Despite the value of assessing opinion expression in free and consolidated democracies, exploring the willingness of opinion expression in non-democratic settings remains limited. Examinations of people’s communication behaviors under alternative political regimes can help demonstrate if the exchange of opinions online might engender alternative political impacts in settings where citizens may desire greater levels of political engagement. This study compares opinion expression in incongruent offline and online settings on the issue of gender desegregation in Kuwait’s public schools. Given the competing social perspectives that exist, gender desegregation is an issue that wields strong opinions on either side of the debate, though a conservative view currently predominates publicly. The Spiral of Silence theory provides the foundation for examining the impact of cultural conformity, religiosity, Twitter-use variables, and traditional SOS theoretical components, including the fear of social isolation and perceptions of current and future opinion climates, on Kuwaitis’ willingness to express their opinions both offline and online. Based on a questionnaire administered to 534 public and private university students, multiple regressions and analyses of variance tests were performed which demonstrated that, overall, most people preferred to express opinions in offline rather than online settings. Some people who are characteristically expressive offline continued to be so online, but more often, those who use Twitter frequently moderated their opinion expression. Other respondents were more interested in reading opinions on Twitter than they were in expressing their own. Offline and online, the nonconformist personality variable was a positive predictor of opinion expression. Fear of social isolation was not only a negative predictor of offline opinion expression, but it was the strongest of all predictors. Two additional impediments to offline opinion expression were identification of religious certainty and the fear of social isolation, demonstrating the substantial impact of dominant cultural norms on opinion expression. From these results, it seems that on the issue of gender desegregation, in a Kuwaiti context at least, the Twittersphere does not appear to be facilitating a more robust public debate of the type that might provoke a reevaluation of the status quo. Rather it appears to be contributing the opposite effect.