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A relationship without trust is invariably tenuous and vulnerable to challenges that cause it to fail. For this reason, the long legacy of distrust between Cuba and the United States may be the most significant problem the two countries face in trying to build “normal relations”. However, constructive bilateral engagement - through educational exchanges - builds trust and creates spaces for empathy. Exchanges mitigate estrangement created by bilateral hostilities and generate a better understanding of both countries’ political culture, legal framework, and rule of law. For a long time, public diplomacy and educational programs have linked individuals, groups, institutions and nongovernmental organizations and have been the path to break down barriers that separate cultures and communities. This paper analyzes the role of educational exchanges in breaking down stereotypes and constructing a better cultural understanding between two societies. From the personal perspective of a young Cuban woman studying in the United States, the paper addresses 1) the main challenges and cultural differences for Cuban students in the U.S., 2) the divergences in university education systems between the two countries and 3) how the educational experience is translated into future professional careers and could contribute to the development of better societies.