In contemporary educational discussion, concerns have been raised about the influence of the so-called post-truth era and its impact or consequences on democratic education. Facing these challenges calls for more discussion concerning the role of truthfulness and honesty as central parts of democratic education. In this essay, we argue that while truthfulness and honesty are essential features of democratic education, some gray areas concerning their consequences need to be scrutinized. When put in the context of education, ideals of truthfulness and honesty should be considered from the perspective of educational responsibility of protecting students. We participate in a broad discussion that is essential to any attempt to educate democratic citizens by asking how we can better support students' hope for the future and democracy through education. Based on our philosophical analysis, we suggest that what we call 'regulated (dis)honesty' may be justified and beneficial in democratic education for the future of pluralistic democratic societies.