In 2019 Poland will celebrate the centennial anniversary of the establishment of Polish-U.S. diplomatic relations and the 30th anniversary of freedom from communist rule, making this an opportune time to compare Polish and American views of freedom, liberty, and democracy. Using data from the World Values Survey, waves 2 through 6 (1989-2014), this paper examines diversity in public opinion on a range of freedom issues, including democracy, women’s rights, immigrants’ rights, civil liberties, freedom of speech and of religion, and human rights, with a particular focus on gender diversity. Findings show considerable variation between U.S. men and women – but not Polish men and women – on freedom-related attitudes and beliefs. Cross-country comparisons show that, with some exceptions, U.S. men and women tend to express more liberal ideas, though Poles’ views are becoming more progressive over time. We conclude that a gender perspective is essential to a full understanding of comparative attitudes toward democracy, liberty, and freedom.