Thailand has undergone rapid modernization with implications for changes in sexual norms. We investigated sexual behavior and attitudes across generations and gender among a probability sample of the general population of Nonthaburi province located near Bangkok in 2012. A tablet-based survey was performed among 2,138 men and women aged 15–59 years identified through a three-stage, stratified, probability proportional to size, clustered sampling. Descriptive statistical analysis was carried out accounting for the effects of multistage sampling. Relationship of age and gender to sexual behavior and attitudes was analyzed by bivariate analysis followed by multivariate logistic regression analysis to adjust for possible confounding. Patterns of sexual behavior and attitudes varied substantially across generations and gender. We found strong evidence for a decline in the age of sexual initiation, a shift in the type of the first sexual partner, and a greater rate of acceptance of adolescent premarital sex among younger generations. The study highlighted profound changes among young women as evidenced by a higher number of lifetime sexual partners as compared to older women. In contrast to the significant gender gap in older generations, sexual profiles of Thai young women have evolved to resemble those of young men with attitudes gradually converging to similar sexual standards. Our data suggest that higher education, being never-married, and an urban lifestyle may have been associated with these changes. Our study found that Thai sexual norms are changing dramatically. It is vital to continue monitoring such changes, considering the potential impact on the HIV/STIs epidemic and unintended pregnancies.