The present research examines men’s self-conscious discomfort while imagining performing counter-stereotypical (traditionally feminine) behaviors as compared to stereotypical (traditionally masculine) behaviors, as a function of traditional masculinity endorsement and perceived social changes in men’s gender norms (men’s feminization) in two distinct cultural populations (U.S. Americans and Kosovan Albanians). Experiment 1 (n = 192, U.S.) confirmed prior findings by showing that men, as compared to women, experienced more self-conscious discomfort when imagining performing counter-stereotypical (vs. stereotypical) behaviors. Experiments 2 (n = 292, U.S.) and 3 (n = 191, Kosovo) focused solely on heterosexual men and experimentally manipulated perceived social changes in men’s gender norms. Results showed that the men’s feminization condition, as compared to a control or masculinity conditions, decreased self-conscious discomfort when imagining performing feminine behaviors among men who endorsed a lower versus higher level of traditional masculinity. Experiment 3 further indicated that this effect was driven by lowered expectations of being misclassified as gay. We discuss the relevance of these findings for both the gender and sexual prejudice literature.