, taking into consideration both attitudes of men who pay for sex toward, and frequency of, this behavior.