All human experience is situated in specific sociocultural and political contexts that profoundly shape that which we know and that which we cannot know. In this article, I use my personal experience of traveling to Cuba as a U.S. citizen, in violation of the U.S. embargo against Cuba, to reflect on the consequences of severing dialogue. I argue that dialogue expands my understanding of my situatedness by exposing the gap between the person I was shaped be by virtue of my throwness, and the person I aspire to be based upon my own value system. I conclude that in the process of making an ethical claim on a person who seeks understanding, dialogue also expands one’s possibilities for meaningful existence.