This paper depicts the dynamics of the EU-Turkey relations beginning from the signing of the association agreement, i.e. the Ankara contract, to date. In addition, it aims to specify the factors preventing the bilateral collaboration and achievement of EU membership as aspired to by Ankara. The paper focuses on both the internal and international problems arising on Turkey's path to EU membership, namely, the westernisation trend originating from Kemal Ataturk times, recent developments in Turkey, the democratisation of political institutions, the rule of law and protection of human rights, regional security, Turkey's part in the refugee crisis, visafree travel, Greek-Turkey relationships, Ankara's stance towards Cyprus, the Kurdish problem, and the Turkey-US and Turkey-Russia relationships. The authors discuss the EU Member States' attitude towards the political and socio-economic developments in Turkey and the way Ankara looks at the requirements put forward by those Member States. We suggest several methods of rapprochement and brighter bilateral prospects.