Investigation of the European Union’s foreign policy towards Hamas acquires its significance as a topic from the undemocratic way in which the (supposedly) democratic EU pursues its strategy since, according to its own rhetoric, this should have been normatively undertaken. In examining inconsistencies and paradoxes in the EU discourse towards Hamas, and the determinants underlying such contradictions, the study scrutinizes questions of ‘how’ and ‘why’, focusing mainly on identities and self-interests as lenses borrowed from constructivism and neorealism, as well as the influence of external actors on the way the EU functions towards Hamas. Behind such inconsistency stands a cultural-historical heritage, part of the mind-set of the European decision-makers. The contradictory status of the association between the two actors is formed by the main interactively-constructed and conflictual socio-political components arising from the reality of the EU as a stability-seeking and security-driven actor in Palestine, and the self-definition of Hamas as a freedom-fighter striving for the liberation of its lands. Being defenders of the culturally-drawn meanings given by the EU to Palestine as a ‘promised land’ for the Jews within a two-state solution, and those given to it by Hamas as an ‘Islamic Waqf’ is another field of identities’ clash between the two actors. The Israeli factor, regarded in practice as a fixed, constant and purely Western and European interest in the Middle East, along with the dominant influence of the US on its EU partner, are emphasized as main determinants of EU policy towards Hamas. On the macro and micro levels, the determinants of the EU decision making process, and the way the EU functions when its perceived interests are threatened must be understood when any decision on relations with the EU is taken, particularly by the Palestinian resistance factions. At the same time, the EU should also examine its own inconsistencies in dealing with Hamas as a ‘terrorist’ organization and boycotting its democratically-elected government, in order to avoid repeating the ‘trial and error’ approach with the new powers rising in the ‘Arab spring’ countries, and to adapt itself to change in Palestine accordingly.