This article draws on the philosophical work on dialogic rationality offered by Charles Taylor as well as qualitative studies of dialogues between politically opposed college students to argue that these conversations succeed as tools of democracy precisely because they fail as interventions. That is, the democratic strength of such dialogue is the way in which it is unreliable as a means of producing particular outcomes. Students whose political views eventually shifted partly in response to dialogue understood this not as a process of changing their commitments, but rather of finding a better expression for the commitments they already held. But the interviews show, too, just how rare it is for such shifts to occur at all, at least for these students in a period of political polarization and mutual distrust. The interviews suggest as well that the appeal to already shared ground is not the whole story of what prompts people to change their minds in these kinds of conversations. Rather the asking of direct but respectful questions was a crucial ingredient. Finally, dialogue did not independently cause the most profound changes in political views. Instead, it was the direction of students' lives that over time shifted their outlook. Their dialogue experience then gained meaning in retrospect, as the beginning of a process of self-questioning that was brought to fruition only later, as a first time that they had heard alternative possibilities for how value commitments can be expressed through politics.