This chapter explores the first major steps in the relationship between the European Union (EU) and Romania, culminating in the start of entry negotiations in 2000 and the return to power in 2001 of the Social Democratic Party, which would be the chief Romanian interlocutor with the EU over the next four years. Ion Iliescu's strategy of cautious democratisation without meaningful de-communisation remained largely intact. Progress with the EU application appeared to be the most realistic option for strengthening ties with the West. The EU's institutions of multilevel governance proved remarkably prone to lobbying from the Romanian state and the allies it had meanwhile cultivated in Western Europe in order to advance its cause. The 1999–2000 medium-term economic strategy proved to be an ephemeral document and the EU failed to prioritise vital areas such as administrative reform. The EU's multi-layered decision-making system failed to produce a hard-headed cost-benefit analysis.