Since the 1980s an increasing number of international actors have been promoting democracy worldwide using different methods and instruments. However, despite initial successes, many of these newly created democracies remain weak and have failed to consolidate the process. The European Union was most effective in Southern and Eastern Europe during the 1980s and 1990s, and has since developed further initiatives to promote democracy on a wider scale. My investigation contributes to this literature by studying the European Union’s promotion of democracy in Latin America between 1995 and 2005. This region had begun a linear transition toward democracy, but, after more than two decades, it is still unable to capitalise and consolidate its progress. The methodology focuses on the study of the relationship between the donor and the recipient and how such relationship influenced the strategy and impact of the donor’s policies. A set of conditions has been selected in order to evaluate the nature of the relationship. This work examines some case studies of EU initiatives promoting democracy in three Latin American countries - Costa Rica, Peru, Uruguay. The strategy adopted in Costa Rica was heavily influenced by the 'Dialogue of San José' and the democratic development of the recipient country. Since Costa Rica enjoyed some political stability the Union’s sub-regional policies could be implemented by Costa Rican-based organisations and their impact proved successful thanks to the support of both domestic political and civil society organisations. On the contrary, the absence of effective political dialogue between Peruvian authorities and the Union from 1995 to 2000 meant that only few small-scale EU initiatives were implemented. However, once stronger political dialogue had been established, in 2001-2005, the initiatives increased in dimension and they were more visible. Finally, in Uruguay very few democracy promotion programmes were applied. Although political and economic agreements were signed between the Union and Uruguay, via the inter-regional dialogue EU-MERCOSUR, Uruguay did not benefit from large-scale programmes due to the relatively advanced level of democracy throughout MERCOSUR. To conclude, I argue that the European Union’s programmes in these Latin America countries were influenced by the nature of the relationship between donor and recipient. The evidence suggests that the Union was not capable of enforcing sustainable democratic initiatives without the support of domestic actors.